Photo-generated carbohydrate arrays and the rapid identification of pathogen-specific antigens and antibodies

• US 20100331198A1
• Filed: 09/11/2007
• Published: 12/30/2010
• Est. Priority Date: 09/11/2006
• Status: Active Grant

• Current Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Original Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Inventors: Turro, Nicholas J., Koberstein, Jeffrey T., Wang, Denong, Carroll, Gregory T.
• Granted Patent: US 8,658,573 B2
• Time in Patent Office: Days
• US Class Current: 506/9
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C40B 40/12 Libraries containing saccharides or polysaccharides, or derivatives thereof
• CPC Class Codes: C40B 50/18 using a particular method of attachment to the solid support
• CPC Class Codes: G01N 2333/32 from Bacillus (G)
• CPC Class Codes: G01N 2400/00 Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
• CPC Class Codes: G01N 2500/02 Screening involving studying the effect of compounds C on the interaction between interacting molecules A and B (e.g. A = enzyme and B = substrate for A, or A = receptor and B = ligand for the receptor)
• CPC Class Codes: G01N 33/56911 Bacteria

Abstract

The invention relates to novel photo-generated carbohydrate arrays and methods of their use to detect the presence of one or more agents in a sample. The invention also relates to a high-throughput strategy to facilitate the identification and immunological characterization of pathogen-specific carbohydrates, including those of Bacillus anthracis. The invention can be used to determine the presence of a pathogen and whether a subject has been exposed to a pathogen, such as by screening for pathogen-specific antibodies.

Claims

1. An array comprising:

a surface;

a compound of formula (I);

2. The array of claim 1, wherein the agent is a biomarker for a disease.

3. The array of claim 1, wherein the agent is an antibody.

4. The array of claim 3, wherein the antibody is capable of binding to a specific pathogen.

5. The array of claim 4, wherein the pathogen is Bacillus anthracis.

6. The array of claim 1, wherein n is an integer from 1 to 20.

7. The array of claim 1, wherein the compound of Formula (I) is

8. The array of claim 1, wherein at least one carbohydrate is selected from the group consisting of:

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-α

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside,

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranoside;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

or

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose,

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tetrakis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₅-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

glycosides thereof; and

combinations thereof.

9. The array of claim 1, wherein the compound of formula (I) forms a self-assembled monolayer.

10. A method for determining the presence of a pathogen or for diagnosing a disease in a subject, the method comprising the steps of:

exposing the array of claim 1 to a sample from a subject; and

determining the presence of the agent bound to one or more of the carbohydrates, wherein the presence of a bound agent indicates the presence of a pathogen in the sample.

24. The array of claim 1 or claim 11, wherein the array comprises a chip, a plate, a sensor, a slide, a combination thereof, or a portion thereof.

25. The array of claim 1 or claim 11, wherein the surface comprises an inorganic material.

26. The array of claim 25, wherein the surface comprises silica, glass, quartz, silicon, titanium, titania, gold, or a combination thereof.

27. The array of claim 1 or claim 11, wherein the surface comprises an organic material.

28. The array of claim 27, wherein the surface comprises polyacrylamide, nylon, polyethylene, polypropylene, PTFE, polycarbonate, polystyrene, poly(tert-butyl acrylate), poly(vinyl alcohol), nitrocellulose, or a combination thereof.

11. An array comprising:

a surface;

a compound of Formula (I) immobilized on the surface;

12. The array of claim 11, wherein Y is —

NH₂.

13. The array of claim 12, wherein the compound of Formula (III) and the compound of Formula (I) are present in a ratio from about 1:

1 to about 100;

1.

14. The array of claim 13, wherein the ratio is from about 5:

1 to about 20;

1.

15. The array of claim 11, wherein the agent is a biomarker for a disease.

16. The array of claim 11, wherein the agent is an antibody.

17. The array of claim 16, wherein the antibody is capable of binding to a pathogen.

18. The array of claim 17, wherein the pathogen is Bacillus anthracis.

19. The array of claim 11, wherein n is an integer from 1 to 20.

20. The array of claim 11, wherein the compound of Formula (I) is

21. The array of claim 11, wherein the compound of Formula (III) is

22. The array of claim 11, wherein at least one carbohydrate is selected from the group consisting of:

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-α

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1-6)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1-6)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranoside;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

or

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose,

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tetrakis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₅-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

glycosides thereof; and

combinations thereof.

23. The array of claim 11, wherein the compound of formula (I) or the compound of formula (III) or both form a self-assembled monolayer.

29. A method for determining the presence of a pathogen or for diagnosing a disease in a subject, the method comprising the steps of:

exposing the array of claim 11 to a sample from a subject; and

determining the presence of the agent bound to one or more of the carbohydrates, wherein the presence of a bound agent indicates the presence of a pathogen in the sample.

30. The method of claim 29, wherein the agent is an antibody.

31. The method of claim 30, wherein the pathogen is Bacillus anthracis and the antibody is an antibody to Bacillus anthracis.

32. A method for making an array, the method comprising the steps of:

forming on at least a part of a surface a self-assembled monolayer comprising a compound of formula (I);

33. The method of claim 32, wherein each carbohydrate is deposited at least in triplicate.

34. The method of claim 32, wherein the irradiation is accomplished using ultraviolet light.

35. The method of claim 32, wherein the irradiation is accomplished using light of a wavelength from 280 nm to 400 nm.

36. The method of claim 32, wherein the carbohydrate, monolayer, and optionally the surface are irradiated through a photomask.

37. The method of claim 32, wherein the compound of formula (I) is:

38. The method of claim 32, wherein the deposition is accomplished using a robotic spotter.

39. The method of claim 32, wherein at least one carbohydrate is selected from the group consisting of:

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-D-glucose,

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucose,

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-α

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1-43)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranoside;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

or

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose,

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1-2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tetrakis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyraposide]₅-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

a glycoside thereof; and

a combination thereof.

40. A method for making an array, the method comprising the steps of:

forming on at least a part of a surface a self-assembled monolayer, wherein the monolayer comprises a compound of Formula (I)

41. The method of claim 40, wherein the ratio of the compound of Formula (I) to the compound of Formula (III) is from about 1:

1 to about 1;

100.

42. The method of claim 40, wherein each carbohydrate is deposited at least in triplicate.

43. The method of claim 40, wherein the irradiation is accomplished using ultraviolet light.

44. The method of claim 40, wherein the irradiation is accomplished using light of a wavelength from 280 nm to 400 nm.

45. The method of claim 40, wherein the carbohydrate, monolayer, and optionally the surface are irradiated through a photomask.

46. The method of claim 40, wherein the compound of Formula (I) is:

47. The method of claim 40, wherein the compound of Formula (III) is

48. The method of claim 40, wherein the deposition is accomplished using a robotic spotter.

49. The method of claim 40, wherein at least one carbohydrate is selected from the group consisting of:

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-α

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranose,

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose,

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose,

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)—

β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranoside;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1-43)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

or

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tetrakis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₅-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

a glycoside thereof; and

a combination thereof.

50. The method of claim 40, wherein Y is —

NH₂.

51. A method for detecting a molecule that inhibits an agent-carbohydrate interaction, the method comprising the steps of:

depositing an agent onto a carbohydrate on an array;

washing the structure to substantially remove any unbound agent;

incubating the bound agent with a molecule, wherein the molecule is capable of binding to the agent and displacing the first carbohydrate;

incubating the array with an anti-agent antibody;

washing the structure to substantially remove any unbound anti-agent antibody;

treating the array with a labeled secondary antibody;

reading the array with a label reader to determine an amount of bound labeled secondary antibody, wherein a non-zero amount of bound labeled secondary antibody indicates that the molecule inhibits agent-carbohydrate interactions; and

wherein the array comprises;

a surface;

a compound of formula (I);

52. The method of claim 51, wherein the agent is an antibody.

53. The method of claim 51, wherein the antibody specifically binds Bacillus anthracis.

54. The method of claim 51, wherein the carbohydrate is selected from the group consisting of:

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucose,

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-α

-D-glucose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1->

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-rhamnopyranose;

α

-L-rhamnopyranosyl-(1->

3)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-β

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1-42)-α

-L-rhamnopyranose;

2-O-methyl-4-(3-hydroxy-3-methylbutamido)-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1-43)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranoside;

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-α

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranoside;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-D-glucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranose;

L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose;

or

n-Pentenyl 4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β

-Dglucopyranosyl-(1→

3)-β

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-α

-L-rhamnopyranose,

5-(Methoxycarbonyl)-pentyl-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-4,6-dideoxy-β

-D-glucopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

3)-α

-L-rhamnopyranosyl-(1→

2)-β

-L-rhamnopyranose;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tetrakis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₅-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-bis[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

[Methyl 2-O-methyl-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)-tris[4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranosyl-(1→

2)]-4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-D-mannopyranoside]₁₀-BSA;

a glycoside thereof; and

a combination thereof.

55. The method of claim 51, wherein the labeled secondary antibody is a fluorescent-labeled secondary antibody and the label reader is a fluorescent reader.