Modified Amino Acids

• US 20170267637A1
• Filed: 05/24/2017
• Published: 09/21/2017
• Est. Priority Date: 08/31/2012
• Status: Active Grant

• Current Assignee: Sutro Biopharma, Inc.
• Original Assignee: Sutro Biopharma, Inc.
• Inventors: STAFFORD, Ryan, THANOS, Christopher D., YANG, Wenjin
• Granted Patent: US 9,994,527 B2
• Time in Patent Office: Days
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: C07C 247/04 being saturated
• CPC Class Codes: C07C 271/20 to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 275/14 being further substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07D 213/55 Acids; Esters
• CPC Class Codes: C07K 14/00 Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
• CPC Class Codes: C07K 14/535 Granulocyte CSF; Granulocyte-macrophage CSF
• CPC Class Codes: C07K 16/00 Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies antibodies with enzymatic activity, e.g. abzymes C12N9/0002

Abstract

Provided herein are modified amino acids comprising an azido group, polypeptides, antibodies and conjugates comprising the modified amino acids, and methods of producing the polypeptides, antibodies and conjugates comprising the modified amino acids. The polypeptides, antibodies and conjugates are useful in methods of treatment and prevention, methods of detection and methods of diagnosis.

Claims

1-14. -14. (canceled)

15. A polypeptide which is a polymer of amino acid residues where one or more amino acid residues is according to the following formula IIc:

16-22. -22. (canceled)

23. A polypeptide which is a polymer of amino acid residues where one or more amino acid residues is according to the following formula:

25. A conjugate prepared by contacting an alkyne-containing payload with a polypeptide which is a polymer of amino acid residues where one or more amino acid residues is according to formula IIa:

26. The conjugate of claim 25, wherein the one or more amino acid residues of formula IIa is according to formula 30:

27. The conjugate of claim 25, wherein the amino acid residue according to formula IIa and the alkyne-containing payload are linked via a linking moiety comprising a triazole.

28. The conjugate of claim 25, wherein the amino acid residue according to formula IIa and the alkyne-containing payload are linked via a linking moiety comprising a polyethylene glycol.

29. The conjugate of claim 25, wherein the alkyne-containing payload comprises DBCO.

30. A method for producing a conjugate, comprising:

a) reacting a molecule comprising a carbohydrate with a reagent to generate an alkyne-containing carbohydrate; and

b) forming the conjugate by combining the alkyne-containing carbohydrate with a polypeptide which is a polymer of amino acid residues where one or more amino acid residues is according to formula IIa;

31. The method of claim 30, comprising reacting the carbohydrate with periodate.

32. The method of claim 30, wherein the reagent comprises DBCO.

33. The method of claim 30, wherein the one or more amino acid residues of formula IIa is according to formula 30: