Modified nucleotides and methods of preparing and using same
DC CAFCFirst Claim
1. A nucleotide or oligo- or polynucleotide sequence comprising at least one of a moiety having the structure:
- wherein B represents a 7-deazapurine or a pyrimidine moiety;
wherein A represents a moiety selected from the group consisting of biotin and iminobiotin;
provided that if B is a 7-deazapurine, A is attached to the 7-position of the deazapurine, and if B is a pyrimidine, A is attached to the 5-position of the pyrimidine, A being attached to B directly or through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavidin or antibodies to biotin or iminobiotin.
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Abstract
Compounds having the structure: ##STR1## wherein B represents a purine, 7-deazapurine, or pyrimidine moiety covalently bonded to the C1'"'"' -position of the sugar moiety, provided that when B is purine or 7-deazapurine, it is attached at the N9 -position of the purine or 7-deazapurine and when B is pyrimidine, it is attached at the N1 -position;
wherein A represents a moiety consisting of at least three carbon atoms which is capable of forming a detectable complex with a polypeptide when the compound is incorporated into a double-stranded ribonucleic acid, deoxyribonucleic acid duplex, or DNA-RNA hybrid;
wherein the dotted line represents a chemical linkage joining B and A, provided that if B is purine, the linkage is attached to the 8-position of the purine, if B is 7-deazapurine, the linkage is attached to the 7-position of the deazapurine, and if B is pyrimidine, the linkage is attached to the 5-position of the pyrimidine and
wherein each of x, y and z represents ##STR2## either directly, or when incorporated into oligo- and polynucleotides, provide probes which are widely useful.
Applications include detection and localization of polynucleotide sequences in chromosomes, fixed cells, tissue sections, and cell extracts. Specific applications include chromosomal karyotyping, clinical diagnosis of nucleic acid-containing etiological agents, e.g. bacteria, viruses, or fungi, and diagnosis of genetic disorders.
896 Citations
22 Claims
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1. A nucleotide or oligo- or polynucleotide sequence comprising at least one of a moiety having the structure:
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wherein B represents a 7-deazapurine or a pyrimidine moiety; wherein A represents a moiety selected from the group consisting of biotin and iminobiotin; provided that if B is a 7-deazapurine, A is attached to the 7-position of the deazapurine, and if B is a pyrimidine, A is attached to the 5-position of the pyrimidine, A being attached to B directly or through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavidin or antibodies to biotin or iminobiotin. - View Dependent Claims (2, 3, 4)
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5. A compound having the structure:
- ##STR26## wherein B represents a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1'"'"' -position of the sugar moiety, provided that when B is a 7-deazapurine, it is attached at the N9 -position of the deazapurine, and when B is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
wherein A represents a moiety selected from the group consisting of biotin and iminobiotin; provided that if B is a 7-deazapurine, A is attached to the 7-position of the deazapurine, and if B is a pyrimidine, A is attached to the 5-position of the pyrimidine, A being attached to B directly or through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavidin or antibodies to biotin or iminobiotin; wherein X represents a moiety selected from the group consisting of;
##STR27## wherein Y is --OH and Z is --OH or --H. - View Dependent Claims (6, 7, 8)
- ##STR26## wherein B represents a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1'"'"' -position of the sugar moiety, provided that when B is a 7-deazapurine, it is attached at the N9 -position of the deazapurine, and when B is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
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9. A poly- or oligonucleotide sequence which comprises at least one of a moiety having the structure:
- ##STR29## wherein B represents a purine, a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1'"'"' -position of the sugar moiety, provided that when B is a purine or a 7-deazapurine, it is attached at the N9 -position of the purine or deazapurine, and when B is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
wherein A represents a moiety selected from the group consisting of biotin and iminobiotin; provided that if B is a purine, A is attached to the 8-position of the purine, if B is a 7-deazapurine, A is attached to the 7-position of the deazapurine, and if B is a pyrimidine, A is attached to the 5-position of the pyrimidine, A being attached to B directly or through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavidin or antibodies to biotin or iminobiotin; and
wherein Z represents;
##STR30## - View Dependent Claims (10, 11, 12, 13, 14)
- ##STR29## wherein B represents a purine, a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1'"'"' -position of the sugar moiety, provided that when B is a purine or a 7-deazapurine, it is attached at the N9 -position of the purine or deazapurine, and when B is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
- 15. A double-stranded RNA or DNA duplex or DNA-RNA hybrid which comprises:
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16. (i) in one strand a poly- or oligonucleotide sequence which comprises at least one of a moiety having the structure:
- ##STR32## wherein B represents a purine, a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1 -position of the sugar moiety provided that when B is a purine or a 7-deazapurine, it is attached at the N9 -position of the purine or deaazapurine, and when b is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
wherein A represents a moiety selected from the group consisting of biotin and iminobiotin; provided that if B is a purine, A is attached to the 8-position of the purine, if B is a 7-deazapurine, A is attached to the 7-position of the deazapurine, and if B is a pyrimidine, A is attached to the 5-position of the pyrimidine, A being attached to B directly or through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavidin or antibodies to biotin or iminobiotin; and wherein Z represents ##STR33## and (ii) in the second strand, a poly- or oligonucleotide sequence containing neither a biotin nor iminobiotin.
- ##STR32## wherein B represents a purine, a 7-deazapurine or a pyrimidine moiety covalently bonded to the C1 -position of the sugar moiety provided that when B is a purine or a 7-deazapurine, it is attached at the N9 -position of the purine or deaazapurine, and when b is a pyrimidine, it is attached at the N1 -position of the pyrimidine;
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22. A nucleotide or oligo- or polynucleotide sequence comprising at least one of a moiety having the structure:
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space="preserve" listing-type="equation">--BAwherein B represents a purine; wherein A represents a moiety selected from the group consisting of biotin and iminobiotin, attached to the 8-position of the purine, A being attached to B through a linkage group, said linkage group not interfering substantially with the characteristic ability of A to form a detectable complex with one of avidin, streptavadin or antibodies to biotin or iminobiotin, and being characterized by an olefinic bond at the α
-position relative to B.
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Specification