US4711955A
Expired / Lapsed
US
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Modified nucleotides and methods of preparing and using same
Assignee: Yale University
•
Filing: 1983-05-23
•
Granted: 1987-12-08
•
Expires: 2003-05-23
Abstract
Abstract Compounds having the structure: ##STR1## wherein B represents a purine, 7-deazapurine, or pyrimidine moiety covalently bonded to the C 1' -position of the sugar moiety, provided that when B is purine or 7-deazapurine, it is attached at the N 9 -position of the purine or 7-deazapurine and when B is pyrimidine, it is attached at the N 1 -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.
Inventors
- 👤 David C. Ward
- 👤 Pennina R. Langer
- 👤 Alexander A. Waldrop, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 10:06
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16; C07H19/20; C07H21/00; C12; C12P; C12P19/00; C12P19/26; C12P19/28; C12P19/30; C12P19/34; C12Q; C12Q1/00; C12Q1/02; C12Q1/18; C12Q1/68; C12Q1/6804; C12Q1/6813; C12Q1/6816
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
110 words
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.
Claim 2
Dependent Claim
110 words
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.
Claim 3
Dependent Claim
16 words
The compound in accordance with claim 1, wherein B is a cytosine, uracil, deazaadenine or deazaguanine.
Claim 4
Dependent Claim
36 words
The nucleotide, or oligo- or polynucleotide sequence according to claim 1, wherein said linkage group is characterized by at least one of an olefinic bond at the α-position relative to B and a --CH 2 NH--.
Claim 5
Dependent Claim
26 words
The nucleotide or oligo- or polynucleotide sequence in accordance with claim 3, wherein the linkage group is characterized by the moiety --CH═CH--CH 2 --NH-- or ##STR25##
Claim 6
Dependent Claim
167 words
A compound having the structure: ##STR26## wherein B represents a 7-deazapurine or a pyrimidine moiety covalently bonded to the C 1' -position of the sugar moiety, provided that when B is a 7-deazapurine, it is attached at the N 9 -position of the deazapurine, and when B is a pyrimidine, it is attached at the N 1 -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.
Claim 7
Dependent Claim
167 words
A compound having the structure: ##STR26## wherein B represents a 7-deazapurine or a pyrimidine moiety covalently bonded to the C 1' -position of the sugar moiety, provided that when B is a 7-deazapurine, it is attached at the N 9 -position of the deazapurine, and when B is a pyrimidine, it is attached at the N 1 -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.
Claim 8
Dependent Claim
16 words
The compound in accordance with claim 5, wherein B is a uracil, cytosine, deazaadenine or deazaguanine.
Claim 9
Dependent Claim
32 words
The compound in accordance with claim 5, wherein said linkage group is characterized by at least one of an olefinic bond at the α-position relative to B and a --CH 2 --NH--.
Claim 10
Dependent Claim
27 words
The compound in accordance with claim 7, wherein the linkage group is characterized by a moiety selected from the group consisting of --CH═CH--CH 2 --NH-- and ##STR28##
Claim 11
Dependent Claim
182 words
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 C 1' -position of the sugar moiety, provided that when B is a purine or a 7-deazapurine, it is attached at the N 9 -position of the purine or deazapurine, and when B is a pyrimidine, it is attached at the N 1 -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##
Claim 12
Dependent Claim
182 words
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 C 1' -position of the sugar moiety, provided that when B is a purine or a 7-deazapurine, it is attached at the N 9 -position of the purine or deazapurine, and when B is a pyrimidine, it is attached at the N 1 -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##
Claim 13
Dependent Claim
13 words
The sequence in accordance with claim 9, wherein B is deazaadenine or deazaguanine.
Claim 14
Dependent Claim
32 words
The sequence in accordance with claim 9, wherein said linkage group is characterized by at least one of an olefinic bond at the α-position relative to B and a --CH 2 --NH--.
Claim 15
Dependent Claim
27 words
The sequence in accordance with claim 11, wherein the linkage group is characterized by a moiety selected from the group consisting of --CH═CH--CH 2 --NH-- and ##STR31##
Claim 16
Dependent Claim
13 words
The sequence in accordance with claim 9, wherein z is --OH or --H.
Claim 17
Dependent Claim
14 words
The sequence in accordance with claim 9, wherein B is a cytosine or uracil.
Claim 18
Dependent Claim
11 words
A double-stranded RNA or DNA duplex or DNA-RNA hybrid which comprises:
Claim 19
Dependent Claim
11 words
A double-stranded RNA or DNA duplex or DNA-RNA hybrid which comprises:
Claim 20
Dependent Claim
203 words
(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 C 1 -position of the sugar moiety provided that when B is a purine or a 7-deazapurine, it is attached at the N 9 -position of the purine or deaazapurine, and when b is a pyrimidine, it is attached at the N 1 -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.
Claim 21
Dependent Claim
203 words
(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 C 1 -position of the sugar moiety provided that when B is a purine or a 7-deazapurine, it is attached at the N 9 -position of the purine or deaazapurine, and when b is a pyrimidine, it is attached at the N 1 -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.
Claim 22
Dependent Claim
15 words
The duplex or hybrid in accordance with claim 15, wherein z is H-- or HO--.
Claim 23
Dependent Claim
17 words
The duplex or hybrid in accordance with claim 15, wherein B is a pyrimidine or a 7-deazapurine.
Claim 24
Dependent Claim
18 words
The duplex or hybrid in accordance with claim 17, wherein B is a uracil, cytosine, deazaadenine or deazaguanine.
Claim 25
Dependent Claim
34 words
The duplex or hybrid in accordance with claim 15, wherein said linkage group is characterized by at least one of an olefinic bond at the α-position relative to B and a --CH 2 --NH--.
Claim 26
Dependent Claim
29 words
The duplex or hybrid in accordance with claim 19, wherein the linkage group is characterized by a moiety selected from the group consisting of --CH═CH--CH 2 --NH-- and ##STR34##
Claim 27
Dependent Claim
94 words
A nucleotide or oligo- or polynucleotide sequence comprising at least one of a moiety having the structure: --BA wherein 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.
Claim 28
Dependent Claim
94 words
A nucleotide or oligo- or polynucleotide sequence comprising at least one of a moiety having the structure: --BA wherein 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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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-07 | 1991-06-08 | 1991-12-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-07 | 1995-06-08 | 1995-12-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-07 | 1999-06-08 | 1999-12-08 | $7700.00 | Window Closed / Lapsed |