US5151507A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkynylamino-nucleotides
Assignee: Revvity Health Sciences Inc
•
Filing: 1991-06-12
•
Granted: 1992-09-29
•
Expires: 2011-06-12
Abstract
Abstract Alkynylamino-nucleotides and labeled alkynylaminonucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation. For some applications, longer, hydrophilic linkers are provided.
Inventors
- 👤 Frank W. Hobbs, Jr.
- 👤 George L. Trainor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 12:11
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D405/12; C07D405/14; C07D471/00; C07D471/02; C07D471/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/6512; C07F9/6558; C07F9/65586; C07F9/6561; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6869; G; G01; G01N; G01N27/00; G01N27/26; G01N27/416; G01N27/447; G01N27/44704; G01N27/44717; G01N27/44721; G01N27/44726
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
142 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5 R 2 and R 3 are, independently, H, C 1 -C 4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR18## Z is H or NH 2 , and R 4 is ##STR19## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH.
Claim 2
Dependent Claim
142 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5 R 2 and R 3 are, independently, H, C 1 -C 4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR18## Z is H or NH 2 , and R 4 is ##STR19## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH.
Claim 3
Dependent Claim
7 words
The alkynylamino-nucleotide of claim 1 wherein n=2.
Claim 4
Dependent Claim
19 words
The alkynylamino-nucleotide of claim 1 wherein R 2 is H and R 3 is H or a protecting group.
Claim 5
Dependent Claim
145 words
A labeled alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5, R 2 is H, C 1 -C4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR20## Z is H or NH 2 , and R 4 is ##STR21## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH and R 3 is a reporter group.
Claim 6
Dependent Claim
145 words
A labeled alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5, R 2 is H, C 1 -C4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR20## Z is H or NH 2 , and R 4 is ##STR21## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH and R 3 is a reporter group.
Claim 7
Dependent Claim
13 words
The labeled alkynylamino-nucleotide of claim 4 wherein R 3 is a fluorescent group.
Claim 8
Dependent Claim
8 words
The labeled alkynylamino-nucleotide of claim 4 wherein n=2.
Claim 9
Dependent Claim
135 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is a diradical moiety of 1-20 atoms, R 2 is H, C 1 -C 4 alkyl or a protecting group, R 3 contains a biotin moiety, and Nuc is R 4 -Het having the structure ##STR22## Z is H or NH 2 , and R 4 is ##STR23## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH.
Claim 10
Dependent Claim
135 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is a diradical moiety of 1-20 atoms, R 2 is H, C 1 -C 4 alkyl or a protecting group, R 3 contains a biotin moiety, and Nuc is R 4 -Het having the structure ##STR22## Z is H or NH 2 , and R 4 is ##STR23## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH.
Claim 11
Dependent Claim
12 words
The alkynylamino-nucleotide of claim 7 wherein R 1 is --CH 2 --.
Claim 12
Dependent Claim
151 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5 R 2 and R 3 are, independently, H, C 1 -C 4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR24## Z is H or NH 2 , and R 4 is ##STR25## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH, and R 3 is a reporter group comprising biotin.
Claim 13
Dependent Claim
151 words
An alkynylamino-nucleotide having the structure: Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3 wherein R 1 is --CH 2 OCH 2 (CH 2 OCH 2 ) n CH 2 -- and n=2-5 R 2 and R 3 are, independently, H, C 1 -C 4 alkyl or a protecting group, and Nuc is R 4 -Het having the structure ##STR24## Z is H or NH 2 , and R 4 is ##STR25## wherein R 5 is H, PO 3 H 2 , P 2 O 6 H 3 , P 3 O 9 H 4 or salts thereof, and (i) when R 7 =R 8 =H, then R 6 =H, OH, F, N 3 or NH 2 ; or (ii) when R 7 =H and R 8 =OH, then R 6 =H or OH; or (iii) when R 7 =OH and R 8 =H, then R 6 =OH, and R 3 is a reporter group comprising biotin.
References Cited (Backward Citations)
US5047519A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-09-29 | 1996-03-30 | 1996-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-09-29 | 2000-03-30 | 2000-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-09-29 | 2004-03-30 | 2004-09-29 | $7700.00 | Window Closed / Lapsed |