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US 5,151,507 AGranted
Alkynylamino-nucleotides
AssigneeE. I. Du Pont de Nemours and Company
InventorsFrank W. Hobbs, Jr., George L. Trainor
Life of this patent
Estimating the term…
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.
Claims9
An alkynylamino-nucleotide having the structure:
- Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3
- wherein
- R.sub.1 is --CH.sub.2 OCH.sub.2 (CH.sub.2 OCH.sub.2).sub.n CH.sub.2 -- and n=2-5
- R.sub.2 and R.sub.3 are, independently, H, C.sub.1 -C.sub.4 alkyl or a protecting group, and
- Nuc is R.sub.4 -Het having the structure ##STR18## Z is H or NH.sub.2, and R.sub.4 is ##STR19## wherein R.sub.5 is H, PO.sub.3 H.sub.2, P.sub.2 O.sub.6 H.sub.3, P.sub.3 O.sub.9 H.sub.4 or salts thereof, and
- (i) when R.sub.7 =R.sub.8 =H, then R.sub.6 =H, OH, F, N.sub.3 or NH.sub.2 ;
- or
- (ii) when R.sub.7 =H and R.sub.8 =OH, then R.sub.6 =H or OH;
- or
- (iii) when R.sub.7 =OH and R.sub.8 =H, then R.sub.6 =OH.
7 more elements
A labeled alkynylamino-nucleotide having the structure:
- Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3
- wherein
- R.sub.1 is --CH.sub.2 OCH.sub.2 (CH.sub.2 OCH.sub.2).sub.n CH.sub.2 -- and n=2-5,
- R.sub.2 is H, C.sub.1 -C4 alkyl or a protecting group, and
- Nuc is R.sub.4 -Het having the structure ##STR20## Z is H or NH.sub.2, and R.sub.4 is ##STR21## wherein R.sub.5 is H, PO.sub.3 H.sub.2, P.sub.2 O.sub.6 H.sub.3, P.sub.3 O.sub.9 H.sub.4 or salts thereof, and
- (i) when R.sub.7 =R.sub.8 =H, then R.sub.6 =H, OH, F, N.sub.3 or NH.sub.2 ;
- or
- (ii) when R.sub.7 =H and R.sub.8 =OH, then R.sub.6 =H or OH;
- or
- (iii) when R.sub.7 =OH and R.sub.8 =H, then R.sub.6 =OH and
- R.sub.3 is a reporter group.
8 more elements
An alkynylamino-nucleotide having the structure:
- Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3
- wherein
- R.sub.1 is a diradical moiety of 1-20 atoms,
- R.sub.2 is H, C.sub.1 -C.sub.4 alkyl or a protecting group,
- R.sub.3 contains a biotin moiety, and
- Nuc is R.sub.4 -Het having the structure ##STR22## Z is H or NH.sub.2, and R.sub.4 is ##STR23## wherein R.sub.5 is H, PO.sub.3 H.sub.2, P.sub.2 O.sub.6 H.sub.3, P.sub.3 O.sub.9 H.sub.4 or salts thereof, and
- (i) when R.sub.7 =R.sub.8 =H, then R.sub.6 =H, OH, F, N.sub.3 or NH.sub.2 ;
- or
- (ii) when R.sub.7 =H and R.sub.8 =OH, then R.sub.6 =H or OH;
- or
- (iii) when R.sub.7 =OH and R.sub.8 =H, then R.sub.6 =OH.
8 more elements
An alkynylamino-nucleotide having the structure:
- Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3
- wherein R.sub.1 is --CH.sub.2 OCH.sub.2 (CH.sub.2 OCH.sub.2).sub.n CH.sub.2 -- and n=2-5
- R.sub.2 and R.sub.3 are, independently, H, C.sub.1 -C.sub.4 alkyl or a protecting group, and
- Nuc is R.sub.4 -Het having the structure ##STR24## Z is H or NH.sub.2, and R.sub.4 is ##STR25## wherein R.sub.5 is H, PO.sub.3 H.sub.2, P.sub.2 O.sub.6 H.sub.3, P.sub.3 O.sub.9 H.sub.4 or salts thereof, and
- (i) when R.sub.7 =R.sub.8 =H, then R.sub.6 =H, OH, F, N.sub.3 or NH.sub.2 ;
- or
- (ii) when R.sub.7 =H and R.sub.8 =OH, then R.sub.6 =H or OH;
- or
- (iii) when R.sub.7 =OH and R.sub.8 =H, then R.sub.6 =OH, and
- R.sub.3 is a reporter group comprising biotin.
7 more elements
Dependencies are inferred from the claim text.