Alkynylamino-nucleotides
First Claim
Patent Images
1. An alkynylamino-nucleotide having the structure:
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space="preserve" listing-type="equation">Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3whereinR1 is --CH2 OCH2 (CH2 OCH2)n CH2 -- and n=2-5R2 and R3 are, independently, H, C1 -C4 alkyl or a protecting group, andNuc is R4 -Het having the structure ##STR18## Z is H or NH2, and R4 is ##STR19## wherein R5 is H, PO3 H2, P2 O6 H3, P3 O9 H4 or salts thereof, and(i) when R7 =R8 =H, then R6 =H, OH, F, N3 or NH2 ;
or(ii) when R7 =H and R8 =OH, then R6 =H or OH;
or(iii) when R7 =OH and R8 =H, then R6 =OH.
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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.
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Citations
9 Claims
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1. An alkynylamino-nucleotide having the structure:
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space="preserve" listing-type="equation">Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3wherein R1 is --CH2 OCH2 (CH2 OCH2)n CH2 -- and n=2-5 R2 and R3 are, independently, H, C1 -C4 alkyl or a protecting group, and Nuc is R4 -Het having the structure ##STR18## Z is H or NH2, and R4 is ##STR19## wherein R5 is H, PO3 H2, P2 O6 H3, P3 O9 H4 or salts thereof, and (i) when R7 =R8 =H, then R6 =H, OH, F, N3 or NH2 ;
or(ii) when R7 =H and R8 =OH, then R6 =H or OH;
or(iii) when R7 =OH and R8 =H, then R6 =OH. - View Dependent Claims (2, 3)
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4. A labeled alkynylamino-nucleotide having the structure:
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space="preserve" listing-type="equation">Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3wherein R1 is --CH2 OCH2 (CH2 OCH2)n CH2 -- and n=2-5, R2 is H, C1 -C4 alkyl or a protecting group, and Nuc is R4 -Het having the structure ##STR20## Z is H or NH2, and R4 is ##STR21## wherein R5 is H, PO3 H2, P2 O6 H3, P3 O9 H4 or salts thereof, and (i) when R7 =R8 =H, then R6 =H, OH, F, N3 or NH2 ;
or(ii) when R7 =H and R8 =OH, then R6 =H or OH;
or(iii) when R7 =OH and R8 =H, then R6 =OH and R3 is a reporter group. - View Dependent Claims (5, 6)
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7. An alkynylamino-nucleotide having the structure:
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space="preserve" listing-type="equation">Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3wherein R1 is a diradical moiety of 1-20 atoms, R2 is H, C1 -C4 alkyl or a protecting group, R3 contains a biotin moiety, and Nuc is R4 -Het having the structure ##STR22## Z is H or NH2, and R4 is ##STR23## wherein R5 is H, PO3 H2, P2 O6 H3, P3 O9 H4 or salts thereof, and (i) when R7 =R8 =H, then R6 =H, OH, F, N3 or NH2 ;
or(ii) when R7 =H and R8 =OH, then R6 =H or OH;
or(iii) when R7 =OH and R8 =H, then R6 =OH. - View Dependent Claims (8)
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9. An alkynylamino-nucleotide having the structure:
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space="preserve" listing-type="equation">Nuc--C.tbd.C--R.sub.1 --NR.sub.2 R.sub.3wherein R1 is --CH2 OCH2 (CH2 OCH2)n CH2 -- and n=2-5 R2 and R3 are, independently, H, C1 -C4 alkyl or a protecting group, and Nuc is R4 -Het having the structure ##STR24## Z is H or NH2, and R4 is ##STR25## wherein R5 is H, PO3 H2, P2 O6 H3, P3 O9 H4 or salts thereof, and (i) when R7 =R8 =H, then R6 =H, OH, F, N3 or NH2 ;
or(ii) when R7 =H and R8 =OH, then R6 =H or OH;
or(iii) when R7 =OH and R8 =H, then R6 =OH, and R3 is a reporter group comprising biotin.
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Specification