Alkynylamino-nucleotides
First Claim
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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.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.
248 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
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Current AssigneePerkinElmer Life Sciences, Inc.
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Original AssigneeE. I. du Pont de Nemours and Company (Corteva, Inc.)
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InventorsTrainor, George L., Hobbs, Frank W. Jr.
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Primary Examiner(s)Brown, Johnnie R.
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Assistant Examiner(s)WILSON, JAMES O
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Application NumberUS07/713,906Time in Patent Office475 DaysField of Search536/23, 536/24, 536/26, 536/27, 536/29, 544/243, 544/244US Class Current536/26.7CPC Class CodesC07D 405/04 directly linked by a ring-m...C07D 405/12 linked by a chain containin...C07D 405/14 containing three or more he...C07D 471/04 Ortho-condensed systemsC07F 9/6512 having the nitrogen atoms i...C07F 9/65586 at least one of the hetero ...C07F 9/6561 containing systems of two o...C07H 19/06 Pyrimidine radicalsC07H 19/10 with the saccharide radical...C07H 19/20 with the saccharide radical...C07H 21/00 Compounds containing two or...C12Q 1/6869 Methods for sequencingG01N 27/44721 by optical meansG01N 27/44726 using specific dyes, marker...
