Skip to main content
Journal cover image

A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates

Publication ,  Journal Article
Krzyzanowska, BK; He, K; Hasan, A; Shaw, BR
Published in: Tetrahedron
May 14, 1998

A new class of nucleotides, with one of the two non-bridging oxygens at α-phosphorus replaced by a borane (BH3) group, has shown potential applications in DNA sequencing. We have developed a convenient method for the synthesis of the 2'-deoxy-5'-(α-P-borano)triphosphates of adenosine, guanosine, cytidine, thymidine and uridine (6a-e) that is time and cost effective compared to the previously reported method. The appropriate base/sugar protected nucleoside 1 is phosphitylated with 2-chloro-4H-1,3,2- benzodioxaphosphorin-4-one to give the corresponding cyclic intermediate, 2- (2'-deoxyribonucleosidyl-5'-O-)-4H-1,3,2-benzodioxaphosphorin-4-one (2). The in situ reaction of 2 with pyrophosphate leads to P2,P3-dioxo-P1-(2'- deoxyribonucleosidyl-5')cyclotriphosphite (3). Subsequent reaction of 3 with N,N-diisopropylethylamine-borane complex yields P1-borano-(2'- deoxyribonucleosidyl-5')cyclotriphosphate (4), which upon hydrolysis under mild conditions gives the base/sugar protected 2'-deoxyribonucleoside-5'- (α-P-borano)triphosphate (5). Treatment of 5 with ammonia:methanol (2:1 v/v) yields the diastereoisomeric mixture of 2'-deoxyribonucleoside-5'-(α-P- borano)triphosphate (6). Separation of the two diastereoisomers of 6 is performed by reverse phase HPLC.

Duke Scholars

Altmetric Attention Stats
Dimensions Citation Stats

Published In

Tetrahedron

DOI

ISSN

0040-4020

Publication Date

May 14, 1998

Volume

54

Issue

20

Start / End Page

5119 / 5128

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Krzyzanowska, B. K., He, K., Hasan, A., & Shaw, B. R. (1998). A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates. Tetrahedron, 54(20), 5119–5128. https://doi.org/10.1016/S0040-4020(98)00251-8
Krzyzanowska, B. K., K. He, A. Hasan, and B. R. Shaw. “A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates.” Tetrahedron 54, no. 20 (May 14, 1998): 5119–28. https://doi.org/10.1016/S0040-4020(98)00251-8.
Krzyzanowska BK, He K, Hasan A, Shaw BR. A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates. Tetrahedron. 1998 May 14;54(20):5119–28.
Krzyzanowska, B. K., et al. “A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates.” Tetrahedron, vol. 54, no. 20, May 1998, pp. 5119–28. Scopus, doi:10.1016/S0040-4020(98)00251-8.
Krzyzanowska BK, He K, Hasan A, Shaw BR. A convenient synthesis of 2'-deoxyribonucleoside 5'-(α-P- borano)triphosphates. Tetrahedron. 1998 May 14;54(20):5119–5128.
Journal cover image

Published In

Tetrahedron

DOI

ISSN

0040-4020

Publication Date

May 14, 1998

Volume

54

Issue

20

Start / End Page

5119 / 5128

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry