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Stereospecific synthesis of phosphotriesters by using new condensing reagents

Research Project

Project/Area Number 59570894
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHokkaido University (1985-1986)
Osaka University (1984)

Principal Investigator

OHTSUKA Eiko  Hokkaido University Fac.of Pharmaceutical Sciences, Prof, 薬学部, 教授 (80028836)

Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1986: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1985: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1984: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsPhosphotriester method / condensing reagent / Oligonucleotide / シアステレオマー
Research Abstract

Deoxyadenylyl-(3'-5')-phosphoro-o-chlorophenyl deoxyadenosine having the Sp configuration was synthesized stereoselectively by condensing N,5'-bis-dimethoxytrityldeoxyadenosine 3'-(o-chlorophenyl)phosphate with N,3'-bis-dimethoxytrityldeoxyadenosine using 1-2,4,6-triisopropylbenzene-5-(pyridin-2-yl)tetrazole as the condensing reagent followed by dedimethoxytritylation. The absolute configuration of this diastereomer was determined spectroscopically by comparison of two corresponding diastereomers which were prepared by using a conventional condensing reagent and isolated by chromatography on silica gel. Their nuclear Overhauser effect in proton magnetic resonances and the circular dichroism of these two diastereoisomers could only be explained if the product obtained by the stereoselective synthesis of this type exist in solution as an equilibrium of folded and extended forms.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Eiko Ohtsuka, Zenzaburo Tozuka and Morio Ikehara: "New condensing reagents for stereospecific synthesis of dinucleoside monophosphate aryl esters" Tetrahedron Letters. 22 (45). 4483-4486 (1981)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Eiko Ohtsuka, Zenzaburo Tozuka, Shigenori Iwai and Morio Ikehara: "A new condensing reagent, 1-(2,4,6-triisopropylbenzenesulfonyl)-5-(pyridin-2-yl) tetrazolide and its use in the synthesis of cro binding heptadecanucleotide on a polymer support" Nucleic Acids Research. 10 (20). 6235-6241 (1982)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Eiko Ohtsuka, Masahiko Shiraishi and Morio Ikehara: "Stereospecific synthesis of dinucleoside monophosphate aryl esters by using new condensing reagents" Phosphorus and Sulfer. 18. 365-368 (1983)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Eiko Ohtsuka, Masahiko Shiraishi and Morio Ikehara: "Stereoselective synthesis of dinucleoside phosphate aryl esters by using new condensing reagents, arenesulfonyl 5-(pyridin-2-yl)-tetrazole" Tetrahedron. 41 (22). 5271-5277 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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