Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyI)cyclopent-2-en-r-l-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase

Nobuya Katagiri, Takuya Shiraishi, Akemi Toyota, Hiroshi Sato, Chikara Kaneko, Toyoo Aikawa

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-l-yl]-9H-adenine (BCA) by adenosine deaminase under a variety of pressures (1 bar—6 kbar) was investigated. It was found that, while (+)-BCA was practically unaffected, the deamination of (-)-BCA was remarkably enhanced under 4 kbar to give the corresponding (-)-hypoxanthine derivative [(-)-BCH)] in nearly 100% ee.

Original languageEnglish
Pages (from-to)1027-1029
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number6
DOIs
Publication statusPublished - 1993

Keywords

  • 9-cyclopentenylhypoxanthine
  • adenosine deaminase
  • anti-HIV activity
  • carbocyclic adenine nucleoside
  • enzymatic resolution
  • high-pressure

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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