Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase

Abstract

Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-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.