Remarkable acceleration for the deamination of carbocyclic purine nucleosides by adenosine deaminase under high-pressure.
Deamination of an anti-HIV carbocyclic adenine nucleoside, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(+/-)-BCA] and (+/-)-diamino-carbovir by adenosine deaminase under high-pressure (4 kbar) was carried out. Deamination of the former gave the corresponding (-)-hypoxanthine derivative whereas that of the latter produced (-)-carbovir having anti-HIV activity. The enantiomeric excess (e.e.) of both products was nearly 100%.
Katagiri
N
N
Pharmaceutical Institute, Tohoku University, Sendai, Japan.
Shiraishi
T
T
Toyota
A
A
Sato
H
H
Kaneko
C
C
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D000243:Adenosine Deaminase / Q000737:chemistry*; D000998:Antiviral Agents / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D003641:Deamination; D015224:Dideoxynucleosides / Q000737:chemistry; D006678:HIV; D011312:Pressure; D013237:Stereoisomerism
D000998:Antiviral Agents; D003517:Cyclopentanes; D015224:Dideoxynucleosides; C057503:carbovir; C074108:9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine; D000243:Adenosine Deaminase; D000225:Adenine