New neplanocin analogues. IX. A practical preparation of (6'R)-6'-C- methylneplanocin A (RMNPA), a potent antiviral agent, and the determination of its 6'-configuration. Diastereoselective deamination by adenosine deaminase

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 1, 1997, Pages 138-142

  Shuto, Satoshi ^a   Obara, Takumi ^b   Yaginuma, Satoshi ^b   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b ASAHI CHEMICAL INDUSTRY CO   (Japan)

Author keywords

adenosine deaminase; antiviral agent; modified Mosher's method; neplanocin A; S adenosylhomocysteine hydrolase

Indexed keywords

6' METHYLNEPLANOCIN A; NEPLANOCIN A; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DEAMINATION; DRUG EFFECT; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; METHYLATION; NONHUMAN;

EID: 0031013663     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.138     Document Type: Article

References (33)

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32. Although H-2 had a Δδ value of +0.001 ppm, the value was very small and may be an observational error. The small Δδ value of H-2 suggests that these MTPA esters would be in an anti-conformation around the glycosyl linkage, because Δδ values are proportional to the distance between the protons and the MTPA moiety (ref. 13).
33. When the enzymatic reaction was done at 35°C, considerable deamination of RMNPA was observed.