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Adenosine dialdehyde analogs I: Regioselective synthesis of adenosine monoaldehydes

โœ Scribed by John P. Neenan; Sumittada M. Opitz; Charles L. Cooke; Michael A. Ussery; Terence C. Morrill; Linda M. Eckel


Book ID
103983449
Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
284 KB
Volume
6
Category
Article
ISSN
0960-894X

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โœฆ Synopsis


Selective borohydride reduction of adenosine dialdehyde (1) gave the known adenosine 2'monoaldehyde (2). Reaction of I with N,N'-diphenylethylenediamine, followed by reduction and deblocking gave adenosine 3'-monoaldehyde ($), a new compound. Unlike 2, compound $ inhibited S-AdoHcy hydrolase and showed antiviral activity in vilro.


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pectively (e.g. for (2a) in CC14: v, , (CSj) = 1146vw, vs(CS2) = 61 9 cm-1 vs). Spectroscopic and X-ray data indicate pseudooctahedral environment of the metal in (/a)--( 2f) with (pseudo)-Czv symmetry. The IH-NMR spectra indicate in particular that an isomeric mixture containing (Ze) and a tolyldit