Silatranyl-nucleosides: transition state analogues for phosphoryl transfer reactions

A novel class of compounds that contain a silatrane moiety attached to or incorporated within a nucleoside is described. These compounds are transition state analogues for phosphoryl transfer reactions and as such have potential antiviral and anticancer properties. The two-step synthesis of 3 '...

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Published inTetrahedron letters Vol. 42; no. 30; pp. 4979 - 4982
Main Authors Sculimbrene, BR, Decanio, RE, Peterson, BW, Muntel, EE, Fenlon, EE
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 23.07.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
CATALYSIS
RIBONUCLEASE
COMPLEXES
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Summary:A novel class of compounds that contain a silatrane moiety attached to or incorporated within a nucleoside is described. These compounds are transition state analogues for phosphoryl transfer reactions and as such have potential antiviral and anticancer properties. The two-step synthesis of 3 ' -O-(trimethyl)silatranylthymidine (1) in 17% yield is reported. The aqueous half-life of 1 was determined to be 62 h by H-1 NMR. The syntheses of three 2 ' ,3 ' -protected-5 ' -O-silatranyladenosine in 25-55% yields are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)00942-X