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Paper | Regular issue | Vol 27, No. 12, 1988, pp.2891-2901
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4757
Synthesis and Structure of a Fluorescent, Tricyclic Analogue of 2’-Deoxyadenosine and of a Prodrug by N-Annelation of 2’-Deoxyguanosine and 9-[(2-Hydroxyethoxy)methyl]guanine (Acyclovir), Respectively

Shiv Kumar, Fred T. Oakes, Scott R. Wilson, and Nelson J. Leonard*

*Roger Adams Laboratory, School of Chemical Sciences, University of Illinois, 1209 West California Street, Urbana, IL 61801-3731, U.S.A.

Abstract

Chemical modification of 2’-deoxyguanosine and of 9-[(2-hydroxyethoxy)-methyl]guanine, respectively, into a fluorescent, tricyclic analogue of deoxyadenosine with potential for use as a probe for enzymatic reactions, and into a prodrug of an effective antiherpetic, acyclovir, is described. The X-ray structure determination of 8-amino-3,10-dihydro-10-oxo-3-(β-D-2-deoxyribofuranosyl)-3H-1,3,5-triazino[1,2-a] purine (dIdA’-metamorphosine) revealed that the nucleoside is in syn conformation, x = 55.1°, with an intramolecular hydrogen bond 0(5’)-H(5’)---N(4)= 2.810Å. The 2’-deoxyribofuranosyl ring is in a 2’-endo envelope (2E) conformation, and the conformation about the C(4’)-C(5’) bond is gauche-gauche.