6-THIO-2'-DEOXYINOSINE - SYNTHESIS, INCORPORATION, AND EVALUATION AS A POSTSYNTHETICALLY MODIFIABLE BASE IN OLIGONUCLEOTIDES

Authors
COLEMAN RS ARTHUR JC MCCARY JL
Citation
Rs. Coleman et al., 6-THIO-2'-DEOXYINOSINE - SYNTHESIS, INCORPORATION, AND EVALUATION AS A POSTSYNTHETICALLY MODIFIABLE BASE IN OLIGONUCLEOTIDES, Tetrahedron, 53(32), 1997, pp. 11191-11202
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
32
Year of publication
1997
Pages
11191 - 11202
Database
ISI
SICI code
0040-4020(1997)53:32<11191:6-SIAE>2.0.ZU;2-S
Abstract
The synthesis of 6-thio-2'-deoxyinosine (d(S6)I) in a form suitably pr otected for solid-phase oligonucleotide synthesis is reported. This th ionucleic acid was incorporated in high yield into short oligodeoxynuc leotides, and the thiocarbonyl group could be modified by S-alkylation with complete chemoselectivity. The quantitation of incorporation and facile post-synthetic modification was demonstrated by enzymatic dige stion and HPLC analysis, and the effect of covalent alkylation was det ermined by Delta T-m measurements of the corresponding duplex oligonuc leotides with dC as the complementary base. (C) 1997 Elsevier Science Ltd.