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
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.