BORANE-AMINE COMPLEXES - VERSATILE REAGENTS IN THE CHEMISTRY OF NUCLEIC ACIDS AND THEIR ANALOGS

Abstract

A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4′-dimethoxytrityl (DMT) cation. Neutralization of the cation eliminated the boranophosphate group degradation during acidic DMT deprotection and allowed milder acidic conditions for the deprotection.

ACKNOWLEDGMENT

This work was supported by grants NIH 5R01-GM57693 and DOE DE-FG05-97ER62376 to B.R.S.