Synthesis of regioselectively protected forms of cytidine based on enzyme-catalyzed deacetylation as the key step

A Kuboki; T Ishihara; E Kobayashi; H Ohta; T Ishii; A Inoue; S Mitsuda; T Miyazaki; Y Kajihara; T Sugai

doi:10.1271/bbb.64.363

Synthesis of regioselectively protected forms of cytidine based on enzyme-catalyzed deacetylation as the key step

Biosci Biotechnol Biochem. 2000 Feb;64(2):363-8. doi: 10.1271/bbb.64.363.

Authors

A Kuboki¹, T Ishihara, E Kobayashi, H Ohta, T Ishii, A Inoue, S Mitsuda, T Miyazaki, Y Kajihara, T Sugai

Affiliation

¹ Department of Chemistry, Keio University, Yokohama, Japan.

PMID: 10737194
DOI: 10.1271/bbb.64.363

Abstract

N4-Acetylcytidine (77%) and 2',3'-O, N4-triacetylcytidine (95%) were obtained from the hydrolysis of a common precursor, the peracetylated form of cytidine with Aspergillus niger lipase (Amano A) and Burkholderia cepacia esterase (SC esterase S), respectively, under very mild conditions. The experimental procedure for the conversion of triacetylcytidine to a corresponding phosphoramidite (82%), an intermediate for sugar nucleotide synthesis, is also elaborated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylation
Aspergillus niger / enzymology
Burkholderia cepacia / enzymology
Catalysis
Cytidine / chemical synthesis*
Cytidine / chemistry
Esterases / metabolism*
Hydrolysis
Lipase / metabolism*
Spectrum Analysis

Substances

Cytidine
Esterases
Lipase