Synthesis of Regioselectively Protected Forms of Cytidine Based on Enzyme-catalyzed Deacetylation as the Key Step

Atsuhito KUBOKI; Takashi ISHIHARA; Eiko KOBAYASHI; Hiromichi OHTA; Takeshi ISHII; Ayumu INOUE; Satoshi MITSUDA; Tatsuo MIYAZAKI; Yasuhiro KAJIHARA; Takeshi SUGAI

doi:10.1271/bbb.64.363

Organic Chemistry Regular Papers

Synthesis of Regioselectively Protected Forms of Cytidine Based on Enzyme-catalyzed Deacetylation as the Key Step

Atsuhito KUBOKI, Takashi ISHIHARA, Eiko KOBAYASHI, Hiromichi OHTA, Takeshi ISHII, Ayumu INOUE, Satoshi MITSUDA, Tatsuo MIYAZAKI, Yasuhiro KAJIHARA, Takeshi SUGAI

Author information

Atsuhito KUBOKI
Department of Chemistry, Keio University
Takashi ISHIHARA
Department of Chemistry, Keio University
Eiko KOBAYASHI
Department of Chemistry, Keio University
Hiromichi OHTA
Department of Chemistry, Keio University
Takeshi ISHII
Biotechnology Laboratory, Sumitomo Chemical Co. Ltd.
Ayumu INOUE
Biotechnology Laboratory, Sumitomo Chemical Co. Ltd.
Satoshi MITSUDA
Biotechnology Laboratory, Sumitomo Chemical Co. Ltd.
Tatsuo MIYAZAKI
Department of System Function, Yokohama City University
Yasuhiro KAJIHARA
Department of System Function, Yokohama City University
Takeshi SUGAI
Department of Chemistry, Keio University

Keywords: cytidine, esterase, lipase, selective deacetylation, phosphorylation

JOURNAL FREE ACCESS

2000 Volume 64 Issue 2 Pages 363-368

DOI https://doi.org/10.1271/bbb.64.363

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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.

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