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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)363-368
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume64
Issue number2
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • Cytidine
  • Esterase
  • Lipase
  • Phosphorylation
  • Selective deacetylation

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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    Kuboki, A., Ishihara, T., Kobayashi, E., Ohta, H., Ishii, T., Inoue, A., Mitsuda, S., Miyazaki, T., Kajihara, Y., & Sugai, T. (2000). Synthesis of Regioselectively Protected Forms of Cytidine Based on Enzyme-catalyzed Deacetylation as the Key Step. Bioscience, Biotechnology and Biochemistry, 64(2), 363-368. https://doi.org/10.1271/bbb.64.363