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

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

5 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 language	English
Pages (from-to)	363-368
Number of pages	6
Journal	Bioscience, Biotechnology and Biochemistry
Volume	64
Issue number	2
DOIs	https://doi.org/10.1271/bbb.64.363
Publication status	Published - 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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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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T1 - Synthesis of Regioselectively Protected Forms of Cytidine Based on Enzyme-catalyzed Deacetylation as the Key Step

AU - Kuboki, Atsuhito

AU - Ishihara, Takashi

AU - Kobayashi, Eiko

AU - Ohta, Hiromichi

AU - Ishii, Takeshi

AU - Inoue, Ayumu

AU - Mitsuda, Satoshi

AU - Miyazaki, Tatsuo

AU - Kajihara, Yasuhiro

AU - Sugai, Takeshi

PY - 2000/1/1

Y1 - 2000/1/1

N2 - 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.

AB - 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.

KW - Cytidine

KW - Esterase

KW - Lipase

KW - Phosphorylation

KW - Selective deacetylation

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

Abstract

Keywords

ASJC Scopus subject areas

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