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

• Published in: Bioscience, biotechnology, and biochemistry Vol. 64; no. 2; pp. 363 - 368
• Main Authors: KUBOKI, Atsuhito, ISHIHARA, Takashi, KOBAYASHI, Eiko, OHTA, Hiromichi, ISHII, Takeshi, INOUE, Ayumu, MITSUDA, Satoshi, MIYAZAKI, Tatsuo, KAJIHARA, Yasuhiro, SUGAI, Takeshi
• Format: Journal Article
• Language: English
• Published: ABINGDON Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.01.2000; Taylor & Francis; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: Acetylation; Aspergillus niger - enzymology; Biochemistry & Molecular Biology; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Biotechnology & Applied Microbiology; Burkholderia cepacia - enzymology; Catalysis; Chemistry; Chemistry, Applied; cytidine; Cytidine - chemical synthesis; Cytidine - chemistry; esterase; Esterases - metabolism; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Hydrolysis; Life Sciences & Biomedicine; lipase; Lipase - metabolism; Methods. Procedures. Technologies; phosphorylation; Physical Sciences; Science & Technology; selective deacetylation; Spectrum Analysis; 2',3'-DIDEOXYCYTIDINE; ACID; ENANTIOSELECTIVITY; NUCLEOSIDES; lipase; RESOLUTION; cytidine; selective deacetylation; TEMPERATURE; ENHANCEMENT; ESTERS; esterase; phosphorylation; Enzymatic synthesis; Protecting group; Phosphorylation; Regioselectivity; Enzyme; Triacylglycerol lipase; Enzymatic catalysis; Esterases; Cytidine; Carboxylic ester hydrolases; Fungi; Aspergillus niger; Deacetylation; Burkholderia cepacia; Bacteria; Hydrolases; Fungi Imperfecti; Pyrimidine nucleoside; Thallophyta
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.64.363

N 4 -Acetylcytidine (77%) and 2′,3′-O,N 4 -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.