Enzymatic transesterification of purine nucleoside having a low solubility in organic medium.
Enzymatic transesterification of guanosine having low solubility against organic solvent was examined. For the transesterification between guanosine and divinyl adipate catalyzed by alkaline protease from Bacillus (Bioprase), DMSO was added to DMF to increase the solublility of the nucleoside, and the conversion rate of guanosine to the vinyl guanosine ester was less than 30%. To overcome the reversible inactivation of enzyme by hydrophilic organic solvents, the reaction was carried out with 10% (v/v) water. The transesterification reaction was effectively catalyzed in DMF/DMSO in the presence of water and the conversion rate increased ca. 70% after 7 d reaction. The result shows that the water effect of Bioprase would be a useful method for the synthesis of low solublility nucleoside esters.
Fan
Hong
H
National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan.
Kitagawa
Masaru
M
Raku
Takao
T
Tokiwa
Yutaka
Y
D000272:Adipates / Q000737:chemistry*; D001407:Bacillus / Q000201:enzymology*; D002384:Catalysis; D004789:Enzyme Activation; D004951:Esterification; D006151:Guanosine / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D011684:Purine Nucleosides / Q000737:chemistry; D012697:Serine Endopeptidases / Q000737:chemistry*; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D000272:Adipates; D009930:Organic Chemicals; D011684:Purine Nucleosides; D012997:Solvents; D014867:Water; D006151:Guanosine; C472390:divinyl adipate; D012697:Serine Endopeptidases; C032923:microbial serine proteinases