Controllable regioselective enzymatic synthesis of polymerizable 5'-O-vinyl- and 3'-O-vinyl-nucleoside analogues in acetone.
An efficient synthesis of polymerizable 3'- and 5'-O-acyl-nucleoside derivatives has been developed from inosine and 2'-deoxyuridine by enzyme-catalyzed regioselective acylation with divinyl dicarboxylates. In acetone, Lipozyme (immobilized lipase from Mucor miehei) gave 5'-O-acyl-nucleoside products, and PPL (lipase from porcine pancreas) provided 3'-O-acyl-nucleoside products.
Sun
Xiao-Feng
XF
Department of Chemistry, Zhejiang University, Hangzhou 310027, P.R. China.
Wang
Na
N
Wu
Qi
Q
Lin
Xian-Fu
XF
D000096:Acetone / Q000737:chemistry*; D000215:Acylation; D000818:Animals; D004789:Enzyme Activation; D004951:Esterification; D017665:Hydroxyl Radical; D008049:Lipase / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis*; D010179:Pancreas / Q000201:enzymology; D011108:Polymers / Q000138:chemical synthesis; D013379:Substrate Specificity; D013552:Swine; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D009705:Nucleosides; D011108:Polymers; D014753:Vinyl Compounds; D000096:Acetone; D017665:Hydroxyl Radical; C093666:Lipozyme; D008049:Lipase