title: Controllable selective synthesis of a polymerizable prodrug of cytarabine by enzymatic and chemical methods.
abstract: Selectivity of enzymatic and chemical methods for transesterifications of cytarabine with divinyl dicarboxylates was described. Catalysis by lipase acrylic resin from Candida antarctica (CAL-B) in acetone facilitated the single step synthesis of polymerizable 5'-O-acyl cytarabine derivatives in high yields, while the use of alkaline protease from Bacillus subtilis (subtilisin) in pyridine afforded the mixture products of 5'-O-acyl and 4-N-acyl cytarabine derivatives. Interestingly, polymerizable 4-N-acyl cytarabine vinyl derivatives can be selectively prepared by chemical transesterification in dioxane. The obtained series of cytarabine derivatives would be useful for a significant monomer for a polymeric anticancer drug.
authors: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
authors: Na
authors: N
authors: Wang
authors: Zhi Chun
authors: ZC
authors: Chen
authors: De Shui
authors: DS
authors: Lu
authors: Xian Fu
authors: XF
authors: Lin
mesh_terms: D000215:Acylation; D000964:Antimetabolites, Antineoplastic / Q000737:chemistry / Q000378:metabolism; D001412:Bacillus subtilis / Q000201:enzymology; D001426:Bacterial Proteins / Q000378:metabolism; D003561:Cytarabine / Q000737:chemistry / Q000378:metabolism*; D010450:Endopeptidases / Q000378:metabolism; D004952:Esters / Q000737:chemistry; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000964:Antimetabolites, Antineoplastic; D001426:Bacterial Proteins; D004952:Esters; D005656:Fungal Proteins; D011108:Polymers; D011355:Prodrugs; D003561:Cytarabine; C093666:Lipozyme; D008049:Lipase; C431349:lipase B, Candida antarctica; D010450:Endopeptidases; C087822:alkaline protease