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Controllable Selective Synthesis of a Polymerizable Prodrug of Cytarabine by Enzymatic and Chemical Methods

Controllable Selective Synthesis of a Polymerizable Prodrug of Cytarabine by Enzymatic and Chemical Methods

Na Wang, Zhi Chun Chen, De Shui Lu, Xian Fu Lin

Bioorg Med Chem Lett. 2005 Sep 15;15(18):4064-7.

PMID: 16005210

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP9001621-C	Lipase acrylic resin		9001-62-1	Price

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