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Controllable Synthesis of Polymerizable Ester and Amide Prodrugs of Acyclovir by Enzyme in Organic Solvent

Controllable Synthesis of Polymerizable Ester and Amide Prodrugs of Acyclovir by Enzyme in Organic Solvent

Xia Li, Qi Wu, De-shui Lv, Xian-fu Lin

Bioorg Med Chem. 2006 May 15;14(10):3377-82.

PMID: 16431120

Abstract:

A facile control of the acylation position at the primary hydroxyl and amino of acyclovir, respectively, was achieved and five polymerizable acyclovir prodrugs were synthesized. Various reaction conditions were studied in detail. Thus, lipase acrylic resin from Candida antarctica (CAL-B) in pyridine or acetone showed high chemo-selectivity toward the primary hydroxyl of acyclovir. However, lipase PS 'Amano' (PS) in DMSO selectively acylated the amino group. The selectivity of PS could be adjusted by changing reaction solvents. The acyclovir vinyl derivatives obtained would be important monomers used for the preparation of macromolecular nucleoside drugs.

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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