Controllable synthesis of polymerizable ester and amide prodrugs of acyclovir by enzyme in organic solvent.
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.
Li
Xia
X
Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
Wu
Qi
Q
Lv
De-shui
DS
Lin
Xian-fu
XF
D000212:Acyclovir / Q000138:chemical synthesis* / Q000737:chemistry; D000215:Acylation; D000577:Amides / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis; D004952:Esters / Q000138:chemical synthesis*; D005658:Fungi / Q000201:enzymology; D008049:Lipase / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
D000577:Amides; D000998:Antiviral Agents; D004952:Esters; D009930:Organic Chemicals; D011108:Polymers; D011355:Prodrugs; D012997:Solvents; D008049:Lipase; D000212:Acyclovir