Novel enzymatic synthesis of 4-O-cinnamoyl quinic and shikimic acid derivatives.
The first direct synthesis of 4-O-cinnamoyl derivatives of quinic and shikimic acids were accomplished by regioselective esterification with Candida antarctica lipase A. For hydrocinnamic esters, enzymatic transesterification with vinyl esters gave excellent yields. However, more reactive acylating agents such as anhydrides were used to synthesize cinnamic derivatives of both acids. An inhibitory effect was observed with this lipase for p-methoxy, p-hydroxy, and p-acetoxy vinyl ester and anhydride derivatives (coumarate and ferulate derivatives).
Armesto
Nuria
N
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
Ferrero
Miguel
M
Fernández
Susana
S
Gotor
Vicente
V
D000215:Acylation; D000890:Anti-Infective Agents / Q000138:chemical synthesis; D002175:Candida / Q000201:enzymology; D002934:Cinnamates; D004800:Enzymes, Immobilized / Q000378:metabolism; D004951:Esterification; D008049:Lipase / Q000378:metabolism; D010944:Plants / Q000378:metabolism; D011801:Quinic Acid / Q000138:chemical synthesis*; D012765:Shikimic Acid / Q000138:chemical synthesis*
D000890:Anti-Infective Agents; D002934:Cinnamates; D004800:Enzymes, Immobilized; D011801:Quinic Acid; D012765:Shikimic Acid; D008049:Lipase