Highly regioselective enzymatic synthesis of polymerizable derivatives of methyl shikimate.
Regiocontrollable selectivity of enzymatic method for synthesis of polymerizable derivatives of methyl shikimate was described. Lipase acrylic resin from Candida antarctica (CAL-B) and immobilized lipase from Mucor miehei (MML) showed high regioselectivity toward the secondary hydroxyl of methyl shikimate, which presents three hydroxyl groups with similar reactivity. Catalysis by MML in acetone facilitated the single step synthesis of 5-O-acyl methyl shikimate derivatives in high yields, while the use of CAL-B in acetone afforded 4-O-acyl methyl shikimate derivatives. The obtained series of methyl shikimate derivatives would be important monomers for potential useful analogues of shikimic acid.
Li
Chao
C
Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu 610064, PR China.
Wang
Hai-Yang
HY
Wang
Na
N
Fang
Yu-Guo
YG
Chen
Xi
X
Yu
Xiao-Qi
XQ
D001704:Biopolymers / Q000737:chemistry; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009089:Mucor / Q000201:enzymology; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D012997:Solvents; D013237:Stereoisomerism
D001704:Biopolymers; D012997:Solvents; C453473:methyl shikimate; D012765:Shikimic Acid; D008049:Lipase