TY - JOUR
T1 - Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step
AU - Hanamura, Shun
AU - Hanaya, Kengo
AU - Shoji, Mitsuru
AU - Sugai, Takeshi
N1 - Funding Information:
We thank Professor Hiroki Hamada of Okayama Science University for discussion, and Novozymes Japan for generous gift of Novozym 435, and Amano Enzyme Inc. for lipase PS-IM. Mr. Susanta Mandal’s contribution in the early phase of this work is appreciated. This work was supported both by a Grant-in-Aid for Scientific Research (No. 26450143 ) and Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology , Japan, and is gratefully acknowledged.
Publisher Copyright:
© 2016 Elsevier B.V. All rights reserved.
PY - 2016/6/1
Y1 - 2016/6/1
N2 - Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.
AB - Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.
KW - Glycosylated form
KW - Lipase
KW - Polyphenol
KW - Regioselective reaction
KW - Transesterification
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U2 - 10.1016/j.molcatb.2016.03.001
DO - 10.1016/j.molcatb.2016.03.001
M3 - Article
AN - SCOPUS:84961839117
SN - 1381-1177
VL - 128
SP - 19
EP - 26
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
ER -