Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 19-26 |
| Number of pages | 8 |
| Journal | Journal of Molecular Catalysis B: Enzymatic |
| Volume | 128 |
| DOIs | |
| Publication status | Published - 2016 Jun 1 |
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Keywords
- Glycosylated form
- Lipase
- Polyphenol
- Regioselective reaction
- Transesterification
ASJC Scopus subject areas
- Biochemistry
- Bioengineering
- Catalysis
- Process Chemistry and Technology
Cite this
Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step. / Hanamura, Shun; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi.
In: Journal of Molecular Catalysis B: Enzymatic, Vol. 128, 01.06.2016, p. 19-26.Research output: Contribution to journal › Article
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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
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
UR - http://www.scopus.com/inward/record.url?scp=84961839117&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84961839117&partnerID=8YFLogxK
U2 - 10.1016/j.molcatb.2016.03.001
DO - 10.1016/j.molcatb.2016.03.001
M3 - Article
AN - SCOPUS:84961839117
VL - 128
SP - 19
EP - 26
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
SN - 1381-1177
ER -