Effective enzymatic caffeoylation of natural glucopyranosides

  • Bioorg Med Chem Lett. 2016 Mar 15;26(6):1567-1570. doi: 10.1016/j.bmcl.2016.02.010.
Andrej Chyba  1 ,  Vladimír Mastihuba  1 ,  Mária Mastihubová  2
Affiliations
  • 1. Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38 Bratislava, Slovakia.
  • 2. Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38 Bratislava, Slovakia. Electronic address: [email protected].
PMID: 26896186 DOI: 10.1016/j.bmcl.2016.02.010
Abstract

Reaction system was developed for enzymatic caffeoylation of model saccharidic acceptor methyl β-d-glucopyranoside to obtain exclusively methyl 6-O-caffeoyl-β-D-glucopyranoside. Reaction with starting concentration of acceptor 0.2 M provided 73% yield of purified product within 17 days. Reactions with low acceptor concentrations (0.04 and 0.08 M) run to the completion within 7 days. Such highly effective and regioselective reaction was promoted by Lipozyme TL IM in tert-butanol, using vinyl caffeate as acylation donor. The optimized reaction conditions were used in preparative caffeoylation of natural substances-arbutin and salidroside, giving 75% of 6-O-caffeoylated arbutin (robustaside B) and 74% of 6-O-caffeoylated salidroside as the only products after 12 and 16 days, respectively.

Keywords
6-O-Caffeoyl-salidroside; Lipozyme TL IM; Phenylpropanoid glycosides; Regioselective caffeoylation; Robustaside B.
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