International Journal of Molecular Sciences 2015-01-01

Regioselective alcoholysis of silychristin acetates catalyzed by lipases.

Eva Vavříková, Paolo Gavezzotti, Kateřina Purchartová, Kateřina Fuksová, David Biedermann, Marek Kuzma, Sergio Riva, Vladimír Křen

Index: Int. J. Mol. Sci. 16 , 11983-95, (2015)

Full Text: HTML

Abstract

A panel of lipases was screened for the selective acetylation and alcoholysis of silychristin and silychristin peracetate, respectively. Acetylation at primary alcoholic group (C-22) of silychristin was accomplished by lipase PS (Pseudomonas cepacia) immobilized on diatomite using vinyl acetate as an acetyl donor, whereas selective deacetylation of 22-O-acetyl silychristin was accomplished by Novozym 435 in methyl tert-butyl ether/ n-butanol. Both of these reactions occurred without diastereomeric discrimination of silychristin A and B. Both of these enzymes were found to be capable to regioselective deacetylation of hexaacetyl silychristin to afford penta-, tetra- and tri-acetyl derivatives, which could be obtained as pure synthons for further selective modifications of the parent molecule.

Related Compounds

  • Chloroform
  • Acetone
  • DIMETHYL SUL...
  • Acetonitrile
  • Methanol
  • sodium dodecyl sul...
  • Toluene
  • vinyl acetate

Related Articles:

A survey of the interactome of Kaposi's sarcoma-associated herpesvirus ORF45 revealed its binding to viral ORF33 and cellular USP7, resulting in stabilization of ORF33 that is required for production of progeny viruses.

2015-05-01

[J. Virol. 89(9) , 4918-31, (2015)]

Aqueous-core PEG-coated PLA nanocapsules for an efficient entrapment of water soluble anticancer drugs and a smart therapeutic response.

2015-01-01

[Eur. J. Pharm. Biopharm. 89 , 30-9, (2015)]

SSX2 is a novel DNA-binding protein that antagonizes polycomb group body formation and gene repression.

2015-01-01

[Nucleic Acids Res. 42(18) , 11433-46, (2014)]

The dynamics of giant unilamellar vesicle oxidation probed by morphological transitions.

2014-10-01

[Biochim. Biophys. Acta 1838(10) , 2615-24, (2014)]

The dual FAAH/MAGL inhibitor JZL195 has enhanced effects on endocannabinoid transmission and motor behavior in rats as compared to those of the MAGL inhibitor JZL184.

2014-09-01

[Pharmacol. Biochem. Behav. 124 , 153-9, (2014)]

More Articles...