Suppr超能文献

Regioselective alcoholysis of silychristin acetates catalyzed by lipases.

作者信息

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

机构信息

Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20 Prague, Czech Republic.

Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, I 20131 Milano, Italy.

出版信息

Int J Mol Sci. 2015 May 26;16(6):11983-95. doi: 10.3390/ijms160611983.

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.

摘要
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbd9/4490424/84685c5be20d/ijms-16-11983-g001.jpg

相似文献

1
Regioselective alcoholysis of silychristin acetates catalyzed by lipases.
Int J Mol Sci. 2015 May 26;16(6):11983-95. doi: 10.3390/ijms160611983.
2
Highly regioselective synthesis of 3'-O-acyl-trifluridines catalyzed by Pseudomonas cepacia lipase.
Appl Biochem Biotechnol. 2011 Nov;165(5-6):1161-8. doi: 10.1007/s12010-011-9333-9. Epub 2011 Aug 6.
3
The acetates of p-nitrophenyl alpha-L-arabinofuranoside--regioselective preparation by action of lipases.
Bioorg Med Chem. 2006 Mar 15;14(6):1805-10. doi: 10.1016/j.bmc.2005.10.023. Epub 2005 Nov 8.
4
Kinetic modeling and docking study of immobilized lipase catalyzed synthesis of furfuryl acetate.
Enzyme Microb Technol. 2016 Mar;84:1-10. doi: 10.1016/j.enzmictec.2015.12.003. Epub 2015 Dec 7.
6
Regioselectivity-reversal in acylation of 6-azauridine catalyzed by Burkholderia cepacia lipase.
Biotechnol Lett. 2012 Jan;34(1):55-9. doi: 10.1007/s10529-011-0737-y. Epub 2011 Sep 6.
8
Biodiesel production from Jatropha oil catalyzed by immobilized Burkholderia cepacia lipase on modified attapulgite.
Bioresour Technol. 2013 Nov;148:202-7. doi: 10.1016/j.biortech.2013.08.143. Epub 2013 Sep 2.
9
10
Efficient regioselective synthesis of 3'-O-crotonylfloxuridine catalysed by Pseudomonas cepacia lipase.
Biotechnol Appl Biochem. 2009 Jan;52(Pt 1):45-51. doi: 10.1042/BA20080018.

引用本文的文献

1
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners.
Int J Mol Sci. 2021 Jul 23;22(15):7885. doi: 10.3390/ijms22157885.

本文引用的文献

1
Chemistry of silybin.
Nat Prod Rep. 2014 Sep;31(9):1138-57. doi: 10.1039/c3np70122k.
2
Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers.
Molecules. 2014 Apr 2;19(4):4115-34. doi: 10.3390/molecules19044115.
3
Enzymatic kinetic resolution of silybin diastereoisomers.
J Nat Prod. 2010 Apr 23;73(4):613-9. doi: 10.1021/np900758d.
4
Silybin and silymarin--new and emerging applications in medicine.
Curr Med Chem. 2007;14(3):315-38. doi: 10.2174/092986707779941159.
5
Silymarin and its components scavenge phenylglyoxylic ketyl radicals.
Fitoterapia. 2006 Dec;77(7-8):525-9. doi: 10.1016/j.fitote.2006.06.005. Epub 2006 Jul 6.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验