Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1
Lipase B from Candida anturctica has been shown to be an efficient catalyst for the regioselective acylation of the dammarane type glucoside ginsenoside Rg1 (1) on reaction with vinyl acetate in t-AmOH, affording the corresponding 6’-O-acetyl derivative lb in high yield. The structure of lb was dete...
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American Chemical Society
1995
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Online Access: | http://hdl.handle.net/2434/178342 https://doi.org/10.1021/jo00117a012 |
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ftunivmilanoair:oai:air.unimi.it:2434/178342 2024-02-11T09:56:29+01:00 Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 B. Danieli E. Ragg L. Scaglioni M. Luisetti S. Riva A. Bertinotti E. Bombardelli B. Danieli M. Luisetti S. Riva A. Bertinotti E. Ragg L. Scaglioni E. Bombardelli 1995-06-16 http://hdl.handle.net/2434/178342 https://doi.org/10.1021/jo00117a012 eng eng American Chemical Society info:eu-repo/semantics/altIdentifier/wos/WOS:A1995RE01600012 volume:60 issue:12 firstpage:3637 lastpage:3642 journal:JOURNAL OF ORGANIC CHEMISTRY http://hdl.handle.net/2434/178342 doi:10.1021/jo00117a012 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0029072107 ginsenoside lipase B Candida antarctica regio-selective acylation Settore CHIM/06 - Chimica Organica info:eu-repo/semantics/article 1995 ftunivmilanoair https://doi.org/10.1021/jo00117a012 2024-01-23T23:24:56Z Lipase B from Candida anturctica has been shown to be an efficient catalyst for the regioselective acylation of the dammarane type glucoside ginsenoside Rg1 (1) on reaction with vinyl acetate in t-AmOH, affording the corresponding 6’-O-acetyl derivative lb in high yield. The structure of lb was determined through a careful inspection of its lH NMR at 600 MHz, which allowed for the complete assignment of the signals of the sugar’s protons. The introduction of a carboxyacetyl residue was then investigated using different protocols. The best results were obtained with a two-step sequence involving the preliminary enzymatic acylation of 1 with bis(2,2,2-trichloroethyl) malonate to give the mixed malonyl derivative lf, followed by selective chemical hydrolysis with ZdAcOH to the 6’-O-carboxyacetyl ginsenoside Rg1 (le). Article in Journal/Newspaper Antarc* Antarctica The University of Milan: Archivio Istituzionale della Ricerca (AIR) The Journal of Organic Chemistry 60 12 3637 3642 |
institution |
Open Polar |
collection |
The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
op_collection_id |
ftunivmilanoair |
language |
English |
topic |
ginsenoside lipase B Candida antarctica regio-selective acylation Settore CHIM/06 - Chimica Organica |
spellingShingle |
ginsenoside lipase B Candida antarctica regio-selective acylation Settore CHIM/06 - Chimica Organica B. Danieli E. Ragg L. Scaglioni M. Luisetti S. Riva A. Bertinotti E. Bombardelli Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
topic_facet |
ginsenoside lipase B Candida antarctica regio-selective acylation Settore CHIM/06 - Chimica Organica |
description |
Lipase B from Candida anturctica has been shown to be an efficient catalyst for the regioselective acylation of the dammarane type glucoside ginsenoside Rg1 (1) on reaction with vinyl acetate in t-AmOH, affording the corresponding 6’-O-acetyl derivative lb in high yield. The structure of lb was determined through a careful inspection of its lH NMR at 600 MHz, which allowed for the complete assignment of the signals of the sugar’s protons. The introduction of a carboxyacetyl residue was then investigated using different protocols. The best results were obtained with a two-step sequence involving the preliminary enzymatic acylation of 1 with bis(2,2,2-trichloroethyl) malonate to give the mixed malonyl derivative lf, followed by selective chemical hydrolysis with ZdAcOH to the 6’-O-carboxyacetyl ginsenoside Rg1 (le). |
author2 |
B. Danieli M. Luisetti S. Riva A. Bertinotti E. Ragg L. Scaglioni E. Bombardelli |
format |
Article in Journal/Newspaper |
author |
B. Danieli E. Ragg L. Scaglioni M. Luisetti S. Riva A. Bertinotti E. Bombardelli |
author_facet |
B. Danieli E. Ragg L. Scaglioni M. Luisetti S. Riva A. Bertinotti E. Bombardelli |
author_sort |
B. Danieli |
title |
Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
title_short |
Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
title_full |
Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
title_fullStr |
Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
title_full_unstemmed |
Regioselective Enzyme-Mediated Acylation of Polyhydroxy Natural Compounds. A Remarkable, Highly Efficient Preparation of 6'-Acetyl and 6'-O-Carboxyacetyl Ginsenoside Rg1 |
title_sort |
regioselective enzyme-mediated acylation of polyhydroxy natural compounds. a remarkable, highly efficient preparation of 6'-acetyl and 6'-o-carboxyacetyl ginsenoside rg1 |
publisher |
American Chemical Society |
publishDate |
1995 |
url |
http://hdl.handle.net/2434/178342 https://doi.org/10.1021/jo00117a012 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:A1995RE01600012 volume:60 issue:12 firstpage:3637 lastpage:3642 journal:JOURNAL OF ORGANIC CHEMISTRY http://hdl.handle.net/2434/178342 doi:10.1021/jo00117a012 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0029072107 |
op_doi |
https://doi.org/10.1021/jo00117a012 |
container_title |
The Journal of Organic Chemistry |
container_volume |
60 |
container_issue |
12 |
container_start_page |
3637 |
op_container_end_page |
3642 |
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1790603479749754880 |