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An Optimized Facile Procedure to Synthesize and Purify Allicin
Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154629/ https://www.ncbi.nlm.nih.gov/pubmed/28489057 http://dx.doi.org/10.3390/molecules22050770 |
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author | Albrecht, Frank Leontiev, Roman Jacob, Claus Slusarenko, Alan J. |
author_facet | Albrecht, Frank Leontiev, Roman Jacob, Claus Slusarenko, Alan J. |
author_sort | Albrecht, Frank |
collection | PubMed |
description | Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by H(2)O(2) using acetic acid as a catalyst was published in 2001 by Lawson and Wang. Here we report on improvements to this basic method, clarify the mechanism of the reaction and show that it is zero-order with respect to DADS and first-order with respect to the concentration of H(2)O(2). The progress of allicin synthesis and the reaction mechanism were analyzsd by high-performance liquid chromatography (HPLC) and the identity and purity of the products was verified with LC-MS and (1)H-NMR. We were able to obtain allicin of high purity (>98%) and >91% yield, with standard equipment available in any reasonable biological laboratory. This protocol will enable researchers to prepare and work with easily and cheaply prepared allicin of high quality. |
format | Online Article Text |
id | pubmed-6154629 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61546292018-11-13 An Optimized Facile Procedure to Synthesize and Purify Allicin Albrecht, Frank Leontiev, Roman Jacob, Claus Slusarenko, Alan J. Molecules Article Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by H(2)O(2) using acetic acid as a catalyst was published in 2001 by Lawson and Wang. Here we report on improvements to this basic method, clarify the mechanism of the reaction and show that it is zero-order with respect to DADS and first-order with respect to the concentration of H(2)O(2). The progress of allicin synthesis and the reaction mechanism were analyzsd by high-performance liquid chromatography (HPLC) and the identity and purity of the products was verified with LC-MS and (1)H-NMR. We were able to obtain allicin of high purity (>98%) and >91% yield, with standard equipment available in any reasonable biological laboratory. This protocol will enable researchers to prepare and work with easily and cheaply prepared allicin of high quality. MDPI 2017-05-10 /pmc/articles/PMC6154629/ /pubmed/28489057 http://dx.doi.org/10.3390/molecules22050770 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Albrecht, Frank Leontiev, Roman Jacob, Claus Slusarenko, Alan J. An Optimized Facile Procedure to Synthesize and Purify Allicin |
title | An Optimized Facile Procedure to Synthesize and Purify Allicin |
title_full | An Optimized Facile Procedure to Synthesize and Purify Allicin |
title_fullStr | An Optimized Facile Procedure to Synthesize and Purify Allicin |
title_full_unstemmed | An Optimized Facile Procedure to Synthesize and Purify Allicin |
title_short | An Optimized Facile Procedure to Synthesize and Purify Allicin |
title_sort | optimized facile procedure to synthesize and purify allicin |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154629/ https://www.ncbi.nlm.nih.gov/pubmed/28489057 http://dx.doi.org/10.3390/molecules22050770 |
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