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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...

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Autores principales: Albrecht, Frank, Leontiev, Roman, Jacob, Claus, Slusarenko, Alan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
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.
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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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