Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives

<p class="orbitalabstract">4-O-Palmitoylation of methyl a-L-rhamnopyranoside (<strong>2</strong>) was carried out via blocking-deblocking technique. Methyl a-L-rhamnopyranoside (<strong>2</strong>) was first converted into 2,3-O-isopropylidene derivative (<...

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Main Author: Mohammed Mahbubul Matin
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2014-05-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/553
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spelling doaj-7f9e90bf4b4a4c7ba150dc1d4313faad2021-07-07T19:22:35ZengUniversidade Federal de Mato Grosso do SulOrbital: The Electronic Journal of Chemistry1984-64282014-05-0161202810.17807/orbital.v6i1.553238Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside DerivativesMohammed Mahbubul Matin0Organic Research Laboratory, Department of Chemistry, University of Chittagong, Chittagong 4331,<p class="orbitalabstract">4-O-Palmitoylation of methyl a-L-rhamnopyranoside (<strong>2</strong>) was carried out via blocking-deblocking technique. Methyl a-L-rhamnopyranoside (<strong>2</strong>) was first converted into 2,3-O-isopropylidene derivative (<strong>5</strong>) which on palmitoylation followed by deacetonation gave the desired 4-O-palmitoylrhamnopyranoside (<strong>7</strong>) in good yield. A number of 2,3-di-O-acyl derivatives of <strong>7</strong> were also prepared to get newer rhamnopyranosides (<strong>8</strong>-<strong>14</strong>) of biological importance. All the rhamnopyranosides (<strong>2</strong>, <strong>5</strong>-<strong>14</strong>) were employed as test chemicals for in vitro antibacterial and antifungal functionality test against ten human pathogenic bacteria and four fungi, respectively. The study revealed that some of the tested rhamnopyranoside derivatives showed excellent antimicrobial functionalities as compared to the standard antibiotic.</p>http://orbital.ufms.br/index.php/Chemistry/article/view/553methyl α-l-rhamnopyranosidepalmitoylationantimicrobial activitiesstructure activity relationship
collection DOAJ
language English
format Article
sources DOAJ
author Mohammed Mahbubul Matin
spellingShingle Mohammed Mahbubul Matin
Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
Orbital: The Electronic Journal of Chemistry
methyl α-l-rhamnopyranoside
palmitoylation
antimicrobial activities
structure activity relationship
author_facet Mohammed Mahbubul Matin
author_sort Mohammed Mahbubul Matin
title Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
title_short Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
title_full Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
title_fullStr Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
title_full_unstemmed Synthesis and Antimicrobial Study of Some Methyl 4-O-palmitoyl-α-L-rhamnopyranoside Derivatives
title_sort synthesis and antimicrobial study of some methyl 4-o-palmitoyl-α-l-rhamnopyranoside derivatives
publisher Universidade Federal de Mato Grosso do Sul
series Orbital: The Electronic Journal of Chemistry
issn 1984-6428
publishDate 2014-05-01
description <p class="orbitalabstract">4-O-Palmitoylation of methyl a-L-rhamnopyranoside (<strong>2</strong>) was carried out via blocking-deblocking technique. Methyl a-L-rhamnopyranoside (<strong>2</strong>) was first converted into 2,3-O-isopropylidene derivative (<strong>5</strong>) which on palmitoylation followed by deacetonation gave the desired 4-O-palmitoylrhamnopyranoside (<strong>7</strong>) in good yield. A number of 2,3-di-O-acyl derivatives of <strong>7</strong> were also prepared to get newer rhamnopyranosides (<strong>8</strong>-<strong>14</strong>) of biological importance. All the rhamnopyranosides (<strong>2</strong>, <strong>5</strong>-<strong>14</strong>) were employed as test chemicals for in vitro antibacterial and antifungal functionality test against ten human pathogenic bacteria and four fungi, respectively. The study revealed that some of the tested rhamnopyranoside derivatives showed excellent antimicrobial functionalities as compared to the standard antibiotic.</p>
topic methyl α-l-rhamnopyranoside
palmitoylation
antimicrobial activities
structure activity relationship
url http://orbital.ufms.br/index.php/Chemistry/article/view/553
work_keys_str_mv AT mohammedmahbubulmatin synthesisandantimicrobialstudyofsomemethyl4opalmitoylalrhamnopyranosidederivatives
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