Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides
<p>Application of carbohydrate fatty acid (CFA) esters in food and beverage industries has increased their interest in other fields. Especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature had broader applications including anticancer activities. Benzyl α-L-rhamnop...
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Universidade Federal de Mato Grosso do Sul
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doaj-9f0700498a254eb2be6fc05d66f980772021-07-07T19:22:41ZengUniversidade Federal de Mato Grosso do SulOrbital: The Electronic Journal of Chemistry1984-64282021-07-0113325025810.17807/orbital.v13i3.1614666Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosidesDeen Muhammad0Mohammed M. Matin1Sheikh Md. Rasel Miah2Puja Devi3University of ChittagongUniversity of ChittagongUniversity of ChittagongUniversity of Chittagong<p>Application of carbohydrate fatty acid (CFA) esters in food and beverage industries has increased their interest in other fields. Especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature had broader applications including anticancer activities. Benzyl α-L-rhamnopyranoside, prepared from L-rhamnose, on 2,3-<em>O</em>-isopropylidene protection with 2,2-dimethoxypropane followed by acylation at C-4 hydroxyl position with different acylating agents furnished the corresponding 4-<em>O</em>-acyl-α-L-rhamnopyranosides in good yields. All the compounds were well characterized by spectroscopic techniques. <em>In vitro</em> antimicrobial activities against eight bacterial and two fungal pathogens indicated that these 2,3-<em>O</em>-isopropylidene protected rhamnopyranosides had weak to moderate inhibitory properties. To rationalize such moderate activities structural (conformational) distortion of these monoacetonide protected CFA esters were studied from the density functional theory (DFT) optimized structures. In addition, thermodynamic properties including frontier molecular orbitals of the synthesized rhamnopyranosides were calculated and discussed. Corroboration of all the studies signifies that the moderate antimicrobial efficacy of the isopropylidene protected rhamnopyranosides might be due to their distorted conformations, lower softness and smaller dipole moments.</p><p> </p><p>DOI: <a href="http://dx.doi.org/10.17807/orbital.v13i3.1614">http://dx.doi.org/10.17807/orbital.v13i3.1614</a></p>http://orbital.ufms.br/index.php/Chemistry/article/view/1614acylationantimicrobial agentbenzyl α-l-rhamnopyranosideconformational studyhomo-lumothermodynamic calculations |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Deen Muhammad Mohammed M. Matin Sheikh Md. Rasel Miah Puja Devi |
spellingShingle |
Deen Muhammad Mohammed M. Matin Sheikh Md. Rasel Miah Puja Devi Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides Orbital: The Electronic Journal of Chemistry acylation antimicrobial agent benzyl α-l-rhamnopyranoside conformational study homo-lumo thermodynamic calculations |
author_facet |
Deen Muhammad Mohammed M. Matin Sheikh Md. Rasel Miah Puja Devi |
author_sort |
Deen Muhammad |
title |
Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides |
title_short |
Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides |
title_full |
Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides |
title_fullStr |
Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides |
title_full_unstemmed |
Synthesis, Antimicrobial, and DFT Studies of Some Benzyl 4-O-Acyl-α-L-rhamnopyranosides |
title_sort |
synthesis, antimicrobial, and dft studies of some benzyl 4-o-acyl-α-l-rhamnopyranosides |
publisher |
Universidade Federal de Mato Grosso do Sul |
series |
Orbital: The Electronic Journal of Chemistry |
issn |
1984-6428 |
publishDate |
2021-07-01 |
description |
<p>Application of carbohydrate fatty acid (CFA) esters in food and beverage industries has increased their interest in other fields. Especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature had broader applications including anticancer activities. Benzyl α-L-rhamnopyranoside, prepared from L-rhamnose, on 2,3-<em>O</em>-isopropylidene protection with 2,2-dimethoxypropane followed by acylation at C-4 hydroxyl position with different acylating agents furnished the corresponding 4-<em>O</em>-acyl-α-L-rhamnopyranosides in good yields. All the compounds were well characterized by spectroscopic techniques. <em>In vitro</em> antimicrobial activities against eight bacterial and two fungal pathogens indicated that these 2,3-<em>O</em>-isopropylidene protected rhamnopyranosides had weak to moderate inhibitory properties. To rationalize such moderate activities structural (conformational) distortion of these monoacetonide protected CFA esters were studied from the density functional theory (DFT) optimized structures. In addition, thermodynamic properties including frontier molecular orbitals of the synthesized rhamnopyranosides were calculated and discussed. Corroboration of all the studies signifies that the moderate antimicrobial efficacy of the isopropylidene protected rhamnopyranosides might be due to their distorted conformations, lower softness and smaller dipole moments.</p><p> </p><p>DOI: <a href="http://dx.doi.org/10.17807/orbital.v13i3.1614">http://dx.doi.org/10.17807/orbital.v13i3.1614</a></p> |
topic |
acylation antimicrobial agent benzyl α-l-rhamnopyranoside conformational study homo-lumo thermodynamic calculations |
url |
http://orbital.ufms.br/index.php/Chemistry/article/view/1614 |
work_keys_str_mv |
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