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2000
Volume 21, Issue 5
  • ISSN: 1573-4064
  • E-ISSN: 1875-6638

Abstract

Background

The approval of Sucrose Fatty Acid Esters (SFAEs) as food additives/preservatives with antimicrobial potential has triggered enormous interest in discovering new biological applications. Accordingly, many researchers reported that SFAEs consist of various sugar moieties, and hydrophobic side chains are highly active against certain fungal species.

Objective

This study aimed to conduct aregioselective synthesis of SAFE and check the effect of chain length and site of acylation (., C-6 . C-2, C-3, C-4, and long-chain . short-chain) on antimicrobial potency.

Methods

A direct acylation method maintaining several conditions was used for esterification. tests, molecular docking, and studies were conducted using standard procedures.

Results

tests revealed that the fatty acid chain length in mannopyranoside esters significantly affects the antifungal activity, where C12 chains are more potent against Aspergillus species. In terms of acylation site, mannopyranoside esters with a C8 chain substituted at the C-6 position are more active in antifungal inhibition. Molecular docking also revealed that these mannopyranoside esters had comparatively better stable binding energy and hence better inhibition, with the fungal enzymes lanosterol 14-alpha-demethylase (3LD6), urate oxidase (1R51), and glucoamylase (1KUL) than the standard antifungal drug fluconazole. Additionally, the thermodynamic, orbital, drug-likeness, and safety profiles of these mannopyranoside esters were calculated and discussed, along with the Structure-Activity Relationships (SAR).

Conclusion

This study thus highlights the importance of the acylation site and lipid-like fatty acid chain length that govern the antimicrobial activity of mannopyranoside-based SFAE.

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Efficient Synthesis of Mannopyranoside-based Fatty Acyl Esters: Effects of Acyl Groups on Antimicrobial Potential
Med. Chem. 21, 385 (2025); https://doi.org/10.2174/0115734064292665240523113515
/content/journals/mc/10.2174/0115734064292665240523113515
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  • Article Type:     Research Article
Keyword(s): ADMET; antimicrobial agents; effects of chain length; molecular docking; regioselective acylation; structure-activity relationship; sugar fatty acid ester (SFAE)

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