The effects of protecting and acyl groups on the conformation of benzyl α-Lrhamnopyranosides: An in silico study

Farzana, Islam and Rezaur, Rahman and Mohammed, M. Matin (2021) The effects of protecting and acyl groups on the conformation of benzyl α-Lrhamnopyranosides: An in silico study. Turkish Computational and Theoretical Chemistry, 5 (1). pp. 39-50. ISSN 2602-3237

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Abstract

Carbohydrate fatty acid (CFA) esters especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature showed broader applications including anticancer activities. It was reported that appropriate conformation is needed for better activities and conformational distortion reduced antimicrobial functionality. In this context, two different esters series of benzyl α-L-rhamnopyranosides, one with 2,3-O-acetonide group and the other one without acetonide group, were subjected for the density functional theory (DFT) optimization. The optimized structures with 2,3-O-acetonide rhamnopyranoside clearly showed distortion from the regular 1C4 chair conformation while rhamnopyranoside esters without 2,3-O-acetonide functionality exhibited almost regular 1C4 chair conformation. Also, the number and position of acyl group(s) present in the benzyl rhamnopyranoside imposes a small effect on their pyranose chair conformation. Thermodynamic properties including frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) of both the series of rhamnopyranosides are also discussed which indicated that 4-O-acyl rhamnopyranosides are more reactive than the 3-O-acyl analogues.

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