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

Authors : Farzana ISLAM, Md Rezaur RAHMAN, Mohammed Mahbubul MATİN

Pages : 39-50

Doi:10.33435/tcandtc.914768

View : 44 | Download : 17

Publication Date : 2021-06-15

Article Type : Research Paper

Abstract :Carbohydrate fatty acid insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values(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 groupinsert ignore into journalissuearticles values(s); present in the benzyl rhamnopyranoside imposes a small effect on their pyranose chair conformation. Thermodynamic properties including frontier molecular orbitals insert ignore into journalissuearticles values(FMO); and molecular electrostatic potential insert ignore into journalissuearticles values(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.
Keywords : Conformational study, DFT optimization, MEP, Rhamnopyranoside, Sugar esters SEs, Thermodynamic properties

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