The structure activity relationship (SAR) study revealed that incorporation of 4-O-lauroyl group in rhamnopyranoside frame work along with 2,3-di-O-acyl group increased the antifungal potentiality of the rhamnopyranosides. | Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents Current Chemistry Letters 6 2017 31 40 Contents lists available at GrowingScience Current Chemistry Letters homepage Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents Mohammed M. Matina Mohammad . Bhuiyana Abul . Azada and Nishat Aktherb a Organic Research Laboratory Department of Chemistry University of Chittagong Chittagong-4331 Bangladesh b Department of Biochemistry and Molecular Biology Mawlana Bhashani Science and Technology University Tangail-1902 Bangladesh CHRONICLE ABSTRACT Article history Benzyl -L-rhamnopyranoside prepared by both conventional and microwave assisted Received August 21 2016 glycosidation techniques was converted into benzyl 2 3-O-isopropylidene-α-L- Received in revised form rhamnopyranoside which after lauroylation followed by removal of isopropylidene group gave October 14 2016 the benzyl 4-O-lauroyl-α-L-rhamnopyranoside in good yield. Several derivatives of benzyl 4- Accepted 15 October 2016 O-lauroyl-α-L-rhamnopyranoside were prepared and assessed in vitro for their antimicrobial Available online 15 October 2016 activity against ten human pathogenic bacteria and seven fungi. The structure activity relationship SAR study revealed that incorporation of 4-O-lauroyl group in Keywords Benzyl α-L-rhamnopyranoside rhamnopyranoside frame work along with 2 3-di-O-acyl group increased the antifungal Lauroylation potentiality of the rhamnopyranosides. Antimicrobial agents Structure activity relationship SAR 2017 Growing Science Ltd. All rights reserved. 1. Introduction L-Rhamnose an important member of the monosaccharide series 1 is widely distributed in nature it was found in plant gums plant glycosides and in bacterial 2 Some disaccharides having L-rhamnose as the aglycone has been synthesized and are important for the determination of the .
