Glycosyl donor

Glycosyl donor

The Chemical Synthesis of Lipid A

Published in Helmut Brade, Steven M. Opal, Stefanie N. Vogel, David C. Morrison, Endotoxin in Health and Disease, 2020

Shoichi Kusumoto, Koichi Fukase, Masato Oikawa

The PE analogs of E. coli-type and the biosynthetic precursor-type acylation patterns (17 and 18, respectively) were synthesized by a strategy basically similar to that employed in the early synthesis of lipid A (1,2), except for the timing of phosphorylation (39,40). Thus, in the case of 17, a glucosamine derivative (Fig. 10, 19), which contains two acyl groups, and protected phosphonooxyethyl group was prepared and coupled with the same glycosyl donor (Fig. 3, 3) used previously to form the β(l-6) disaccharide backbone. The reaction sequence leading to the final product was straightforward (Fig. 10): removal of the N-Troc function followed by N-acylation and deprotection readily gave 17, which was purified by simple ion-exchange chromatography.

The role of UDP-glycosyltransferases in xenobioticresistance

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Journal Information

Published in Drug Metabolism Reviews, 2022

Diana Dimunová, Petra Matoušková, Radka Podlipná, Iva Boušová, Lenka Skálová

The glucosyltransferase OleD in Streptomyces antibioticus catalyzes the glucosylation of oleandomycin using UDP-glucose (UDP-Glc) as the glycosyl donor. This enzyme serves for macrolide inactivation in macrolide-producing microorganisms, but it displays a relatively broad substrate tolerance with a bias toward small aromatic hydroxyl groups, including polyphenols (like daidzein, resveratrol) as well as other aromatic compounds (methylestradiol) (Zhou et al. 2013).

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The Chemical Synthesis of Lipid A

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