Esterase catalyzed regioselective hydrolyses of acetylated monosaccharides

Tomić, Srđanka; Ljevaković, Đurđica; Tomašić, Jelka

doi:10.1016/s0040-4020(01)80251-9

Cited by 12 publications

(7 citation statements)

References 22 publications

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“…Most of the studies have focused on the migration of acetyl, benzoyl or pivaloyl groups which are widely applied temporary protective groups in carbohydrate chemistry. 295,296,[314][315][316][317][318][319][320] Acetylated carbohydrates are found in nature, which provides additional motivation to study their explicit migration behavior. 32,285,[321][322][323][324][325][326] Reports on the migration of fatty acid esters, 31,303,327 stilbene, 328 levulinoyl, 329 alkyloxycarbonyl, 330 formyl, 283 and benzoyl derivatives 33 can be found in the literature.…”

Section: Acyl Group Scope In Migration Along Polyolsmentioning

confidence: 99%

Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions

et al. 2020

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This review is the counterpart of a 2018 Chemical Reviews article that examined the mechanisms of chemical glycosylation in the absence of stereodirecting participation. Attention is now turned to a critical review of the evidence in support of stereodirecting participation in glycosylation reactions by esters from either the vicinal or more remote positions. As participation by esters is often accompanied by ester migration, the mechanism(s) of migration are also reviewed. Esters are central to the entire review, which accordingly opens with an overview of their structure and their influence on the conformations of six-membered rings. Next the structure and relative energetics of dioxacarbeniun ions are covered with emphasis on the influence of ring size. The existing kinetic evidence for participation is then presented followed an overview of the various intermediates either isolated or characterized spectroscopically. The evidence supporting participation from remote or distal positions is critically examined and alternative hypotheses for the stereodirecting effect of such esters is presented. The mechanisms of ester migration are first examined from the perspective of glycosylation reactions, and then more broadly in the context of partially acylated polyols.

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Section: Acyl Group Scope In Migration Along Polyolsmentioning

confidence: 99%

Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions

et al. 2020

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“…The product was isolated as anomeric pale yellow oil mixture (3a, 3b) (767 mg, 82%; Anal. Calcd for C 39 Pure anomers 3a and 3b were separated from anomeric mixture using column chromatography on silica gel (diethyl ether/petroleum ether 1:1) and a/b ratio was approximately 3:1. …”

Section: Equiv) Was Suspended In Dry Dcm (5 Ml) At 0°c Under N 2 Andmentioning

confidence: 99%

Novel mannosyl derivatives of peptidoglycan monomer: Synthesis and biological evaluation of immunomodulatory properties

Ribić

Habjanec

Brgles

et al. 2009

Bioorganic & Medicinal Chemistry

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“…The introduction and/or removal of protecting groups represent some of the most challenging transformations in sugar chemistry. In our previous work we described the synthesis and the hydrolysis of several series of acylated monosaccharides, acyl being acetyl, pivaloyl or a combination of both (Ljevaković et al, 1992;Tomić et al, 1993;Ljevaković et al, 1995;Petrović et al, 1997). Selective acylations and deacylations can be achieved with enzymes as regio-and chemoselective catalysts.…”

Section: Commentmentioning

confidence: 99%

“…Selective acylations and deacylations can be achieved with enzymes as regio-and chemoselective catalysts. We demonstrated that mammalian sera, which are a rich source of different enzymes, contain esterases specific for acylated monosaccharides and can be used for the selective hydrolysis of O-acyl derivatives of different monosaccharides (Tomić et al, 1993;Ljevaković et al, 1995;Petrović et al, 1997).…”

Section: Commentmentioning

confidence: 99%