Year: 2023
Type: article
Abstract: A combination of DFT calculations and experiments is used to describe how the selection of a promoter can control the stereochemical outcome of glycosylation reactions with the deoxy sugar saccharosamine. Depending on the promoter, either α- or β-linked reactive intermediates are formed. These studies show that differential modes of activation lead to the formation of distinct intermediates that undergo highly selective reactions through an S N 2-like mechanism.
Source: Organic Letters
Authors: Brian P. Garreffi, Ryan W. Kwok, Mateusz Marianski, Clay S. Bennett
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G2864586160, G3760170871, Hopping Sugars: molecular mechanism of protonatedglycans rearrangement, G5642286330, Nanoscience Connected to Life: An Interdisciplinary Traineeship Program in Bioinspired Nanotechnology, Glycosyl Sulfonates for the Construction of Difficult Glycosidic Linkages, Toward a Better Understanding of Factors Controlling Selectivity in Deoxy Sugar Oligosaccharide Synthesis
OpenAlex ID: W4389435279