Stereoselective Chemical Synthesis of Sugar Nucleotides Via Direct Displacement of Acylated Glycosyl Bromides
Overview
Chemistry
Authors
Affiliations
[structure: see text]. The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.
Metabolic labeling of the bacterial peptidoglycan by functionalized glucosamine.
Xu Y, Hernandez-Rocamora V, Lorent J, Cox R, Wang X, Bao X iScience. 2022; 25(8):104753.
PMID: 35942089 PMC: 9356107. DOI: 10.1016/j.isci.2022.104753.
Synthesis and Applications of Carbohydrate-Based Organocatalysts.
Wojaczynska E, Steppeler F, Iwan D, Scherrmann M, Marra A Molecules. 2021; 26(23).
PMID: 34885873 PMC: 8659088. DOI: 10.3390/molecules26237291.
Metabolic Engineering of for Production of UDP-N-Acetylglucosamine.
Gauttam R, Desiderato C, Rados D, Link H, Seibold G, Eikmanns B Front Bioeng Biotechnol. 2021; 9:748510.
PMID: 34631687 PMC: 8495162. DOI: 10.3389/fbioe.2021.748510.
Papasavva A, Shegani A, Kiritsis C, Roupa I, Ischyropoulou M, Makrypidi K Molecules. 2021; 26(16).
PMID: 34443384 PMC: 8400719. DOI: 10.3390/molecules26164797.
Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment.
Tomioka T, Takahashi Y, Maejima T, Yabe Y, Iwata H, Hamann M Tetrahedron Lett. 2013; 54(48).
PMID: 24376284 PMC: 3873160. DOI: 10.1016/j.tetlet.2013.09.104.