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Johnston BD, Pinto BM. Synthesis of 1,2- and 1,3-N-Linked Disaccharides of 5-Thio-alpha-D-mannopyranose as Potential Inhibitors of the Processing Mannosidase Class I and Mannosidase II Enzymes. J Org Chem. 1998;63(17):5797-5800doi: 10.1021/jo980168r.
Johnston, B. D., & Pinto, B. M. (1998). Synthesis of 1,2- and 1,3-N-Linked Disaccharides of 5-Thio-alpha-D-mannopyranose as Potential Inhibitors of the Processing Mannosidase Class I and Mannosidase II Enzymes. The Journal of organic chemistry, 63(17), 5797-5800. https://doi.org/10.1021/jo980168r
Johnston, Blair D., and Pinto, B. Mario. "Synthesis of 1,2- and 1,3-N-Linked Disaccharides of 5-Thio-alpha-D-mannopyranose as Potential Inhibitors of the Processing Mannosidase Class I and Mannosidase II Enzymes." The Journal of organic chemistry vol. 63,17 (1998): 5797-5800. doi: https://doi.org/10.1021/jo980168r
Johnston BD, Pinto BM. Synthesis of 1,2- and 1,3-N-Linked Disaccharides of 5-Thio-alpha-D-mannopyranose as Potential Inhibitors of the Processing Mannosidase Class I and Mannosidase II Enzymes. J Org Chem. 1998 Aug 21;63(17):5797-5800. doi: 10.1021/jo980168r. PMID: 11672179.
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J Org Chem. 1998 Aug 21;63(17):5797-5800. doi: 10.1021/jo980168r.

Synthesis of 1,2- and 1,3-N-Linked Disaccharides of 5-Thio-alpha-D-mannopyranose as Potential Inhibitors of the Processing Mannosidase Class I and Mannosidase II Enzymes.

The Journal of organic chemistry

Blair D. Johnston, B. Mario Pinto

Affiliations

  1. Department of Chemistry and Protein Engineering Network of Centres of Excellence, Simon Fraser University, Burnaby, B.C., Canada V5A 1S6.

PMID: 11672179 DOI: 10.1021/jo980168r

Abstract

The syntheses of S/N acetal heteroatom analogues of 1,2- and 1,3-linked mannopyranose disaccharides are described. The compounds are analogues of the Man-alpha-(1-->2)-Man and Man-alpha-(1-->3)-Man disaccharide components of oligosaccharides found in N-glycoproteins that are cleaved by trimming mannosidases during glycoprotein processing. Glycosylamine formation, without the necessity of hydroxyl group protection, proceeded through acid-catalyzed condensation reactions of 5-thio-D-mannose with either methyl 2-amino-2-deoxy- or 3-amino-3-deoxy-alpha-D-mannopyranoside to give methyl 2-amino-2-deoxy-2-N-(5-thio-alpha/beta-D-mannopyranosyl)-alpha-D-mannopyranoside (2) or methyl 3-amino-3-deoxy-3-N-(5-thio-alpha/beta-D-mannopyranosyl)-alpha-D-mannopyranoside (3), respectively. The superiority of mercuric chloride over acetic acid as a catalyst for this reaction is reported. Acetylation of the anomeric mixtures gave the heptaacetates from which the major beta'-isomers could be separated by chromatography and/or crystallization.

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