Synthesis and 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside

Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275, Otter, Albin, Fu, Wenyi and Hindsgaul, Ole (1995) Synthesis and 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside. Carbohydrate Research, 276 (2). pp. 347-363. ISSN 0008-6215

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Abstract

All six isomeric mono-O-sulfates of β-d-Galp-(1 → 4)-β-d-GlcpNAc-O-(CH2)8COOMe (LacNAc-MCO) have been chemically synthesized and characterized by high resolution 1H NMR spectroscopy. Sulfation causes characteristic substitution-site-specific downfield shifts of 1H NMR signals. The 4C1 chair conformation of both pyranose residues of LacNAc are unaffected by mono-O-sulfation, and, with the exception of the 3-O-sulfate derivative, glycosidic torsion angles are also unaffected.

Item Type:	Article
Additional Information:	Funding Information: We thank Dr M.-H. Du, Mr F. Schweizer, and Dr F. Barresi for invaluable discussions. Dr O.P. Srivastava of the Alberta Research Council kindly provided 4,6-O-benzylidene-~-o-GlcpNAc-MCOTh. is work was supported by the Natural Sciences and Engineering Research Council of Canada.
Uncontrolled Keywords:	h nmr,n-acetyllactosamine,sulfated oligosaccharides,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	11 Sep 2024 14:30
Last Modified:	25 Sep 2024 18:09
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96718
DOI:	10.1016/0008-6215(95)00235-L

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