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

Robert A. Field; Albin Otter; Wenyi Fu; Ole Hindsgaul

doi:10.1016/0008-6215(95)00235-L

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

Robert A. Field, Albin Otter, Wenyi Fu, Ole Hindsgaul

School of Chemistry, Pharmacy and Pharmacology

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

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.

Original language	English
Pages (from-to)	347-363
Number of pages	17
Journal	Carbohydrate Research
Volume	276
Issue number	2
DOIs	https://doi.org/10.1016/0008-6215(95)00235-L
Publication status	Published - 23 Oct 1995

Keywords

H NMR
N-Acetyllactosamine
Sulfated oligosaccharides

Access to Document

10.1016/0008-6215(95)00235-L

Cite this

@article{22ca5e8d0d11487cae000f6adac9d506,

title = "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",

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.",

keywords = "H NMR, N-Acetyllactosamine, Sulfated oligosaccharides",

author = "Field, {Robert A.} and Albin Otter and Wenyi Fu and Ole Hindsgaul",

note = "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.",

year = "1995",

month = oct,

day = "23",

doi = "10.1016/0008-6215(95)00235-L",

language = "English",

volume = "276",

pages = "347--363",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "2",

}

TY - JOUR

T1 - 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

AU - Field, Robert A.

AU - Otter, Albin

AU - Fu, Wenyi

AU - Hindsgaul, Ole

N1 - 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.

PY - 1995/10/23

Y1 - 1995/10/23

N2 - 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.

AB - 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.

KW - H NMR

KW - N-Acetyllactosamine

KW - Sulfated oligosaccharides

UR - http://www.scopus.com/inward/record.url?scp=0028970834&partnerID=8YFLogxK

U2 - 10.1016/0008-6215(95)00235-L

DO - 10.1016/0008-6215(95)00235-L

M3 - Article

C2 - 8542605

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VL - 276

SP - 347

EP - 363

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 2

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