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Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides.

A highly efficient one-pot methodology is described for the synthesis of heparin and heparan sulfate oligosaccharides utilizing thioglycosides with well-defined reactivity as building blocks. L-Idopyranosyl and D-glucopyranosyl thioglycosides 5 and 10 were used as donors due to low reactivity of uro... Full description

Journal Title: Journal of the American Chemical Society October 24, 2007, Vol.129(42), pp.12795-12800
Main Author: Polat, Tülay
Other Authors: Wong, Chi-Huey
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0002-7863
Link: http://search.proquest.com/docview/68401222/?pq-origsite=primo
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recordid: proquest68401222
title: Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides.
format: Article
creator:
  • Polat, Tülay
  • Wong, Chi-Huey
subjects:
  • Carbohydrate Sequence–Methods
  • Chemistry, Organic–Chemistry
  • Disaccharides–Chemistry
  • Glycosylation–Chemistry
  • Heparin–Chemistry
  • Hexoses–Chemistry
  • Hydrogen–Chemistry
  • Models, Chemical–Chemistry
  • Molecular Sequence Data–Chemistry
  • Oligosaccharides–Chemistry
  • Oxygen–Chemistry
  • Polysaccharides–Chemistry
  • Pyrans–Chemistry
  • Uronic Acids–Chemistry
  • Disaccharides
  • Hexoses
  • Oligosaccharides
  • Polysaccharides
  • Pyrans
  • Uronic Acids
ispartof: Journal of the American Chemical Society, October 24, 2007, Vol.129(42), pp.12795-12800
description: A highly efficient one-pot methodology is described for the synthesis of heparin and heparan sulfate oligosaccharides utilizing thioglycosides with well-defined reactivity as building blocks. L-Idopyranosyl and D-glucopyranosyl thioglycosides 5 and 10 were used as donors due to low reactivity of uronic acids as the glycosyl donors in the one-pot synthesis. The formation of uronic acids by a selective oxidation at C-6 was performed after assembly of the oligosaccharides. The efficiency of this programmable strategy with the flexibility for sulfate incorporation was demonstrated in the representative synthesis of disaccharides 17, 18, tetrasaccharide 23, and pentasaccharide 26.
language: eng
source:
identifier: ISSN: 0002-7863
fulltext: fulltext
issn:
  • 00027863
  • 0002-7863
url: Link


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titleAnomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides.
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identifierISSN: 0002-7863
subjectCarbohydrate Sequence–Methods ; Chemistry, Organic–Chemistry ; Disaccharides–Chemistry ; Glycosylation–Chemistry ; Heparin–Chemistry ; Hexoses–Chemistry ; Hydrogen–Chemistry ; Models, Chemical–Chemistry ; Molecular Sequence Data–Chemistry ; Oligosaccharides–Chemistry ; Oxygen–Chemistry ; Polysaccharides–Chemistry ; Pyrans–Chemistry ; Uronic Acids–Chemistry ; Disaccharides ; Hexoses ; Oligosaccharides ; Polysaccharides ; Pyrans ; Uronic Acids
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descriptionA highly efficient one-pot methodology is described for the synthesis of heparin and heparan sulfate oligosaccharides utilizing thioglycosides with well-defined reactivity as building blocks. L-Idopyranosyl and D-glucopyranosyl thioglycosides 5 and 10 were used as donors due to low reactivity of uronic acids as the glycosyl donors in the one-pot synthesis. The formation of uronic acids by a selective oxidation at C-6 was performed after assembly of the oligosaccharides. The efficiency of this programmable strategy with the flexibility for sulfate incorporation was demonstrated in the representative synthesis of disaccharides 17, 18, tetrasaccharide 23, and pentasaccharide 26.
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