Kerstin Ekelöf

Stockholm University

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Stefan Oscarson

University College Dublin

Lars‐Inge Olsson

AstraZeneca (Sweden)

Per J. Garegg

Stockholm University

Karin Mannerstedt

Gubra (Denmark)

Cooperative Institutions

Stockholm University

Uppsala University

AstraZeneca (Sweden)

Duke University

Swedish Orphan Biovitrum (Sweden)

Gubra (Denmark)

Carlsberg Laboratory

Linköping University

Universidad de Sevilla

University of Konstanz

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Synthesis of 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6-tri-O-β-d-glucopyranosyl-α-d-glucopyranosyl)-α-d-manno-oct-2-ulopyranosidonic acid, a highly branched pentasaccharide corresponding to structures found in lipopolysaccharides from Moraxella catarrhalis

Carbohydrate Research (1995)

Kerstin Ekelöf Stefan Oscarson

Tetrasaccharide

Trifluoromethanesulfonate

Moiety

Glycosyl donor

Glycoconjugate

Derivative (finance)

Monosaccharide

Glycal

Sulfonium

10.1016/0008-6215(95)00269-3

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Citations (31)

Syntheses of 4- and/or 4′-Phosphate Derivatives of Methyl 3-O-l-Glycero-α-d-manno-heptopyranosyl-l-glyceroα-d-manno-heptopyranoside and Their 2-(4-Trifluoro-acetamidophenyl)ethyl Glycoside Analogues.

Journal of Carbohydrate Chemistry (1995)

Kerstin Ekelöf Stefan Oscarson

Abstract Syntheses are described of the three disaccharides: methyl 3-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside 4-phosphate, methyl 3-O-(L-glycero-α-D-manno-heptopyranosyl 4-phosphate)-L-glycero-α-D-manno-heptopyranoside, and methyl 3-O-(L-glycero-α-D-manno-heptopyranosyl 4-phosphate)-L-glycero-α-D-manno-heptopyranoside 4-phosphate together with their 2-(4-trifluoroacetamidophenyl)ethyl glycoside analogues. These correspond to phosphorylated structures found in the inner core region of lipopolysaccharides from Salmonella. The known derivative methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside was used as a common heptose precursor. Phosphorylation on suitably protected disaccharide derivatives was performed by treatment with phosphorus triimidazolate in dichloromethane followed by the addition of benzyl alcohol and in situ oxidation with m-chloroperbenzoic acid to give the dibenzyltriester phosphate derivatives, which after deprotection gave the target compounds.

Dichloromethane

Disaccharide

Derivative (finance)

10.1080/07328309508002073

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Citations (12)

Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of Moraxella catarrhalis

The Journal of Organic Chemistry (1996)

Kerstin Ekelöf Stefan Oscarson

The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the 6-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.

Trifluoromethanesulfonate

Glycosyl donor

Oligosaccharide

Sulfonium

Moiety

10.1021/jo960789p

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Citations (32)

ChemInform Abstract: Towards the 21^st Century: The Emerging Importance of Oligosaccharide Synthesis

ChemInform (1998)

Kerstin Ekelöf Per J. Garegg Lars‐Inge Olsson Stefan Oscarson

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Oligosaccharide

10.1002/chin.199804283

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Synthesis of oligosaccharides corresponding to lipopolysaccharide structures of Salmonell typhimurium and Moraxella catarrhalis

Kerstin Ekelöf

Synthesis of oligosaccharides corresponding to lipopolysaccharide structures of Salmonella typhimurium and Moraxella catarrhalis

Moraxella (Branhamella) catarrhalis

Source

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Evaluation of thioglycosides of Kdo as glycosyl donors