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Journal of Carbohydrate Chemistry Volume 20, 2001 - Issue 7-8
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Original Articles

SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUESCitation[1]

Andrej-Jakob Ott Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
,
Meinolf Brackhagen Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
,
Anahit Davtyan Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
,
Birte Nolting Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
,
Hanna Boye Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
,
Astrid Schoknecht Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, Germany
&
Christian Vogel Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstraβe 9, Rostock, 18055, GermanyCorrespondence[email protected]
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Pages 611-636 | Received 27 Feb 2001, Accepted 26 Apr 2001, Published online: 16 Aug 2006
 
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Abstract

Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2′-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

ACKNOWLEDGMENTS

The authors are indebted to the Deutschen Forschungsgemeinschaft as well as the Fonds der Chemischen Industrie for financial support.

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