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Synthesis 2006(6): 952-958  
DOI: 10.1055/s-2006-926358
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Modular System for the Preparation of Diazirine-Labeled Mannose Derivatives Using Thiourea Bridging

Mark Walter, Thisbe K. Lindhorst*
Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3, 24098 Kiel, Germany
Fax: +49(431)8807410; e-Mail: tklind@oc.uni-kiel.de;
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Publication History

Received 31 August 2005
Publication Date:
27 February 2006 (online)

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Abstract

The protein FimH is a bacterial lectin, which is utilized by Escherichia coli to adhere to the glycocalyx of potential host cells. FimH has specificity for α-mannosyl residues, as revealed by biological as well as X-ray studies. To further investigate the molecular details of carbohydrate binding to FimH, photolabile mannose derivatives are important tools to covalently mark carbohydrate binding sites on FimH. Here, a modular approach for the synthesis of photolabile diazirine-labeled mannosides and mannosyl clusters is reported. The convergent synthesis utilizes thiourea bridging of the amino-functionalized diazirine 4 with NCS-functionalized carbohydrates.

Key words

carbohydrates - glycoclusters - photolabeling - diazirines - thiourea