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Synthesis of Cluster Mannosides Carrying a Photolabile Diazirine Group
Author(s) -
Walter Mark,
Wiegand Michaela,
Lindhorst Thisbe K.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500692
Subject(s) - chemistry , diazirine , convergent synthesis , fimbria , stereochemistry , mannose , glycan , escherichia coli , glycoprotein , biochemistry , gene
We are investigating the mechanisms underlying the carbohydrate‐specific adhesion of bacteria such as Escherichia coli to the glycocalyx of their potential host cells. E. coli possess protein appendages, which are called type 1 fimbriae. Part of type 1 fimbriae is a protein named FimH, which is a mannose‐specific lectin. We wish to use photoaffinity labeling to elucidate mannose binding sites on FimH. Thus we report the synthesis of di‐ and trivalent cluster mannosides, which carry a photolabile diazirine group. The diazirine group was introduced by a convergent approach using thiourea bridging (products 6 , 13 , 17 , and 27 ) or in a divergent synthesis leading to the divalent cluster mannoside 31 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)