882516-56-5Relevant articles and documents
Synthesis of cluster mannosides carrying a photolabile diazirine group
Walter, Mark,Wiegand, Michaela,Lindhorst, Thisbe K.
, p. 719 - 728 (2007/10/03)
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, 2006.