Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(6): 952-958
DOI: 10.1055/s-2006-926358
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
Further Information
Received
31 August 2005
Publication Date:
27 February 2006 (online)
Publication History
Publication Date:
27 February 2006 (online)
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
-
1a
Klemm P. Eur. J. Biochem. 1984, 143: 395 -
1b
Klemm P. Rev. Infect. Dis. 1985, 7: 321 -
1c
Karlsson KA. Curr. Opin. Struct. Biol. 1995, 5: 622 -
2a
Foxman B.Zhang L.Palin K.Tallman P.Marrs CF. J. Infect. Dis. 1995, 171: 1514 -
2b
Connell H.Agace W.Klemm P.Schembri M.Maarild S.Svanborg C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93: 9827 -
2c
Sukurenko EV.Courtney HS.Ohmann DE.Klemm P.Hasty LD. J. Bacteriol. 1994, 176: 748 -
2d
Mulvey MA.Lopez-Boado YS.Wilson CL.Roth R.Parks WC.Heuser J.Hultgren SJ. Science 1998, 282: 1494 - 3
Vetsch M.Puorger C.Spirig T.Grauschopf U.Weber-Ban E.-U.Glockshuber R. Nature 2004, 431: 330 -
4a
Choudhury D.Thompson A.Stojanoff V.Langermann S.Pickner J.Hultgren SJ.Knight SD. Science 1999, 285: 1061 -
4b
Hung CS.Bouckaert J.Hung D.Pinkner J.Widberg C.DeFusco A.Auguste CG.Strouse R.Langermann S.Waksman G.Hultgren SJ. Mol. Microbiol. 2002, 44: 903 -
4c
Bouckaert J.Berglund J.Schembri M.Genst ED.Cools L.Wuhrer M.Hung C.-S.Pinkner J.Slättegård R.Zavialov A.Choudhury D.Langermann S.Hultgren SJ.Wyns L.Klemm P.Oscarson S.Knight SD.Greve HD. Mol. Microbiol. 2005, 55: 441 -
5a
Firon N.Ofek I.Sharon N. Carbohydr. Res. 1983, 120: 235 -
5b
Lindhorst ThK.Kieburg C.Krallmann-Wenzel U. Glycoconj. J. 1998, 15: 605 -
5c
Nagahori N.Lee RT.Nishimura S.-I.Pagé D.Roy R.Lee YC. ChemBioChem 2002, 3: 836 -
6a
Sauer FG.Barnhart M.Choudhury D.Knight G.Wacksmann SD.Hultgren SJ. Curr. Opin. Struc. Biol. 2000, 5: 548 -
6b
Knight SD.Berglund J.Choudhury D. Curr. Opin. Chem. Biol. 2000, 6: 653 -
7a
Fleming SA. Tetrahedron 1995, 51: 12479 -
7b
Hatanaka Y.Nakayama H.Kanaoka Y. Rev. Heteroat. Chem. 1996, 14: 213 - 8
Sharon N. FEBS Lett. 1987, 217: 145 -
9a
Lindhorst TK.Kieburg C. Angew. Chem., Int. Ed. Engl. 1996, 35: 1953 ; Angew. Chem. 1996, 108, 2083 -
9b
Saitz-Barria1 C.Torres-Pinedo A.Santoyo-González F. Synlett 1999, 1891 -
9c
Dam TK.Roy R.Pagé D.Brewer CF. Biochemistry 2002, 41: 1351 -
9d
Gómez-Garcíá M.Benito JM.Rodríguez-Lucena D.Yu J.-X.Chmurski K.Ortiz Mellet C.Gutiérrez Gallego R.Maestre A.Defaye J.García Fernández JM. J. Am. Chem. Soc. 2005, 127: 7970 - 10
Ponnusamy E.Fotadar U.Spisni A.Fiat D. Synthesis 1986, 48 - 11
Mancuso AJ.Huang SL.Swern D. J. Org. Chem. 1978, 43: 2480 -
12a
Church RFR.Weiss MJ. J. Org. Chem. 1970, 35: 2465 -
12b
Lehmann J.Weitzel UP. Carbohydr. Res. 1996, 294: 65 - 13
Lindhorst TK.Kieburg C. Synthesis 1995, 1228 - 14
Kötter S.Krallmann-Wenzel U.Ehlers S.Lindhorst TK. J. Chem. Soc., Perkin Trans. 1 1998, 2193 - 15
Zemplén G.Pascu E. Ber. Dtsch. Chem. Ges. 1929, 62: 1613 - 16
Benito JM.Ortiz Mellet C.Sadalapure K.Lindhorst TK.Defaye J.García Fernández JM. Carbohydr. Res. 1999, 320 : 37 -
17a
Kondo Y. Carbohydr. Res. 1986, 154: 305 -
17b
Wang P.Shen G.-J.Wang Y.-F.Ichikawa Y.Wong C.-H. J. Org. Chem. 1993, 58: 3985 - 18
Schönecker B.Ponsold K. J. Prakt. Chem. 1976, 318: 483 - 19
Walter M.Lindhorst TK. Monatsh. Chem./Chemical Monthly 2002, 133: 473 - 20
Soli ED.Manoso AS.Patterson MC.DeShong P. J. Org. Chem. 1999, 64: 3171 - 21
García Fernández JM.Ortiz Mellet C. Adv. Carbohydr. Chem. Biochem. 1999, 55: 35 - 22
Lehmann J.Ziser L. Carbohydr. Res. 1992, 225: 83