Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3696-3702

  Qiao, Yan ^a   Lindner, Buko ^b   Zähringer, Ulrich ^b   Truog, Peter ^c   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b RESEARCH CENTER BORSTEL   (Germany)

^c LUNAMed AG   (Switzerland)

Author keywords

Glycophospholipids; Glycosidation; Gram positive bacteria; Lipoteichoic acid (LTA); Synthesis

Indexed keywords

ALANINE DERIVATIVE; DIACYLGLYCEROL DERIVATIVE; GALACTOSE; GLYCEROL; GLYCEROPHOSPHATE; GLYCOLIPID; HYDROXYL GROUP; LIPOTEICHOIC ACID;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; GLYCOSYLATION; NONHUMAN; PURIFICATION; SPECIES; STREPTOCOCCUS; SYNTHESIS;

BIOLOGICAL PRODUCTS; GALACTOSE; GLYCEROPHOSPHATES; GLYCOSYLATION; LIPOPOLYSACCHARIDES; STREPTOCOCCUS; TEICHOIC ACIDS;

EID: 77953156861     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.006     Document Type: Article

References (27)

1. Roethlisberger P., Iida-Tanaka N., Hollemeyer K., Heinzle E., Ishizuka I., and Fischer W. Eur. J. Biochem. 267 (2000) 5520
2. Roethlisberger, P. Ph. D Thesis, ETH Zurich, Switzerland, 1995.
3. Fischer W., Behr T., Hartmann R., Peter-Katalinić J., and Egge H. Eur. J. Biochem. 215 (1993) 851
4. Greenberg J.W., Fischer W., and Joiner K.A. Infect. Immun. 64 (1996) 3318
5. Fischer W. Microb. Drug. Resist. 3 (1997) 309
6. Pedersen C.M., Figueroa-Perez I., Lindner B., Ulmer A.J., Zähringer U., and Schmidt R.R. Angew. Chem., Int. Ed. 49 (2010) 2583
7. Umland O., Heine H., Miehe M., Marienfeld K., Staubach K.H., and Ulmer A.J. J. Leukocyte Biol. 75 (2004) 671
8. Morath S., Geyer A., and Hartung T. J. Exp. Med. 193 (2001) 393
9. Stadelmaier A., Morath S., Hartung T., and Schmidt R.R. Angew. Chem. 115 (2003) 945 Angew. Chem., Int. Ed. 2003, 42, 916
10. This compound is commercially available.
11. Figueroa-Perez I., Stadelmaier A., Morath S., Hartung T., and Schmidt R.R. Tetrahedron: Asymmetry 16 (2005) 493
12. Baeschlin D.K., Chaperon A.R., Charbonneau V., Green L.G., Ley S.V., Lücking U., and Walther E. Angew. Chem. 110 (1998) 3609 Angew. Chem., Int. Ed. 1998, 37, 3423
13. Wickberg B. Acta Chem. Scand. 12 (1958) 1187
14. Ferrières V., Bertho J.-N., and Plusquellec D. Carbohydr. Res. 311 (1998) 25
15. Ferrières V., Roussel M., Gelin M., and Plusquellec D. J. Carbohydr. Chem. 20 (2001) 855
16. Tsvetkov Y.E., and Nikolaev A.V. J. Chem. Soc., Perkin Trans. 1 (2000) 889
17. Choudhury A.K., and Roy N. Carbohydr. Res. 308 (1998) 207
18. Marlow A.K., and Kiessling L.L. Org. Lett. 3 (2001) 2517
19. Wang H., and Ning J. Carbohydr. Res. 338 (2003) 1033
20. Gandolfi-Donadĺo L., Gola G., de Lederkremer R.M., and Gallo-Rodriguez C. Carbohydr. Res. 341 (2006) 2487
21. Gallo-Rodriguez C., Gil-Libarona M.A., Mendoza V.M., and de Lederkremer R.M. Tetrahedron 38 (2002) 9373
22. Completo G.C., and Lowary T.L. J. Org. Chem. 73 (2008) 4513
23. Lee Y.J., Lee B.-Y., Jeon H.B., and Kim K.S. Org. Lett. 8 (2006) 3971
24. Bannwarth W., and Trzeciak A. Helv. Chim. Acta 70 (1987) 175
25. Kratzer B., and Schmidt R.R. Liebigs Ann. (1995) 957
26. Fischer W. Anal. Biochem. 194 (1991) 353
27. Strominger J.L., Park J.T., and Thompson R.E. J. Biol. Chem. 234 (1959) 3263