Synthesis of an α-kojibiosyl substituted glycerol teichoic acid hexamer

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3668-3678

  Hogendorf, Wouter F J ^a   Bos, Leendert J Van den ^a   Overkleeft, Herman S ^a   Codée, Jeroen D C ^a   Marel, Gijsbert A Van der ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Carbohydrate; Glycosylation; Phosphoramidite; Teichoic acid

Indexed keywords

DISACCHARIDE; GLYCEROL; HYDROXYL GROUP; PHOSPHORAMIDOUS ACID; TEICHOIC ACID; THIOGLUCOSE; TRISACCHARIDE;

ARTICLE; CHEMISTRY; DEPROTECTION REACTION; ENTEROCOCCUS FAECALIS; NONHUMAN; SYNTHESIS;

DIMERIZATION; DISACCHARIDES; ENTEROCOCCUS FAECALIS; GLYCEROL; ORGANOPHOSPHORUS COMPOUNDS; TEICHOIC ACIDS;

ENTEROCOCCUS FAECALIS;

EID: 77953127081     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.03.071     Document Type: Article

References (36)

1. Weidenmaier C., and Peschel A. Nat. Rev. Microbiol. 6 (2008) 276
2. Neuhaus F.C., and Baddiley J. Microbiol. Mol. Rev. 67 (2003) 686
3. Fischer W. Adv. Microb. Physiol. 29 (1988) 233
4. Naumova I.B., Shashkov A.S., Tul'skaya E.M., Streshinskaya G.M., Kozlova Y.I., Potekhina N.V., Evtushenko L.I., and Stackebrandt E. FEMS Microbiol. Rev. 25 (2001) 269
5. Nikolaev A.V., Botvinko I.V., and Ross A.J. Carbohydr. Res. 342 (2007) 297
6. Wicken A.J., and Knox K.W. Science 187 (1975) 1161
7. Morath S., Stadelmaier A., Geyer A., Schmidt R.R., and Hartung T. J. Exp. Med. 195 (2002) 1635
8. Stadelmaier A., Morath S., Hartung T., and Schmidt R.R. Angew. Chem., Int. Ed. 42 (2003) 916
9. Deininger S., Stadelmaier A., von Aulock S., Morath S., Schmidt R.R., and Hartung T. J. Immun. 170 (2003) 4134
10. Morath S., von Aulock S., and Hartung T. J. Endotoxin Res. 6 (2005) 348
11. Figueroa-Perez I., Stadelmaier A., Morath S., Hartung T., and Schmidt R.R. Tetrahedron: Asymmetry 16 (2005) 493
12. Figueroa-Perez I., Stadelmaier A., Deininger S., von Aulock S., Hartung T., and Schmidt R.R. Carbohydr. Res. 341 (2006) 2901
13. Stadelmaier A., Figueroa-Perez I., Deininger S., von Aulock S., Hartung T., and Schmidt R.R. Bioorg. Med. Chem. 14 (2006) 6239
14. Theilacker C., Kaczynski Z., Kropec A., Fabretti F., Sange T., Holst O., and Huebner J. Infect. Immun. 74 (2006) 5703
15. Wang Y., Huebner J., Tzianabos A.O., Martirosian G., Kasper D.L., and Pier G.B. Carbohydr. Res. 316 (1999) 155
16. Huebner J., Wang Y., Krueger W.A., Madoff L.C., Martirosian G., Boisot S., Goldmann D.A., Kasper D.L., Tzianabos A.O., and Pier G.B. Infect. Immun. 67 (1999) 1213
17. Westerduin P., Veeneman G.H., Pennings Y., van der Marel G.A., and van Boom J.H. Tetrahedron Lett. 28 (1987) 1557
18. Elie C.J.J., Muntendam H.J., van den Elst H., van der Marel G.A., Hoogerhout P., and van Boom J.H. Rec. Trav. Chim. Pays-Bas 108 (1989) 219
19. Veeneman G.H., Brugghe H.F., van den Elst H., and van Boom J.H. Carbohydr. Res. 195 (1990) C1
20. Beaucage S.L., and Iyer R.P. Tetrahedron 48 (1992) 2223
21. Smith M., Rammler D.H., Goldberg I.H., and Khorana H.G. J. Am. Chem. Soc. 84 (1962) 430
22. van Boeckel C.A.A., Visser G.M., and van Boom J.H. Tetrahedron 41 (1985) 4557
23. Oltvoort J.J., van Boeckel C.A.A., De koning J.H., and van Boom J.H. Synthesis (1981) 305
24. Kim J.-H., Yang H., Park J., and Boons G.-J. J. Am. Chem. Soc. 127 (2005) 2357
25. Kim J.-H., Yang H., and Boons G.-J. Angew. Chem., Int. Ed. 44 (2005) 947
26. Kim J.-H., Yang H., Khot V., Whitfield D., and Boons G.-J. Eur. J. Org. Chem. (2006) 5007
27. Lemieux R.U., Hendriks K.B., Stick R.V., and James K. J. Am. Chem. Soc. 97 (1975) 4056
28. van Boeckel C.A.A., and van Boom J.H. Chem. Lett. (1981) 581
29. Adinolfi M., Iadonisi A., and Schiattarella M. Tetrahedron Lett. 44 (2003) 6479
30. Crich D., de la Mora M., and Vinod A.U. J. Org. Chem. 68 (2003) 8142
31. Codée J.D.C., Stubba B., Schiattarella M., Overkleeft H.S., van Boeckel C.A.A., van Boom J.H., and van der Marel G.A. J. Am. Chem. Soc. 127 (2005) 3767
32. Codée J.D.C., Litjens R.E.J.N., den Heeten R., Overkleeft H.S., van Boom J.H., and van der Marel G.A. Org. Lett. 5 (2003) 1519
33. Fukase K., Hashida M., and Kusumoto S. Tetrahedron Lett. 32 (1991) 3557
34. Zheng W., DeMattei J.A., Wu J.-P., Duan J.J.-W., Cook L.R., Oinuma H., and Kishi Y. J. Am. Chem. Soc. 118 (1996) 7946
35. 1H NMR analysis of the resulting mixture of pseudodisaccharides revealed an α/β ratio of ∼6/1, based on H-1 integrals.
36. Chipowsky S., and Lee Y.C. Carbohydr. Res. 31 (1973) 339