Chemical Synthesis of Lipoteichoic Acid and Derivatives

Microbial Glycobiology

Volumn , Issue , 2010, Pages 455-476

  Pedersen, Christian Marcus ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882838976     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374546-0.00025-0     Document Type: Chapter

References (42)

1. Baddiley, J., 1979. Polymers containing phosphorus in bacterial cell walls. In: Stec, W.J. (Ed.), Lectures Presented at the International Symposium on Phosphorus Chemistry Directed Towards Biology, Burzenin, Poland, 25-28 September 1979. Pergamon, Oxford, pp. 1-7.
2. Baeschlin D.K., Chaperon A.K., Charbonneau V., et al. Rapid assembly of oligosaccharides: total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Angew. Chem. Int. Ed. Engl. 1998, 37:3423-3428.
3. Deininger S., Stadelmaier A., von Aulock S., Morath S., Schmidt R.R., Hartung T. Definition of structural prerequisites for lipoteichoic acid-inducible cytokine induction by synthetic derivatives. J. Immunol. 2003, 170:4134-4138.
4. Deininger S., Figueroa-Perez I., Sigel S., et al. Definition of the cytokine inducing minimal structure of lipoteichoic acid using synthetic derivatives. Clin. Vaccine Immunol. 2007, 14:1629-1633.
5. Figueroa-Perez, I., 2007. Synthesis of fragments and one analogue of S. aureus LTA: investigations toward the synthesis of S. pneumoniae LTA. PhD thesis, University of Konstanz, Germany.
6. Figueroa-Perez I., Stadelmaier A., Morath S., Hartung T., Schmidt R.R. Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA). Tetrahedron Assym. 2005, 16:493-506.
7. Figueroa-Perez I., Stadelmaier A., Deininger S., von Aulock S., Hartung T., Schmidt R.R. Synthesis of Staphylococcus aureus lipoteichoic acid derivatives for determining the minimal structural requirements for cytokine induction. Carbohydr. Res. 2006, 341:2901-2911.
8. Fischer W. Glycerophosphoglycolipids presumptive biosynthetic precursors of lipoteichoic acids. Chemistry and Biological Activities of Bacterial Surface Amphiphiles 1981, 209-228. Academic Press, New York. G.D. Shockman, A.J. Wicken (Eds.).
9. Fischer W. Bacterial phosphoglycolipids and lipoteichoic acids. Handbook of Lipid Research 1990, Vol. 6:123-234. Plenum Press, New York. M. Kates (Ed.).
10. Fischer W. Lipoteichoic acid and lipids in the membrane of Staphylococcus aureus. Med. Microbiol. Immunol. 1994, 183:61-76.
11. Fischer W. Lipoteichoic acids and lipoglycans. Bacterial Cell Wall. 1994, 199-215. Elsevier, Amsterdam. J.-M. Ghuysen (Ed.).
12. Fischer W., Koch U. Alanine ester substitution and its effect on the biological properties of lipoteichoic acids. Chemistry and Biological Activities of Bacterial Surface Amphiphiles 1981, 181-194. Academic Press, New York. G.D. Shockman, A.J. Wicken (Eds.).
13. Fischer W., Koch H.U., Rösel P., Fiedler F., Schmuk L. Structural requirements of lipoteichoic acid carrier for recognition by the poly(ribitol phosphate) polymerase from Staphylococcus aureus H. A study of various lipoteichoic acids, derivatives, and related compounds. J. Biol. Chem. 1980, 225:4457-4562.
14. Fukase K., Tanaka H., Torii S., Kusumoto S. 4-Nitrobenzyl group for protection of hydroxyl functions. Tetrahedron Lett. 1990, 31:389-392.
15. Fukase K., Matsumoto T., Ito N., Yoshimura T., Kotani S., Kusumoto S. Synthetic study on lipoteichoic acid of gram positive bacteria. I. Synthesis of proposed fundamental structure of Streptococcus pyogenes lipoteichoic acid. Biological role of synthetic LTA. Bull. Chem. Soc. Jpn. 1992, 65:2643-2654.
16. Fukase K., Yoshimura T., Kotani S., Kusumoto S. Synthetic study of lipoteichoic acid of gram positive bacteria. II. Synthesis of the proposed fundamental structure of Enterococcus hirae lipoteichoic acid. Bull. Chem. Soc. Jpn. 1994, 67:473-482.
17. Greenberg J.W., Fischer W., Joiner K.A. Influence of lipoteichoic acid structure on recognition by macrophage scavenger receptor. Infect. Immunol. 1996, 64:3318-3325.
18. Grundler G., Schmidt R.R. Anwendung des Trichloracetimidat-Verfahrens auf 2-Azidoglucose- und 2-Azidogalactose-Derivate. Liebigs Ann. Chem. 1984, 1826-1847.
19. Hashimato S., Hayashi M., Noyori R. Glycosylation using glucopyranosyl fluorides and silicon-based catalysts. Solvent dependency of the stereoselection. Tetrahedron Lett. 1984, 25:1379-1382.
20. Lok C.M., Ward J-P., van Dorp D.A. The synthesis of chiral glycerides starting from d- and l-serine. Chem. Phys. Lipids 1976, 16:115-122.
21. 4 for activation of glycosyl fluorides and application to highly β-selective gylcosidation of d-mycinose. Tetrahedron Lett. 1988, 29:3567-3570.
22. Morath S., Geyer A., Hartung T. Structure-function relationship of cytokine induction by lipoteichoic acid from Staphylococcus aureus. J. Exp. Med. 2001, 193:393-397.
23. Morath S., Stadelmaier A., Geyer A., Schmidt R.R., Hartung T. Synthetic lipoteichoic acid from Staphylococcus aureus is a potent stimulus of cytokine release. J. Exp. Med. 2002, 195:1635-1640.
24. Morath S., von Aulock S., Hartung T. Structure/function relationships of lipoteichoic acids. J. Endotoxin Res. 2005, 11:348-356.
25. Mukaiyama T., Murai Y., Shoda S. An efficient method for glucosylation of hydroxy compounds using glucopyranosyl fluoride. Chem. Lett. 1981, 431-432.
26. Nashed M.A., Anderson L. Iodine as a reagent for the ready hydrolysis of prop-1-enyl glycosides, or their conversion into oxazolines. J. Chem. Soc. Chem. Commun. 1982, 18:1274-1276. and references.
27. Oltvoort J.J., van Boeckel C.A.A., de Koning J.H., van Boom J.H. Use of the cationic iridium complex 1,5-cyclooctadiene-bis[methyldiphenylphosphine]-iridium hexafluorophosphate in carbohydrate chemistry: smooth isomerization of allyl ethers to 1-propenyl ethers. Synthesis 1981, 305-308.
28. Oltvoort J.J., van Boeckel C.A.A., de Koning J.H., van Boom J.H. A simple approach to the synthesis of membrane teichoic acid fragment of Staphylococcus aureus. Recl. Trav. Chim. Pays-Bas 1982, 101:87-91.
29. Oltvoort J.J., Kloosterman M., van Boeckel C.A.A., van Boom J.H. Synthesis of a lipoteichoic acid-carrier fragment of Staphylococcus aureus. Carbohydr. Res. 1984, 130:147-163.
30. Reese C.B., Tau L. Reaction between 4-nitrobenzaldoximate ion and phosphotriesters. Tetrahedron Lett. 1978, 19:4443-4446.
31. Reese C.B., Titmas R.C., Yau L. Oximate ion promoted unblocking of oligonucleotide phosphotriester intermediates. Tetrahedron Lett. 1978, 19:2727-2730.
32. Schmidt R.R., Moering U., Reichrath M. Synthesis of α- and β-glycopyranosides via 1-O-alkylation. Tetrahedron Lett. 1980, 21:3565-3568.
33. Smid P., de Zwart M., Jörning W.P.A., van der Marel G.A., van Boom J.H. Stereoselective synthesis of a tetrameric fragment of Streptococcus pneumoniae type 1 containing an α-linked 2-acetamido-4-amino-2,4,6-trideoxy-d-galactopyr-anose (SUGp) unit. J. Carbohydr. Chem. 1993, 12:1073-1090.
34. Stadelmaier A., Morath S., Hartung T., Schmidt R.R. Synthesis of the first fully active lipoteichoic acid. Angew. Chem. Int. Ed. Engl. 2003, 42:916-920.
35. Stadelmaier A., Figueroa-Perez I., Deininger S., von Aulock S., Hartung T., Schmidt R.R. A Staphy-lococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues. Bioorg. Med. Chem. 2006, 14:6239-6254.
36. Suda Y., Tochio H., Kawano K., et al. Cytokine-inducing glycolipids in the lipoteichoic acid fraction from Enterococcus Lirae ATCC 9790. FEMS Immunol. Microbiol 1995, 12:97-112.
37. Takada H., Kawabata Y., Arakaki R., et al. Molecular and structural requirements of a lipoteichoic acid from Enterococcus hirae ATCC 9790 for cytokine-inducing, antitumor, and antigenic activities. Infect. Immun. 1996, 63:57-65.
38. Tsutsui O., Kokeguchib S., Matsumura T., Kato K. Relationship of the chemical structure and immunobiological activities of lipoteichoic acid from Streptococcus faecalis (Enterococcus hirae) ATCC 9790. FEMS Microbiol. Lett. 1991, 76:211-218.
39. van Boeckel C.A.A., van Boom J.H. Synthesis of Steptococci phosphatidyl-α-diglycosyldiglyceride and related glycolipids. Application of the tetraisopropyldisiloxane-1,3-diyl (TIPS) protecting group in sugar chemistry. Part V. Tetrahedron 1985, 41:4567-4575.
40. Veeneman G.H., Gomes L.J.F., van Boom J.H. Synthesis of fragments of a Streptococcus pneumoniae type-specific capsular polysaccharide. Tetrahedron 1989, 45:7433-7448.
41. Westphal O., Lüderitz O., Keiderling W. Effects of bacterial toxins; biochemical analysis of inflammation. Zentralbl. Bakteriol. Parasitenkd. Infectionskr. Hyg. 1952, 158:152-160.
42. Wickberg B. Synthesis of l-glyceritol-d-galactopyranosides. Acta Chem. Scand. 1958, 12:1187-1201.