Synthesis of neoglycoproteins containing 5-O-phosphorylated Kdomonosaccharide, 4-O- and 5-O-phosphorylated α-Kdo→(2 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl disaccharide residues

Journal of Endotoxin Research

Volumn 3, Issue 2, 1996, Pages 151-164

  Sekljic, Harald ^a   Kosma, Paul ^a   Bartek, Johannes ^a   Fukase, Koichi ^b   Kusumoto, Shoichi ^b   Brade, Helmut ^c  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b OSAKA UNIVERSITY   (Japan)

^c RESEARCH CENTER BORSTEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINAE; HAEMOPHILUS INFLUENZAE;

3 (2 AMINOETHYLTHIO)PROPYL 3 DEOXY ALPHA MANNO 2 OCTULOPYRANOSIDONIC ACID 5 AMMONIUM HYDROGEN PHOSPHATE; 3 (2 AMINOETHYLTHIO)PROPYL 3 DEOXY BETA MANNO 2 OCTULOPYRANOSIDONIC ACID 5 AMMONIUM HYDROGEN PHOSPHATE; GLYCOPROTEIN; MERCAPTAMINE; MONOCLONAL ANTIBODY; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANTIBODY DETECTION; ARTICLE; CARBOHYDRATE METABOLISM; HAEMOPHILUS INFLUENZAE TYPE A; HYDROLYSIS; LIGAND BINDING; MUCOSA; NONHUMAN; PHOSPHATE TRANSPORT; PROTEIN PHOSPHORYLATION; PROTEIN SYNTHESIS;

EID: 0030013377     PISSN: 09680519     EISSN: None     Source Type: Journal    
DOI: 10.1177/096805199600300208     Document Type: Article

References (28)

1. Kilian M., Biberstein E.L. Genus III. Haemophilus. In: Krieg N.R. (Ed) Bergeys Manual of Systematic Bacteriology vol 1. Baltimore: Williams & Wilkins, 1984; 558.
2. Zamze S.E., Ferguson M.A.J., Moxon E.R. et al. Identification of phosphorylated 3-deoxy-manno-octulosonic acid as a component of Haemophilus influenzae lipopolysaccharide. Biochem J 1995; 245: 583-587.
3. +: description of a novel deep-rough chemotype. Eur J Biochem 1988; 177: 483-492.
4. Chaby R., Szabo L. 3-Deoxy-2-octulosonic acid 5-phosphate: a component of the endotoxin of Bordetella pertussis. Eur J Biochem 1975; 59: 277-280.
5. Brade H. Occurrence of 2-keto-3-deoxyoctonic acid 5-phosphate in lipopolysaccharides of Vibrio cholerae Ogawa and Inaba. J Bacteriol 1995; 161: 795-798.
6. Kondo S., Haishima Y., Hisatsune K. Analysis of the 2-keto-3-deoxyoctonate (Kdo) region of lipopolysaccharides isolated from non-O1 Vibrio cholerae O5R. FEMS Microbiol Lett 1990; 68: 155-158.
7. Kondo S., Haishima Y., Hisatsune K. Chemical structure of the 2-keto-3-deoxyoctonate (Kdo) region of the lipopolysaccharide isolated from O1 Vibrio cholerae NIH 41R (Ogawa). Microbiol Immunol 1991; 35: 675-680.
8. Kondo S., Zähringer U., Seydel U. et al. Chemical structure of the carbohydrate backbone of Vibrio parahaemolyticus serotype O12 lipopolysaccharide. Eur J Biochem 1991; 200: 689-698.
9. Kondo S., Haishima Y., Hisatsune K. Taxonomic implication of the apparent undetectability of 3-deoxy-D-manno-2-octulosonate (Kdo) in lipopolysaccharides of representatives of the family Vibrionaceae and the occurrence of Kdo 4-phosphate in their inner core regions. Carbohydr Res 1992; 231: 55-64.
10. Kumada H., Haishima Y., Kondo S. et al. Occurrence of 2-keto-3-deoxyoctonate (Kdo) and Kdo phosphate in lipopolysaccharides of Bacteroides species. Curr Microbiol 1993; 26: 239-244.
11. Kumada H., Kondo S., Umemoto T. Chemical structure of the 2-keto-3-deoxyoctonate region of lipopolysaccharide isolated from Bacteroides gingivalis. FEMS Microbiol Lett 1993; 108: 75-80.
12. Stütz P., Unger F. Chemical synthesis of core structures. In: Morrison D.C., Ryan J.L. (Eds) Bacterial Endotoxic Lipopolysaccharides, vol 1. Molecular Biochemistry and Cellular Biology. Boca Raton: CRC Press, 1992; 171-204 and references cited therein.
13. Sarfati S., Le Dur A., Szabó L. Phosphorylated sugars. Part 24. Methyl 3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid 4-(dihydrogen phosphate): synthesis, stability in acidic medium, and colorimetric estimation. J Chem Soc Perkin Trans I, 1988: 707-709.
14. Auzanneau F.I., Charon D., Szabó L. Phosphorylated sugars. Part 26. Synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid 7-phosphate. J Chem Soc Perkin Trans I 1990: 2831-2834.
15. Auzanneau F.I., Charon D., Szabó L. Phosphorylated sugars. Part 27. Synthesis and reactions, in acid medium, of 5-O-substituted methyl 3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid 4-phosphates. J Chem Soc Perkin Trans I 1991: 509-517.
16. Fukase K., Kamikawa T., Iwai Y. et al. Synthesis of allyl 3-deoxy-D-manno-2-octulopyranosidic acid 4-and 5-phosphates. Bull Chem Soc Jpn 1991; 64: 3267-3273.
17. Kosma P., Strobl M., März L. et al. Synthesis and immunoreactivity of poly(acrylamide) copolymers containing C-3-and C-7-modified, carboxyl-reduced, 4-O- and 5-O-phosphorylated Kdo residues. Carbohydr Res 1993; 238: 93-107.
18. Lee R.T., Lee Y.C. Synthesis of 3-(2-aminoethylthio)propyl glycosides. Carbohydr Res 1974; 37: 193-201.
19. Roy R., Laferrière C.A. Michael addition as the key step in the syntheses of sialyloligosaccharide-protein conjugates from N-acryloylated glycopyranosylamines. J Chem Soc Chem Commun 1990: 1709-1711.
20. Paulsen H., Wulff A., Brenken M. Preparation of synthetic antigens of the inner core region of lipopolysaccharides by copolymerization with acrylamide. Liebigs Ann Chem 1991: 1127-1145.
21. Holst O., Brade L., Kosma P. et al. Structure, serological specificity and synthesis of artificial glycoconjugates representing the genus-specific lipopolysaccharide epitope of Chlamydia spp. J Bacteriol 1991; 173: 1862-1866.
22. Kosma P., Gass J., Schulz G. et al. Artificial antigens. Synthesis of polyacrylamide copolymers containing 3-deoxy-D-manno-2-octulopyranosylonic acid (Kdo) residues. Carbohydr Res 1987; 167: 39-54.
23. Hofinger A, PhD Thesis, University of Agriculture, Vienna, 1991
24. Bannwarth W., Trzeciak A. A simple and effective chemical phosphorylation procedure for biomolecules. Helv Chim Acta 1987; 70: 175-186.
25. Kosma P., Bahnmüller R., Schulz G. et al. Synthesis of a tetrasaccharide of the genus-specific lipopolysaccharide epitope of Chlamydia. Carbohydr Res 1990; 208: 37-50.
26. Uhlmann E., Engels J. Chemical 5′-phosphorylation of oligonucleotides valuable in automated DNA synthesis. Tetrahedron Lett 1986; 27: 1023-1026.
27. Auzanneau F., Charon D., Szabó L. et al. Synthesis of 1,5-lactones of 3-deoxy-D-manno-2-octulopyranosonic acid (Kdo). Carbohydr Res 1988; 179: 125-136.
28. Lowry O.H., Roberts N., Leiner K.I. et al. The quantitative histochemistry of brain. I. Chemical methods. J Biol Chem 1954; 207: 1-17.