Celebrating the golden anniversary of the discovery of bacillosamine, the diamino sugar of a Bacillus

Glycobiology

Volumn 17, Issue 11, 2007, Pages 1150-1155

  Sharon, Nathan ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Bacillus licheniformis; Campylobacter jejuni; Fucosamine; Glycoproteins; Polysaccharide

Indexed keywords

2,4 DI N ACETYLBACILLOSAMINE; 4 N ACETYLBACILLOSAMINE; AMINOGLYCOSIDE DERIVATIVE; AMINOSUGAR; BACILLOSAMINE; BACTERIAL POLYSACCHARIDE; GLYCOPROTEIN; N ACETYLGLUCOSAMINE; UNCLASSIFIED DRUG;

ARTICLE; BACILLUS LICHENIFORMIS; BACILLUS SUBTILIS; BIOSYNTHESIS; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; DEGRADATION KINETICS; ION EXCHANGE CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

BACILLUS; CARBOHYDRATE SEQUENCE; HEXOSAMINES; HISTORY, 20TH CENTURY; POLYSACCHARIDES, BACTERIAL;

BACILLUS (BACTERIUM); BACILLUS LICHENIFORMIS; BACILLUS SUBTILIS; BACTERIA (MICROORGANISMS); CAMPYLOBACTER JEJUNI;

EID: 35348970382     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwm089     Document Type: Article

References (33)

1. Aas FE, Vik A, Vedde J, Koomey M, Egge-Jacobsen W. 2007. Neisseria gonorrhoeae O-linked pilin glycosylation: Functional analyses define both the biosynthetic pathway and glycan structure. Mol Microbiol. 65:607-624.
2. Amin MN, Ishivata A, Ito Y. 2006. Synthesis of asparagine-linked bacillosamine. Carbohydr Res. 341:1922-1929.
3. Bedini E, Esposito D, Parrilli M. 2006. A versatile strategy for the synthesis of N-acetylbacillosamine-containing disaccharide building blocks related to bacterial O-antigens. SYNLETT. 6:825-830.
4. Bundle DR, Josephson S. 1980. Chlorosulfation of amino-sugars - Synthesis of methyl 2-acetamido-4-amino-2,4,6-trideoxy,-beta-D-glucopyranoside. (bacillosamine) from a D-glucosamine derivative. Can J Chem. 58:2679-2685.
5. Creuzenet C. 2004. Characterization of CJ1293, a new UDP-GlcNAc C6 dehydratase from Campylobacter jejuni. FEBS Lett. 559:136-140.
6. Feldman MF, Wacker M, Hernandez M, Hitchen PG, Marolda CL, et al. 2005. Engineering N-linked protein glycosylation with diverse O antigen lipopolysaccharide structures in Escherichia coli. Proc Natl Acad Sci USA. 102:3016-3021.
7. Gardell S. 1953. Separation on Dowex 50 ion exchange resin of glucosamine and galactosamine and their quantitative determination. Acta Chimica Scand. 7:207-215.
8. Harel E, Sílbert JE, Sharon N. 1966. Chemical synthesis and characterization of thymidine diphosphate N acetyl-α-D-glucosamine and guanosine diphosphate N acetyl-α-D-glucosamine. Arch Biochem Biophys. 117:296-300.
9. Karlyshev AV, Everest P, Linton D, Cawthraw S, Newell DG, Wren BW. 2004. The Campylobacter jejuni general glycosylation system is important for attachment to human epithelial cells and in the colonization of chicks. Microbiology. 150:1957-1964.
10. Kenne L, Lindberg B, Petersson K, Katzenellenbogen E, Ronamowska E. 1980. Structural studies of the O-specific side-chains of the Shigella sonnei phase I lipopolysaccharide. Carbohydr Res. 78:119-126.
11. Lindberg B, Lindqvist B, Lonngren J, Powell DA. 1980. Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type I. Carbohydr Res. 78:111-117.
12. Liav A, Hildesheim J, Zehavi U, Sharon N. 1974. Synthesis of 2-acetamido-2,6-dideoxy-D-glucose (N-acetyl-D-quinovosanline), 2-acetamido-2,6-dideoxy-D-galactose (N-acetyl-D-fucosamine), and 2,4-diacetamido-2,4,6-trideoxy-D-glucose from 2-acetamido-2-deoxy-D-glucose. Carbohydr Res. 33: 217-227.
13. Liav A, Jacobson I, Sheinblaft M, Sharon N. 1976. Synthesis of 2,4-diacetamido-2,4,6-trideoxy-D-galactose. Carbohydr Res. 66:95-101.
14. Liav A, Sharon N. 1973. Synthesis of 2,4-diacetamido-2,4,6-trideoxy-L-altrose, -L-idose, and -L-talose from benzyl 6-deoxy-3,4,-O-isopropylidene-beta-L-galactopyranoside. Carbohydr Res. 30:109-126.
15. Liu X, McNally DJ, Nothaft H, Szymanski CM, Brisson JR, Li J. 2006. Mass spectrometry-based glycomics strategy for exploring N-linked glycosylation in eukaryotes and- bacteria. Anal Chem. 78:6081-6087.
16. Olivier N, Chen M, Behr JR, Imperiali B. 2OO7. In vitro biosynthesis of UDP-N,N -diacetylbacillosamine by enzymes of the Campylobacter jejuni general protein glycosylation pathway. Biochemistry. 45:13659-13669.
17. Rondle CJ, Morgan WT. 1955. The determination of glucosamine and galactosamine. Biochem J. 61:586-589.
18. Schäffer C, Scherf T, Christian R, Kosma P, Zayni S, Messner P,'Sharon N. 2001. Purification and structure elucidation o the N acetylbacillosamine-containing polysaccharide from Bacillus licheniformis ATCC 9945. Eur J Biochem. 268:857-864.
19. Schoenhofen IC, McNally DJ, Vinogradov E, Whitfield D, Young NM, et al. 2006. Functional characterization of dehydratase/aminotransferase pairs from Helicobacter and Campylobacter. Enzymes distinguishing the pseudaminic and and bacillosamine biosynthetic pathways. J Biol Chem. 281:723-732.
20. Sharon N. 1957. Polysaccharide containing amino sugar from Bacillus subtilis. Nature. 179:919.
21. Sharon N. 2007. Recollections. Lectins: Carbohydrate-specific reagents and biological recognition molecules. J Biol Chem. 282:275-2764.
22. Sharon N, Jeanloz RW. 1959. The isolation of an aminohexose from Bacillus subtilis. Biochim. Biochim Acta. 31:277-278.
23. Sharon N, Jeanloz RW. 1960. The diaminohexose component of a polysaccharide isolated from Bacillus subtilis. J Biol Chem. 235:1-5.
24. Sharon N, Shiff I, Zehavi U. 1964. The isolation of D-fucosamine (2-amino-2,6-dideoxy-D-galactose) from polysaccharides of Bacillus spp. Biochem J. 93:210-214.
25. Stimson E, Virji M, Makepeace K, Dell A, Morris HR, et al. 1995. Meningococcal pilin: A glycoprotein substituted with digalactosyl 2,4-diacetamio-2,4,6-trideoxyhexose. Mol Microbiol. 17:1201-1204.
26. Stoffyn PJ, Jeanloz RW.,1954. Identification of amino sugars by paper chromatography. Arch Biochem. 52:373-379.
27. Szymanski CM, Wren BW. 2005. Protein glycosylation in bacterial mucosal pathogens. Nature Revs Microbiol. 3:225-236.
28. Tsuno T, Konishi K, Naito T, Kawaguchi H. 1981. Glysperin, a new antibiotic complex of bacterial origin. II. Structure of glysperins A, B, and C. J Antibiotics (Jpn). 20:390-398.
29. Vijayakumar S, Merkx-Jacques A, Ratnayake DB, Gryski I, et al. 2006. Cj1121c, a novel UDP-4-keto-6-deoxy-GlcNAc C-4 aminotransferase essential for protein glycosylation and virulence in Campylobacter jejuni. J Biol Chem. 281:22733-22743.
30. Wacker M, Linton D, Hitchen PG, Nita-Lazar M, Haslam SM, et al. 2002. N-linked glycosylation in Campylobacter jejuni and its functional transfer into E. coli. Science. 298:1790-1793.
31. Weerapana E, Imperiali B. 2006. Asparagine-linked protein glycosylation: from eukaryotic to prokaryotic systems. Glycobiology. 16:91R-101R.
32. Young NM, Brisson JR, Kelly J, Watson DC, et al. 2002. Structure of the N-linked glycan present on multiple glycoproteins in the gram-negative bacterium, Campylobacter jejuni. J Bio Chem. 277:42530-42539.
33. Zehavi U, Sharon N. 1973. Structural studies of 4-acetamido-2-amino-2,4,6,-trideoxy-D-glucose (N acetylbacillosamine), the N-acetyl diamino sugar of Bacillus licheniformis. J Biol Chem. 248:433-438.