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. 1983 Sep;80(18):5470–5474. doi: 10.1073/pnas.80.18.5470

Asparaginylglucose: Novel type of carbohydrate linkage

Felix Wieland *, Renate Heitzer *, Wolfram Schaefer †
PMCID: PMC384279  PMID: 16593364

Abstract

The Halobacterial cell wall glycoprotein was recently shown to contain two types of sulfated saccharides: a repetitive saccharide and a nonrepetitive saccharide composed of glucuronic acid and glucose. A new type of N-glycosidic linkage is found in this latter type of saccharide: glucose is N-glycosidically linked to the polypeptide chain through the amido nitrogen of an asparagine residue, as shown by chemical analyses, proton magnetic resonance spectroscopy, and mass spectroscopy of an isolated asparaginyl saccharide. The only N-glycosidic linkage known so far is between the amido nitrogen of asparagine and N-acetylglucosamine.

Keywords: archaebacteria, cell surface glycoprotein

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Selected References

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  1. Aminoff D., Gathmann W. D., McLean C. M., Yadomae T. Quantitation of oligosaccharides released by the beta-elimination reaction. Anal Biochem. 1980 Jan 1;101(1):44–53. doi: 10.1016/0003-2697(80)90038-x. [DOI] [PubMed] [Google Scholar]
  2. Blumenkrantz N., Asboe-Hansen G. New method for quantitative determination of uronic acids. Anal Biochem. 1973 Aug;54(2):484–489. doi: 10.1016/0003-2697(73)90377-1. [DOI] [PubMed] [Google Scholar]
  3. Bonner W. M., Laskey R. A. A film detection method for tritium-labelled proteins and nucleic acids in polyacrylamide gels. Eur J Biochem. 1974 Jul 1;46(1):83–88. doi: 10.1111/j.1432-1033.1974.tb03599.x. [DOI] [PubMed] [Google Scholar]
  4. Dorland L., Schut B. L., Vliegenthart J. F., Strecker G., Fournet B., Spik G., Montreuil J. Structural studies on 2-acetamido-1-N-(4-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine and 2-acetamido-6-O-(alpha-L-fucopyranosyl)-1-N-(4-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine by 360-MHz proton-magnetic-resonance spectroscopy. Eur J Biochem. 1977 Feb 15;73(1):93–97. doi: 10.1111/j.1432-1033.1977.tb11294.x. [DOI] [PubMed] [Google Scholar]
  5. JOHANSEN P. G., MARSHALL R. D., NEUBERGER A. Carbohydrates in protein. 3 The preparation and some of the properties of a glycopeptide from hen's-egg albumin. Biochem J. 1961 Mar;78:518–527. doi: 10.1042/bj0780518. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Kirkman M. A., Burrell M. M., Lea P. J., Mills W. R. Identification and measurement of homoserine by gas--liquid chromatography. Anal Biochem. 1980 Jan 15;101(2):364–368. doi: 10.1016/0003-2697(80)90201-8. [DOI] [PubMed] [Google Scholar]
  7. König H., Kandler O. The amino acid sequence of the peptide moiety of the pseudomurein from Methanobacterium thermoautotrophicum. Arch Microbiol. 1979 Jun;121(3):271–275. doi: 10.1007/BF00425067. [DOI] [PubMed] [Google Scholar]
  8. Lehrfeld J. Differential gas-liquid chromatography method for determination of uronic acids in carbohydrate mixtures. Anal Biochem. 1981 Aug;115(2):410–418. doi: 10.1016/0003-2697(81)90026-9. [DOI] [PubMed] [Google Scholar]
  9. Mescher M. F., Strominger J. L. Purification and characterization of a prokaryotic glucoprotein from the cell envelope of Halobacterium salinarium. J Biol Chem. 1976 Apr 10;251(7):2005–2014. [PubMed] [Google Scholar]
  10. Mort A. J., Lamport D. T. Anhydrous hydrogen fluoride deglycosylates glycoproteins. Anal Biochem. 1977 Oct;82(2):289–309. doi: 10.1016/0003-2697(77)90165-8. [DOI] [PubMed] [Google Scholar]
  11. Ogata S., Lloyd K. O. Mild alkaline borohydride treatment of glycoproteins-a method for liberating both N- and O-linked carbohydrate chains. Anal Biochem. 1982 Jan 15;119(2):351–359. doi: 10.1016/0003-2697(82)90597-8. [DOI] [PubMed] [Google Scholar]
  12. Rasilo M. L., Renkonen O. Mild alkaline borohydride treatment liberates N-acetylglucosamine linked oligosaccharide chains of glycoproteins. FEBS Lett. 1981 Nov 30;135(1):38–42. doi: 10.1016/0014-5793(81)80938-6. [DOI] [PubMed] [Google Scholar]
  13. Staneloni R. J., Leloir L. F. The biosynthetic pathway of the asparagine-linked oligosaccharides of glycoproteins. CRC Crit Rev Biochem. 1982 Apr;12(4):289–326. doi: 10.1080/10409238209104422. [DOI] [PubMed] [Google Scholar]
  14. Tapuhi Y., Schmidt D. E., Lindner W., Karger B. L. Dansylation of amino acids for high-performance liquid chromatography analysis. Anal Biochem. 1981 Jul 15;115(1):123–129. doi: 10.1016/0003-2697(81)90534-0. [DOI] [PubMed] [Google Scholar]
  15. Taylor R. L., Conrad H. E. Stoichiometric depolymerization of polyuronides and glycosaminoglycuronans to monosaccharides following reduction of their carbodiimide-activated carboxyl groups. Biochemistry. 1972 Apr 11;11(8):1383–1388. doi: 10.1021/bi00758a009. [DOI] [PubMed] [Google Scholar]
  16. Wieland F., Dompert W., Bernhardt G., Sumper M. Halobacterial glycoprotein saccharides contain covalently linked sulphate. FEBS Lett. 1980 Oct 20;120(1):110–114. doi: 10.1016/0014-5793(80)81058-1. [DOI] [PubMed] [Google Scholar]
  17. Zanetta J. P., Breckenridge W. C., Vincendon G. Analysis of monosaccharides by gas-liquid chromatography of the O-methyl glycosides as trifluoroacetate derivatives. Application to glycoproteins and glycolipids. J Chromatogr. 1972 Jul 5;69(2):291–304. doi: 10.1016/s0021-9673(00)92897-8. [DOI] [PubMed] [Google Scholar]

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