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Chemical Compound Review

CHITIN     N-[(2R,3R,4R,5S,6R)-2,4,5- trihydroxy-6...

Synonyms: GlcNAc, NAcGlc, betaGlcNAc, GlcNAc-beta, SureCN19345, ...
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Disease relevance of acetylglucosamine


Psychiatry related information on acetylglucosamine

  • The Id determinants were found among antibodies to NAGA and PABA made by outbred and inbred lines of White Leghorn chickens [6].

High impact information on acetylglucosamine

  • According to models of its structure, T1r3 from non-tasters is predicted to have an extra amino-terminal glycosylation site that, if used, would interfere with dimerization [7].
  • We identified five distinct beta subunit phenotypes in LAD patients: undetectable beta subunit mRNA and protein precursor; low levels of beta subunit mRNA and precursor; an aberrantly large beta subunit precursor, probably due to an extra glycosylation site; an aberrantly small precursor; and a grossly normal precursor [8].
  • At one interface, a single Ly49A subunit contacts one side of the MHC-I peptide-binding platform, presenting an open cavity towards the conserved glycosylation site on the H-2D(d) alpha2 domain [9].
  • The major gamma-gene transcribed in mature, alpha beta-bearing T cells (V gamma 1.2C gamma 2)encodes no N-linked glycosylation site so these results suggest that the fetal gamma delta receptor defines a distinct T-cell lineage whose development in the thymus precedes classical alpha beta-bearing cells [10].
  • The alpha-subunit has two and the beta-subunit one N-linked glycosylation site, and the beta-chain has in excess of four O-linked glycosylation sites [11].

Chemical compound and disease context of acetylglucosamine


Biological context of acetylglucosamine


Anatomical context of acetylglucosamine


Associations of acetylglucosamine with other chemical compounds


Gene context of acetylglucosamine

  • The vCD30 protein contains 110 aa, including a 21-residue signal peptide, a potential O-linked glycosylation site, and a 58-aa sequence sharing 51-59% identity with highly conserved extracellular segments of both mouse and human CD30 [32].
  • The Con1 glycoprotein is encoded in exon 3 of a PRB2 allele (PRB2L CON1+) with a potential N-linked glycosylation site [33].
  • We show that mutation of a single potential N-linked glycosylation site in the first immunoglobulin domain of CD22 completely abrogates ligand recognition [34].
  • A single N-linked glycosylation site is implicated in the regulation of ligand recognition by the I-type lectins CD22 and CD33 [34].
  • Using a sensitive approach that combines in-gel glycosidase and protease digestions, permethylation of released glycans, and mass spectrometry, we have elucidated for the first time the native glycoform structures of the mouse UPIa receptor and those of its non-binding homolog, UPIb, and have determined the glycosylation site occupancy [35].

Analytical, diagnostic and therapeutic context of acetylglucosamine


  1. Glycosylation of CD44 is implicated in CD44-mediated cell adhesion to hyaluronan. Bartolazzi, A., Nocks, A., Aruffo, A., Spring, F., Stamenkovic, I. J. Cell Biol. (1996) [Pubmed]
  2. Glycosylation affects cleavage of an H5N2 influenza virus hemagglutinin and regulates virulence. Deshpande, K.L., Fried, V.A., Ando, M., Webster, R.G. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  3. Hepatitis B virus (HBV) envelope glycoproteins vary drastically in their sensitivity to glycan processing: evidence that alteration of a single N-linked glycosylation site can regulate HBV secretion. Mehta, A., Lu, X., Block, T.M., Blumberg, B.S., Dwek, R.A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  4. Human c-ros-1 gene homologous to the v-ros sequence of UR2 sarcoma virus encodes for a transmembrane receptorlike molecule. Matsushime, H., Wang, L.H., Shibuya, M. Mol. Cell. Biol. (1986) [Pubmed]
  5. Class I-restricted presentation of an HIV-1 gp41 epitope containing an N-linked glycosylation site. Implications for the mechanism of processing of viral envelope proteins. Ferris, R.L., Buck, C., Hammond, S.A., Woods, A.S., Cotter, R.J., Takiguchi, M., Igarashi, Y., Ichikawa, Y., Siliciano, R.F. J. Immunol. (1996) [Pubmed]
  6. Mouse monoclonal antibodies to chicken VH idiotypic determinants reactivity with B and T cells. Chanh, T.C., Chen, C.L., Cooper, M.D. J. Immunol. (1982) [Pubmed]
  7. Tas1r3, encoding a new candidate taste receptor, is allelic to the sweet responsiveness locus Sac. Max, M., Shanker, Y.G., Huang, L., Rong, M., Liu, Z., Campagne, F., Weinstein, H., Damak, S., Margolskee, R.F. Nat. Genet. (2001) [Pubmed]
  8. Heterogeneous mutations in the beta subunit common to the LFA-1, Mac-1, and p150,95 glycoproteins cause leukocyte adhesion deficiency. Kishimoto, T.K., Hollander, N., Roberts, T.M., Anderson, D.C., Springer, T.A. Cell (1987) [Pubmed]
  9. Crystal structure of a lectin-like natural killer cell receptor bound to its MHC class I ligand. Tormo, J., Natarajan, K., Margulies, D.H., Mariuzza, R.A. Nature (1999) [Pubmed]
  10. Differential expression of two distinct T-cell receptors during thymocyte development. Pardoll, D.M., Fowlkes, B.J., Bluestone, J.A., Kruisbeek, A., Maloy, W.L., Coligan, J.E., Schwartz, R.H. Nature (1987) [Pubmed]
  11. Equine chorionic gonadotropin. Murphy, B.D., Martinuk, S.D. Endocr. Rev. (1991) [Pubmed]
  12. Molecular cloning of cDNA encoding a 55-kDa multifunctional thyroid hormone binding protein of skeletal muscle sarcoplasmic reticulum. Fliegel, L., Newton, E., Burns, K., Michalak, M. J. Biol. Chem. (1990) [Pubmed]
  13. A molecular basis for glycosylation-induced conformational switching. O'Conner, S.E., Imperiali, B. Chem. Biol. (1998) [Pubmed]
  14. Association of human immunodeficiency virus type 1 envelope glycoprotein with particles depends on interactions between the third variable and conserved regions of gp120. Willey, R.L., Martin, M.A. J. Virol. (1993) [Pubmed]
  15. Purification and specificity of bacteriolytic enzyme I from Hartmannella glebae. Upadhyay, J.M., Mares, B.A., Hemelt, D.M., Rivet, P.G. Appl. Environ. Microbiol. (1977) [Pubmed]
  16. The structure of the O-specific polysaccharide chain of Proteus penneri strain 16 lipopolysaccharide. Vinogradov, E.V., Sidorczyk, Z., Swierzko, A., Rozalski, A., Daeva, E.D., Shashkov, A.S., Knirel, Y.A., Kochetkov, N.K. Eur. J. Biochem. (1991) [Pubmed]
  17. Cr2, a candidate gene in the murine Sle1c lupus susceptibility locus, encodes a dysfunctional protein. Boackle, S.A., Holers, V.M., Chen, X., Szakonyi, G., Karp, D.R., Wakeland, E.K., Morel, L. Immunity (2001) [Pubmed]
  18. Introduction of a glycosylation site into a secreted protein provides evidence for an alternative antigen processing pathway: transport of precursors of major histocompatibility complex class I-restricted peptides from the endoplasmic reticulum to the cytosol. Bacik, I., Snyder, H.L., Antón, L.C., Russ, G., Chen, W., Bennink, J.R., Urge, L., Otvos, L., Dudkowska, B., Eisenlohr, L., Yewdell, J.W. J. Exp. Med. (1997) [Pubmed]
  19. Functions for MHC class I carbohydrates inside and outside the cell. Parham, P. Trends Biochem. Sci. (1996) [Pubmed]
  20. Cell surface expression of membrane-anchored v-sis gene products: glycosylation is not required for cell surface transport. Hannink, M., Donoghue, D.J. J. Cell Biol. (1986) [Pubmed]
  21. Dysfunctional C1 inhibitor Ta: deletion of Lys-251 results in acquisition of an N-glycosylation site. Parad, R.B., Kramer, J., Strunk, R.C., Rosen, F.S., Davis, A.E. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  22. The Bw4 public epitope of HLA-B molecules confers reactivity with natural killer cell clones that express NKB1, a putative HLA receptor. Gumperz, J.E., Litwin, V., Phillips, J.H., Lanier, L.L., Parham, P. J. Exp. Med. (1995) [Pubmed]
  23. Sequences in rotavirus glycoprotein VP7 that mediate delayed translocation and retention of the protein in the endoplasmic reticulum. Stirzaker, S.C., Poncet, D., Both, G.W. J. Cell Biol. (1990) [Pubmed]
  24. Requirement for chitin biosynthesis in epithelial tube morphogenesis. Devine, W.P., Lubarsky, B., Shaw, K., Luschnig, S., Messina, L., Krasnow, M.A. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  25. O glycosylation of an Sp1-derived peptide blocks known Sp1 protein interactions. Roos, M.D., Su, K., Baker, J.R., Kudlow, J.E. Mol. Cell. Biol. (1997) [Pubmed]
  26. Retention of fibroblast growth factor 3 in the Golgi complex may regulate its export from cells. Kiefer, P., Peters, G., Dickson, C. Mol. Cell. Biol. (1993) [Pubmed]
  27. The structure of rat preproatrial natriuretic factor as defined by a complementary DNA clone. Seidman, C.E., Duby, A.D., Choi, E., Graham, R.M., Haber, E., Homcy, C., Smith, J.A., Seidman, J.G. Science (1984) [Pubmed]
  28. Nucleotide and predicted amino acid sequences of cloned human and mouse preprocathepsin B cDNAs. Chan, S.J., San Segundo, B., McCormick, M.B., Steiner, D.F. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  29. Serotype-specific glycoprotein of simian 11 rotavirus: coding assignment and gene sequence. Both, G.W., Mattick, J.S., Bellamy, A.R. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  30. New methods for rapid separation and detection of oligosaccharides from glycoproteins. Chen, L.M., Yet, M.G., Shao, M.C. FASEB J. (1988) [Pubmed]
  31. Amyotrophic lateral sclerosis-linked glutamate transporter mutant has impaired glutamate clearance capacity. Trotti, D., Aoki, M., Pasinelli, P., Berger, U.V., Danbolt, N.C., Brown, R.H., Hediger, M.A. J. Biol. Chem. (2001) [Pubmed]
  32. Cowpox virus encodes a fifth member of the tumor necrosis factor receptor family: a soluble, secreted CD30 homologue. Panus, J.F., Smith, C.A., Ray, C.A., Smith, T.D., Patel, D.D., Pickup, D.J. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  33. PRB1, PRB2, and PRB4 coded polymorphisms among human salivary concanavalin-A binding, II-1, and Po proline-rich proteins. Azen, E.A., Amberger, E., Fisher, S., Prakobphol, A., Niece, R.L. Am. J. Hum. Genet. (1996) [Pubmed]
  34. A single N-linked glycosylation site is implicated in the regulation of ligand recognition by the I-type lectins CD22 and CD33. Sgroi, D., Nocks, A., Stamenkovic, I. J. Biol. Chem. (1996) [Pubmed]
  35. Distinct glycan structures of uroplakins Ia and Ib: structural basis for the selective binding of FimH adhesin to uroplakin Ia. Xie, B., Zhou, G., Chan, S.Y., Shapiro, E., Kong, X.P., Wu, X.R., Sun, T.T., Costello, C.E. J. Biol. Chem. (2006) [Pubmed]
  36. A signal peptide peptidase (SPP) reporter activity assay based on the cleavage of type II membrane protein substrates provides further evidence for an inverted orientation of the SPP active site relative to presenilin. Nyborg, A.C., Jansen, K., Ladd, T.B., Fauq, A., Golde, T.E. J. Biol. Chem. (2004) [Pubmed]
  37. Sequence and glycosylation site identity of two distinct glycoforms of nonspecific cross-reacting antigen as demonstrated by sequence analysis and fast atom bombardment mass spectrometry. Hefta, S.A., Paxton, R.J., Shively, J.E. J. Biol. Chem. (1990) [Pubmed]
  38. Structures of the complex glycans found on the beta-subunit of (Na,K)-ATPase. Treuheit, M.J., Costello, C.E., Kirley, T.L. J. Biol. Chem. (1993) [Pubmed]
  39. C-terminal post-translational proteolysis of plant lectins and their recombinant forms expressed in Escherichia coli. Characterization of "ragged ends" by mass spectrometry. Young, N.M., Watson, D.C., Yaguchi, M., Adar, R., Arango, R., Rodriguez-Arango, E., Sharon, N., Blay, P.K., Thibault, P. J. Biol. Chem. (1995) [Pubmed]
  40. Stable oligosaccharide microheterogeneity at individual glycosylation sites of a murine major histocompatibility antigen derived from a B-cell lymphoma. Swiedler, S.J., Hart, G.W., Tarentino, A.L., Plummer, T.H., Freed, J.H. J. Biol. Chem. (1983) [Pubmed]
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