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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:14:27 UTC
HMDB IDHMDB0000215
Secondary Accession Numbers
  • HMDB00215
  • HMDB00533
  • HMDB14288
Metabolite Identification
Common NameN-Acetyl-D-glucosamine
DescriptionN-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703 ).
Structure
Thumb
Synonyms
ValueSource
2-acetamido-2-Deoxy-D-glucoseChEBI
GlcNAcChEBI
N-AcetylchitosamineChEBI
2-(acetylamino)-2-DeoxyhexoseHMDB
2-acetamido-2-Deoxy-D-glucopyranoseHMDB
2-acetamido-2-DeoxyglucoseHMDB
2-acetamido-D-GlucoseHMDB
2-acetylamino-2-Deoxy-D-glucoseHMDB
AcetylglucosamineHMDB
N-AcetylglucosamineHMDB
N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideHMDB
2 acetamido 2 DeoxyglucoseMeSH
N Acetyl D glucosamineMeSH
2 acetamido 2 Deoxy D glucoseMeSH
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameGlcNAc
CAS Registry Number7512-17-6
SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1
InChI KeyOVRNDRQMDRJTHS-RTRLPJTCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

    Element:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mLNot Available
LogP-2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability20.56 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-943fefe13d3449a92db7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9j-1930000000-388fd70c48f209a58653View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-1fd16b8e8608db3ef657View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-ceed8b621b338130ce76View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-8a3ade37d256b2bd4585View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3332900000-ee533266929b5b95ee4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1490000000-40dfe33adabe6ad7a7a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-2940000000-880c7b1fb58ed63f0ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-e1f07558d7921e9f24e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-8920000000-d504941e0508d1593f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9820000000-753556be259b7e745ba7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-bad102d081eb3bbc006bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
  • Lysosome
Biofluid Locations
  • Blood
  • Breast Milk
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Intestine
  • Myelin
  • Platelet
  • Prostate
Pathways
NameSMPDB/PathwhizKEGG
Amino Sugar MetabolismPw000008Pw000008 greyscalePw000008 simpleMap00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseasePw000510Pw000510 greyscalePw000510 simpleNot Available
Salla Disease/Infantile Sialic Acid Storage DiseasePw000124Pw000124 greyscalePw000124 simpleNot Available
Sialuria or French Type SialuriaPw000123Pw000123 greyscalePw000123 simpleNot Available
Sialuria or French Type SialuriaPw000222Pw000222 greyscalePw000222 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Breast MilkDetected and Quantified204.3278984 uMAdult (>18 years old)FemaleNormal details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected and Quantified2.23 +/- 1.83 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified2.40 +/- 2.35 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified21.4 +/- 18.6 uMAdult (>18 years old)Male
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Both
    Normal
      • Zerihun T. Dame, ...
    details
    SalivaDetected and Quantified3.14 +/- 2.38 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.78 +/- 3.93 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified4.41 +/- 5.98 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    UrineDetected and Quantified2.96 +/- 1.85 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedasymptomatic diverticulosis details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDDB00141
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB008032
    KNApSAcK IDNot Available
    Chemspider ID388319
    KEGG Compound IDC00140
    BioCyc IDN-acetyl-D-glucosamine
    BiGG ID34006
    Wikipedia LinkN-acetylglucosamine
    METLIN ID3356
    PubChem Compound439174
    PDB IDNGZ
    ChEBI ID506227
    References
    Synthesis ReferenceZhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
    2. Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
    3. Hatcher VB, Schwarzmann GO, Jeanloz RW, McArthur JW: Changes in the sialic acid concentration in the major cervical glycoprotein from the bonnet monkey (Macaca radiata) during a hormonally induced cycle. Fertil Steril. 1977 Jun;28(6):682-8. [PubMed:405259 ]
    4. Percheron F: [Beta-D-mannosidase]. Bull Acad Natl Med. 1995 May;179(5):881-91; discussion 892. [PubMed:7583460 ]
    5. Collard CD, Montalto MC, Reenstra WR, Buras JA, Stahl GL: Endothelial oxidative stress activates the lectin complement pathway: role of cytokeratin 1. Am J Pathol. 2001 Sep;159(3):1045-54. [PubMed:11549596 ]
    6. Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. [PubMed:1366057 ]
    7. Kottgen E, Hell B, Muller C, Kainer F, Tauber R: Developmental changes in the glycosylation and binding properties of human fibronectins. Characterization of the glycan structures and ligand binding of human fibronectins from adult plasma, cord blood and amniotic fluid. Biol Chem Hoppe Seyler. 1989 Dec;370(12):1285-94. [PubMed:2619923 ]
    8. Madrid JF, Castells MT, Martinez-Menarguez JA, Aviles M, Hernandez F, Ballesta J: Subcellular characterization of glycoproteins in the principal cells of human gallbladder. A lectin cytochemical study. Histochemistry. 1994 Mar;101(3):195-204. [PubMed:8056619 ]
    9. Weiner B, Fischer T, Waxman S: Hemostasis in the era of the chronic anticoagulated patient. J Invasive Cardiol. 2003 Nov;15(11):669-73; quiz 674. [PubMed:14608143 ]
    10. Yates AD, Watkins WM: Enzymes involved in the biosynthesis of glycoconjugates. A UDP-2-acetamido-2-deoxy-D-glucose: beta-D-galactopyranosyl-(1 leads to 4)-saccharide (1 leads to 3)-2-acetamido-2-deoxy-beta-D- glucopyranosyltransferase in human serum. Carbohydr Res. 1983 Aug 16;120:251-68. [PubMed:6226355 ]
    11. Slawson C, Housley MP, Hart GW: O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks. J Cell Biochem. 2006 Jan 1;97(1):71-83. [PubMed:16237703 ]

    Enzymes

    General function:
    Involved in ATP binding
    Specific function:
    Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
    Gene Name:
    GNE
    Uniprot ID:
    Q9Y223
    Molecular weight:
    83065.25
    General function:
    Involved in catalytic activity
    Specific function:
    Catalyzes the interconversion of N-acetylglucosamine to N-acetylmannosamine. Binds to renin forming a protein complex called high molecular weight (HMW) renin and inhibits renin activity. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
    Gene Name:
    RENBP
    Uniprot ID:
    P51606
    Molecular weight:
    48830.6
    Reactions
    N-Acetyl-D-glucosamine → N-Acetylmannosaminedetails
    References
    1. Lee YC, Wu HM, Chang YN, Wang WC, Hsu WH: The central cavity from the (alpha/alpha)6 barrel structure of Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase contains two key histidine residues for reversible conversion. J Mol Biol. 2007 Mar 30;367(3):895-908. Epub 2006 Nov 6. [PubMed:17292397 ]
    2. Lee YC, Chien HC, Hsu WH: Production of N-acetyl-D-neuraminic acid by recombinant whole cells expressing Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase and Escherichia coli N-acetyl-D-neuraminic acid lyase. J Biotechnol. 2007 May 1;129(3):453-60. Epub 2007 Feb 9. [PubMed:17349707 ]
    3. Takahashi S, Ogasawara H, Hiwatashi K, Hata K, Hori K, Koizumi Y, Sugiyama T: Amino acid residues conferring the nucleotide binding properties of N-acetyl-D-glucosamine 2-epimerase (renin binding protein). Biomed Res. 2005 Jun;26(3):117-21. [PubMed:16011304 ]
    4. Ferrero MA, Martinez-Blanco H, Lopez-Velasco FF, Ezquerro-Saenz C, Navasa N, Lozano S, Rodriguez-Aparicio LB: Purification and characterization of GlcNAc-6-P 2-epimerase from Escherichia coli K92. Acta Biochim Pol. 2007;54(2):387-99. Epub 2007 Jun 14. [PubMed:17565386 ]
    General function:
    Involved in transferase activity, transferring glycosyl groups
    Specific function:
    Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. Can produce lactose.
    Gene Name:
    B4GALT2
    Uniprot ID:
    O60909
    Molecular weight:
    41971.815
    Reactions
    Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    General function:
    Involved in transferase activity, transferring glycosyl groups
    Specific function:
    The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. The cell surface form functions as a recognition molecule during a variety of cell to cell and cell to matrix interactions, as those occurring during development and egg fertilization, by binding to specific oligosaccharide ligands on opposing cells or in the extracellular matrix.
    Gene Name:
    B4GALT1
    Uniprot ID:
    P15291
    Molecular weight:
    43919.895
    Reactions
    Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
    References
    1. Ramakrishnan B, Boeggeman E, Qasba PK: Mutation of arginine 228 to lysine enhances the glucosyltransferase activity of bovine beta-1,4-galactosyltransferase I. Biochemistry. 2005 Mar 8;44(9):3202-10. [PubMed:15736931 ]
    2. Ramasamy V, Ramakrishnan B, Boeggeman E, Ratner DM, Seeberger PH, Qasba PK: Oligosaccharide preferences of beta1,4-galactosyltransferase-I: crystal structures of Met340His mutant of human beta1,4-galactosyltransferase-I with a pentasaccharide and trisaccharides of the N-glycan moiety. J Mol Biol. 2005 Oct 14;353(1):53-67. [PubMed:16157350 ]
    3. Boeggeman E, Ramakrishnan B, Kilgore C, Khidekel N, Hsieh-Wilson LC, Simpson JT, Qasba PK: Direct identification of nonreducing GlcNAc residues on N-glycans of glycoproteins using a novel chemoenzymatic method. Bioconjug Chem. 2007 May-Jun;18(3):806-14. Epub 2007 Mar 20. [PubMed:17370997 ]
    4. Hidalgo A, Burgos V, Viola H, Medina J, Argibay P: Differential expression of glycans in the hippocampus of rats trained on an inhibitory learning paradigm. Neuropathology. 2006 Dec;26(6):501-7. [PubMed:17203585 ]
    5. Ramakrishnan B, Boeggeman E, Qasba PK: Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose. Biochemistry. 2004 Oct 5;43(39):12513-22. [PubMed:15449940 ]
    General function:
    Involved in beta-N-acetylhexosaminidase activity
    Specific function:
    Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
    Gene Name:
    HEXB
    Uniprot ID:
    P07686
    Molecular weight:
    Not Available
    General function:
    Involved in beta-N-acetylhexosaminidase activity
    Specific function:
    Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
    Gene Name:
    HEXA
    Uniprot ID:
    P06865
    Molecular weight:
    Not Available
    General function:
    Carbohydrate transport and metabolism
    Specific function:
    Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded. Also has ManNAc kinase activity.
    Gene Name:
    NAGK
    Uniprot ID:
    Q9UJ70
    Molecular weight:
    42037.295
    Reactions
    Adenosine triphosphate + N-Acetyl-D-glucosamine → ADP + N-Acetyl-D-Glucosamine 6-Phosphatedetails
    References
    1. Weihofen WA, Berger M, Chen H, Saenger W, Hinderlich S: Structures of human N-Acetylglucosamine kinase in two complexes with N-Acetylglucosamine and with ADP/glucose: insights into substrate specificity and regulation. J Mol Biol. 2006 Dec 1;364(3):388-99. Epub 2006 Sep 3. [PubMed:17010375 ]
    2. Uehara T, Park JT: The N-acetyl-D-glucosamine kinase of Escherichia coli and its role in murein recycling. J Bacteriol. 2004 Nov;186(21):7273-9. [PubMed:15489439 ]
    3. An HJ, Kim DS, Park YK, Kim SK, Choi YP, Kang S, Ding B, Cho NH: Comparative proteomics of ovarian epithelial tumors. J Proteome Res. 2006 May;5(5):1082-90. [PubMed:16674097 ]
    4. Yang C, Rodionov DA, Li X, Laikova ON, Gelfand MS, Zagnitko OP, Romine MF, Obraztsova AY, Nealson KH, Osterman AL: Comparative genomics and experimental characterization of N-acetylglucosamine utilization pathway of Shewanella oneidensis. J Biol Chem. 2006 Oct 6;281(40):29872-85. Epub 2006 Jul 20. [PubMed:16857666 ]
    5. Nishimasu H, Fushinobu S, Shoun H, Wakagi T: Crystal structures of an ATP-dependent hexokinase with broad substrate specificity from the hyperthermophilic archaeon Sulfolobus tokodaii. J Biol Chem. 2007 Mar 30;282(13):9923-31. Epub 2007 Jan 17. [PubMed:17229727 ]
    General function:
    Involved in chitin binding
    Specific function:
    Degrades chitin and chitotriose. May participate in the defense against nematodes, fungi and other pathogens. Plays a role in T-helper cell type 2 (Th2) immune response. Contributes to the response to IL-13 and inflammation in response to IL-13. Stimulates chemokine production by pulmonary epithelial cells. Protects lung epithelial cells against apoptosis and promotes phosphorylation of AKT1. Its function in the inflammatory response and in protecting cells against apoptosis is inhibited by allosamidin, suggesting that the function of this protein depends on carbohydrate binding.
    Gene Name:
    CHIA
    Uniprot ID:
    Q9BZP6
    Molecular weight:
    Not Available
    Reactions
    Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails
    General function:
    Involved in N-acetylglucosamine-1-phosphodiester alpha-
    Specific function:
    Catalyzes the second step in the formation of the mannose 6-phosphate targeting signal on lysosomal enzyme oligosaccharides by removing GlcNAc residues from GlcNAc-alpha-P-mannose moieties, which are formed in the first step.
    Gene Name:
    NAGPA
    Uniprot ID:
    Q9UK23
    Molecular weight:
    56072.49
    Reactions
    Glycoprotein N-acetyl-D-glucosaminyl-phospho-D-mannose + Water → N-Acetyl-D-glucosamine + glycoprotein phospho-D-mannosedetails
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Mullis KG, Huynh M, Kornfeld RH: Purification and kinetic parameters of bovine liver N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1994 Jan 21;269(3):1718-26. [PubMed:8294420 ]
    4. Chavez CA, Bohnsack RN, Kudo M, Gotschall RR, Canfield WM, Dahms NM: Domain 5 of the cation-independent mannose 6-phosphate receptor preferentially binds phosphodiesters (mannose 6-phosphate N-acetylglucosamine ester). Biochemistry. 2007 Nov 6;46(44):12604-17. Epub 2007 Oct 10. [PubMed:17927214 ]
    5. Kornfeld R, Bao M, Brewer K, Noll C, Canfield WM: Purification and multimeric structure of bovine N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1998 Sep 4;273(36):23203-10. [PubMed:9722550 ]
    General function:
    Involved in chitin binding
    Specific function:
    Degrades chitin, chitotriose and chitobiose. May participate in the defense against nematodes and other pathogens. Isoform 3 has no enzymatic activity.
    Gene Name:
    CHIT1
    Uniprot ID:
    Q13231
    Molecular weight:
    Not Available
    Reactions
    Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails
    General function:
    Involved in transferase activity, transferring glycosyl groups
    Specific function:
    Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
    Gene Name:
    B4GALT3
    Uniprot ID:
    O60512
    Molecular weight:
    43927.63
    Reactions
    Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    General function:
    Involved in transferase activity, transferring glycosyl groups
    Specific function:
    Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
    Gene Name:
    B4GALT4
    Uniprot ID:
    O60513
    Molecular weight:
    40040.865
    Reactions
    Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Bulter T, Schumacher T, Namdjou DJ, Gutierrez Gallego R, Clausen H, Elling L: Chemoenzymatic synthesis of biotinylated nucleotide sugars as substrates for glycosyltransferases. Chembiochem. 2001 Dec 3;2(12):884-94. [PubMed:11948877 ]
    General function:
    Involved in alpha-N-acetylglucosaminidase activity
    Specific function:
    Involved in the degradation of heparan sulfate.
    Gene Name:
    NAGLU
    Uniprot ID:
    P54802
    Molecular weight:
    Not Available
    Reactions
    + Water → + N-Acetyl-D-glucosaminedetails
    References
    1. Spiro RG: Role of N-linked polymannose oligosaccharides in targeting glycoproteins for endoplasmic reticulum-associated degradation. Cell Mol Life Sci. 2004 May;61(9):1025-41. [PubMed:15112051 ]
    2. Nogawa M, Takahashi H, Kashiwagi A, Ohshima K, Okada H, Morikawa Y: Purification and Characterization of Exo-beta-d-Glucosaminidase from a Cellulolytic Fungus, Trichoderma reesei PC-3-7. Appl Environ Microbiol. 1998 Mar;64(3):890-5. [PubMed:16349528 ]
    3. Vishu Kumar AB, Varadaraj MC, Gowda LR, Tharanathan RN: Characterization of chito-oligosaccharides prepared by chitosanolysis with the aid of papain and Pronase, and their bactericidal action against Bacillus cereus and Escherichia coli. Biochem J. 2005 Oct 15;391(Pt 2):167-75. [PubMed:15932346 ]
    4. Zou L, Yang S, Hu S, Chaudry IH, Marchase RB, Chatham JC: The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock. 2007 Apr;27(4):402-8. [PubMed:17414423 ]
    5. Shirazi F, Kulkarni M, Deshpande MV: A rapid and sensitive method for screening of chitinase inhibitors using Ostazin Brilliant Red labelled chitin as a substrate for chitinase assay. Lett Appl Microbiol. 2007 Jun;44(6):660-5. [PubMed:17576230 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in lysozyme activity
    Specific function:
    Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte- macrophage system and enhance the activity of immunoagents
    Gene Name:
    LYZ
    Uniprot ID:
    P61626
    Molecular weight:
    16536.9
    General function:
    Involved in alpha-1,3-mannosylglycoprotein 2-beta-N-acetylglucosaminyltransferase activity
    Specific function:
    Participates in O-mannosyl glycosylation. May be responsible for the synthesis of the GlcNAc(beta1-2)Man(alpha1-)O-Ser/Thr moiety on alpha-dystroglycan and other O-mannosylated proteins. Is specific for alpha linked terminal mannose and does not have MGAT3, MGAT4, MGAT5, MGAT7 or MGAT8 activity.
    Gene Name:
    POMGNT1
    Uniprot ID:
    Q8WZA1
    Molecular weight:
    75219.255
    General function:
    Involved in lysozyme activity
    Specific function:
    Hydrolysis of (1->4)-beta-linkages between N- acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins
    Gene Name:
    LYZL1
    Uniprot ID:
    Q6UWQ5
    Molecular weight:
    16654.0
    General function:
    Involved in lysozyme activity
    Specific function:
    Hydrolysis of (1->4)-beta-linkages between N- acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins
    Gene Name:
    LYZL2
    Uniprot ID:
    Q7Z4W2
    Molecular weight:
    16655.9
    General function:
    Involved in lysozyme activity
    Specific function:
    Hydrolysis of (1->4)-beta-linkages between N- acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins
    Gene Name:
    SPACA5
    Uniprot ID:
    Q96QH8
    Molecular weight:
    17896.2
    General function:
    Involved in lysozyme activity
    Specific function:
    Hydrolysis of (1->4)-beta-linkages between N- acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins
    Gene Name:
    LYZL6
    Uniprot ID:
    O75951
    Molecular weight:
    16956.2
    General function:
    Not Available
    Specific function:
    Carbohydrate-binding lectin with a preference for chitin. May play a role in defense against pathogens, or in tissue remodeling. May play an important role in the capacity of cells to respond to and cope with changes in their environment.
    Gene Name:
    CHI3L1
    Uniprot ID:
    P36222
    Molecular weight:
    Not Available
    Reactions
    Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails
    General function:
    Not Available
    Specific function:
    Lectin that binds chitooligosaccharides and other glycans with high affinity, but not heparin. Has no chitinase activity.
    Gene Name:
    CHI3L2
    Uniprot ID:
    Q15782
    Molecular weight:
    Not Available
    Reactions
    Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails
    General function:
    Not Available
    Specific function:
    Has hexosaminidase activity.
    Gene Name:
    HEXDC
    Uniprot ID:
    Q8WVB3
    Molecular weight:
    Not Available
    Reactions
    + Water → N-Acetyl-D-glucosamine + details
    General function:
    Not Available
    Specific function:
    Cleaves GlcNAc but not GalNAc from glycopeptides. Can use p-nitrophenyl-beta-GlcNAc as substrate but not p-nitrophenyl-beta-GalNAc or p-nitrophenyl-alpha-GlcNAc. Possesses hyaluronidase activity. Acetylates 'Lys-8' of histone H4 and 'Lys-14' of histone H3 (By similarity).
    Gene Name:
    MGEA5
    Uniprot ID:
    O60502
    Molecular weight:
    96930.75
    Reactions
    [Protein]-3-O-(N-acetyl-D-glucosaminyl)-L-serine + Water → [protein]-L-serine + N-Acetyl-D-glucosaminedetails
    [Protein]-3-O-(N-acetyl-D-glucosaminyl)-L-threonine + Water → [protein]-L-threonine + N-Acetyl-D-glucosaminedetails
    [Protein]-3-O-(N-acetyl-D-glucosaminyl)-L-serine + Water → [Protein]-L-serine + N-Acetyl-D-glucosaminedetails
    [Protein]-3-O-(N-acetyl-D-glucosaminyl)-L-threonine + Water → [Protein]-L-threonine + N-Acetyl-D-glucosaminedetails