Record Information
Version2.0
Creation Date2012-08-15 08:51:31 -0600
Update Date2015-09-13 15:15:33 -0600
Secondary Accession Numbers
  • ECMDB21648
Identification
Name:Chitin
DescriptionChitin (C8H13O5N)n is a long-chain polymer of a N-acetylglucosamine, a derivative of glucose, and is found in many places throughout the natural world. It is the main component of the cell walls of fungi, the exoskeletons of arthropods such as crustaceans (e.g., crabs, lobsters and shrimps) and insects, the radulas of mollusks, and the beaks of cephalopods, including squid and octopuses. In terms of structure, chitin may be compared to the polysaccharide cellulose and, in terms of function, to the protein keratin. It is a polysaccharide; it is constructed from units of acetylglucosamine (more completely, N-acetyl-D-glucos-2-amine). These are linked together in beta-1,4 fashion (in a similar manner to the glucose units which form cellulose). In effect chitin may be described as cellulose with one hydroxyl group on each monomer replaced by an acetylamine group. This allows for increased hydrogen bonding between adjacent polymers, giving the polymer increased strength. A linear polysaccharide of beta-1->4 linked units of acetylglucosamine. It is the second most abundant biopolymer on earth, found especially in insects and fungi. When deacetylated it is called chitosan. Chitosan is prepared from chitin by deacetylation.
Structure
Thumb
Synonyms:
  • (1RIght4)-2-acetamido-2-deoxy-b-D-glucan
  • (1right4)-2-acetamido-2-deoxy-beta-D-glucan
  • (1RIght4)-2-acetamido-2-deoxy-β-D-glucan
  • b-1,4-Poly-N-acetyl-D-glucosamine
  • b-1,4-Poly-N-acetyl-delta-glucosamine
  • b-1,4-Poly-N-acetyl-δ-glucosamine
  • Beta-1,4-Poly-N-acetyl-D-glucosamine
  • Beta-1,4-Poly-N-acetyl-delta-glucosamine
  • Chitin
  • Poly 2-Acetamido-2-deoxy-D-glucose
  • Poly 2-Acetamido-2-deoxy-delta-glucose
  • Poly 2-acetamido-2-deoxy-δ-glucose
  • [1,4-(N-Acetyl-b-D-glucosaminyl)]N
  • [1,4-(N-Acetyl-b-D-glucosaminyl)]n+1
  • [1,4-(N-Acetyl-b-delta-glucosaminyl)]N
  • [1,4-(N-Acetyl-b-delta-glucosaminyl)]n+1
  • [1,4-(N-Acetyl-b-δ-glucosaminyl)]N
  • [1,4-(N-Acetyl-b-δ-glucosaminyl)]n+1
  • [1,4-(N-Acetyl-beta-D-glucosaminyl)]N
  • [1,4-(N-Acetyl-beta-D-glucosaminyl)]N+1
  • [1,4-(N-Acetyl-beta-delta-glucosaminyl)]N
  • [1,4-(N-Acetyl-beta-delta-glucosaminyl)]N+1
  • [1,4-(N-Acetyl-β-D-glucosaminyl)]N
  • [1,4-(N-Acetyl-β-D-glucosaminyl)]n+1
  • [1,4-(N-Acetyl-β-δ-glucosaminyl)]N
  • [1,4-(N-Acetyl-β-δ-glucosaminyl)]n+1
  • [4Close-b-D-glcpnacopen1Right]N
  • [4close-beta-D-GlcpNAcopen1right]N
  • [4Close-β-D-glcpnacopen1Right]N
  • β-1,4-Poly-N-acetyl-D-glucosamine
  • β-1,4-Poly-N-acetyl-δ-glucosamine
Chemical Formula:C28H49N3O16
Weight:Average: 683.6992
Monoisotopic: 683.311282535
InChI Key:DJHJJVWPFGHIPH-OODMECLYSA-N
InChI:InChI=1S/C28H49N3O16/c1-11(35)29-21-19(9-44-8-15-17(5-33)47-28(42)23(25(15)39)31-13(3)37)45-16(4-32)14(24(21)38)7-43-10-20-22(30-12(2)36)27(41)26(40)18(6-34)46-20/h14-28,32-34,38-42H,4-10H2,1-3H3,(H,29,35)(H,30,36)(H,31,37)/t14-,15-,16?,17?,18?,19+,20+,21?,22?,23?,24+,25+,26-,27-,28-/m1/s1
CAS number:1398-61-4
IUPAC Name:Not Available
Traditional IUPAC Name:Not Available
SMILES:CC(=O)NC1[C@H](O)OC(CO)[C@@H](COC[C@@H]2OC(CO)[C@@H](COC[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3NC(C)=O)[C@H](O)C2NC(C)=O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:Not Available
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility75.8 g/LALOGPS
logP-2.5ALOGPS
logS-0.92ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0020195000-2e6a56a958abe902a3e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-11ec-0273492000-ace7f79ec49825bd5fd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmr-6594462000-c3586d5d836795b9e53aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006w-1352911000-863eeeb6aa19c4b1a13eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2344295000-9c0b132184373172725cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-4957010000-d6d15cd685b32cc6a8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ai-0000190000-6edcc24d4bf1dd7ae865View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5001391000-7e5b14aac0963d66ab7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9022240000-288bdbd056f808dedbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-116r-0251519000-1653bc016143a1446468View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m99-3941354000-8656850f46179cee5b75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qi-7900000000-d7d93fd040c9f9381f77View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Farnia P, Mohammadi F, Zarifi Z, Tabatabee DJ, Ganavi J, Ghazisaeedi K, Farnia PK, Gheydi M, Bahadori M, Masjedi MR, Velayati AA: Improving sensitivity of direct microscopy for detection of acid-fast bacilli in sputum: use of chitin in mucus digestion. J Clin Microbiol. 2002 Feb;40(2):508-11. Pubmed: 11825964
  • Gheri G, Sgambati E, Thyrion GD, Vichi D, Orlandini GE: The oligosaccharidic content of the glycoconjugates of the prepubertal descended and undescended testis: lectin histochemical study. Ital J Anat Embryol. 2004 Apr-Jun;109(2):69-84. Pubmed: 15481156
  • 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
  • Howling GI, Dettmar PW, Goddard PA, Hampson FC, Dornish M, Wood EJ: The effect of chitin and chitosan on the proliferation of human skin fibroblasts and keratinocytes in vitro. Biomaterials. 2001 Nov;22(22):2959-66. Pubmed: 11575470
  • Ishihara C, Yoshimatsu K, Tsuji M, Arikawa J, Saiki I, Tokura S, Azuma I: Anti-viral activity of sulfated chitin derivatives against Friend murine leukaemia and herpes simplex type-1 viruses. Vaccine. 1993;11(6):670-4. Pubmed: 8391740
  • Johnson SM, Pappagianis D: The coccidioidal complement fixation and immunodiffusion-complement fixation antigen is a chitinase. Infect Immun. 1992 Jul;60(7):2588-92. Pubmed: 1612728
  • Kawashita M, Nakao M, Minoda M, Kim HM, Beppu T, Miyamoto T, Kokubo T, Nakamura T: Apatite-forming ability of carboxyl group-containing polymer gels in a simulated body fluid. Biomaterials. 2003 Jun;24(14):2477-84. Pubmed: 12695074
  • Nakajima M, Atsumi K, Kifune K, Miura K, Kanamaru H: Chitin is an effective material for sutures. Jpn J Surg. 1986 Nov;16(6):418-24. Pubmed: 3820865
  • Piskun RP, Pentiuk AA, Serkova VK, Polesia TL, Savitskaia EA: [Enterosorbents in the treatment of atherosclerosis] Eksp Klin Farmakol. 1998 Mar-Apr;61(2):69-74. Pubmed: 9621181
  • Sano H, Matsukubo T, Shibasaki K, Itoi H, Takaesu Y: Inhibition of adsorption of oral streptococci to saliva treated hydroxyapatite by chitin derivatives. Bull Tokyo Dent Coll. 1991 Feb;32(1):9-17. Pubmed: 1668072
  • Sharaev PN, Strelkov NS, Sannikova AA, Zvorykin IA, Men'shikova NN, Sakhabutdinova EP, Gabdrakhmanova NK: [The method for detection of urinary lysozyme] Klin Lab Diagn. 2001 Apr;(4):52-3. Pubmed: 11393034
  • Shibuya N, Nakamura K, Ogoshi K, Ohta T, Hori Y, Kodama K, Yamamoto M: Modification of mutagenic activities of pro-mutagens by glyco-ursodeoxycholic acid in the Ames assay. Tohoku J Exp Med. 1999 Sep;189(1):1-9. Pubmed: 10622203
  • Soule JB, Halverson AL, Becker RB, Pistole MC, Orenstein JM: A patient with acquired immunodeficiency syndrome and untreated Encephalitozoon (Septata) intestinalis microsporidiosis leading to small bowel perforation. Response to albendazole. Arch Pathol Lab Med. 1997 Aug;121(8):880-7. Pubmed: 9278619
  • Vasstrand EN, Jensen HB: Affinity chromatography of human saliva lysozyme and effect of pH and ionic strength on lytic activity. Scand J Dent Res. 1980 Jun;88(3):219-28. Pubmed: 6932088
  • Xu Y, Olman V, Xu D: Clustering gene expression data using a graph-theoretic approach: an application of minimum spanning trees. Bioinformatics. 2002 Apr;18(4):536-45. Pubmed: 12016051
  • Zampini M, Pruzzo C, Bondre VP, Tarsi R, Cosmo M, Bacciaglia A, Chhabra A, Srivastava R, Srivastava BS: Vibrio cholerae persistence in aquatic environments and colonization of intestinal cells: involvement of a common adhesion mechanism. FEMS Microbiol Lett. 2005 Mar 15;244(2):267-73. Pubmed: 15766778
Synthesis Reference:Kurita, Keisuke; Koyama, Yoshiyuki; Nishimura, Shinichiro; Kamiya, Mami. Facile preparation of water-soluble chitin from chitosan. Chemistry Letters (1989), (9), 1597-8.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17029
HMDB IDHMDB03362
Pubchem Compound ID453624
Kegg IDC00461
ChemSpider ID399508
WikipediaChitin
BioCyc IDNot Available

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Bifunctional enzyme with lysozyme/chitinase activity
Gene Name:
chiA
Uniprot ID:
P13656
Molecular weight:
97057
Reactions
Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins.
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.

Transporters

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Bifunctional enzyme with lysozyme/chitinase activity
Gene Name:
chiA
Uniprot ID:
P13656
Molecular weight:
97057
Reactions
Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins.
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.