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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-11-13 07:01:10 UTC
HMDB IDHMDB0000230
Secondary Accession Numbers
  • HMDB0000800
  • HMDB00230
  • HMDB00800
Metabolite Identification
Common NameN-Acetylneuraminic acid
DescriptionN-Acetylneuraminic acid (NeuAc) (CAS: 131-48-6), also known as sialic acid, is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions that form the intermediates UDP-N-acetylglucosamine (UDP-GlcNAc), N-acetylmannosamine (ManNAc), ManNAc 6-phosphate, NeuAc 9-phosphate, and CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout human tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal glands, and the heart. Serum and urine levels of the free acid are elevated in individuals suffering from renal failure. Serum and saliva Neu5Ac levels are also elevated in alcoholics. A genetic disorder known as Salla disease or infantile NeuAc storage disease is also characterized by high serum and urine levels of this compound. The negative charge is responsible for the slippery feel of saliva and mucins coating the body's organs. This particular sialic acid is known to act as a "decoy"" for invading pathogens. Along with involvement in preventing infections (mucus associated with mucous membranes — mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection). NeuAc is also becoming known as an agent necessary for mediating ganglioside distribution and structures in the brain. Sialic acid (SA) is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. Normal human serum SA is largely bound to glycoproteins or glycolipids (total sialic acid (TSA): 1.5-2.5 mmol/L), with small amounts of free SA (1-3 umol/L). Negatively charged SA units stabilize glycoprotein conformation in cell surface receptors to increase cell rigidity. This enables signal recognition and adhesion to ligands, antibodies, enzymes, and microbes. SA residues are antigenic determinant residues in carbohydrate chains of glycolipids and glycoproteins, chemical messengers in tissue and body fluids, and may regulate glomeruli basement membrane permeability. Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity. Sialic acid is the moiety most actively recycled for metabolic purposes in the salvage pathways in glycosphingolipid metabolism. Sialic acid is indispensable for the neuritogenic activities of ganglioside constituents which are unique in that a sialic acid directly binds to the glucose of the cerebroside, they are mutually connected in tandem, and some are located in the internal parts of the sugar chain. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or another sialic acid) represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family (PMID: 11425186 , 11287396 , 12770781 , 16624269 , 12510390 , 15007099 ).
Structure
Data?1573628470
Synonyms
ValueSource
5-N-ACETYL-BETA-D-neuraminIC ACIDChEBI
beta-Neu5acChEBI
5-N-ACETYL-b-D-neuraminateGenerator
5-N-ACETYL-b-D-neuraminic acidGenerator
5-N-ACETYL-beta-D-neuraminateGenerator
5-N-ACETYL-β-D-neuraminateGenerator
5-N-ACETYL-β-D-neuraminic acidGenerator
b-Neu5acGenerator
Β-neu5acGenerator
N-AcetylneuraminateGenerator
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonateHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonateHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonateHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonateHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonic acidHMDB
5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulosonateHMDB
5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulosonic acidHMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonateHMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonic acidHMDB
5-N-Acetyl-beta-delta-neuraminic acidHMDB
5-N-Acetyl-D-neuraminateHMDB
5-N-Acetyl-D-neuraminic acidHMDB
5-N-Acetyl-delta-neuraminateHMDB
5-N-Acetyl-delta-neuraminic acidHMDB
5-N-AcetylneuraminateHMDB
5-N-Acetylneuraminic acidHMDB
AceneuramateHMDB
Aceneuramic acidHMDB
AcetylneuraminateHMDB
Acetylneuraminic acidHMDB
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonateHMDB
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonic acidHMDB
b-Sialic acidHMDB
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonateHMDB
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acidHMDB
beta-Sialic acidHMDB
LactaminateHMDB
Lactaminic acidHMDB
N-Acetyl-b-D-neuraminateHMDB
N-Acetyl-b-D-neuraminic acidHMDB
N-Acetyl-b-neuraminateHMDB
N-Acetyl-beta-delta-neuraminateHMDB
N-Acetyl-beta-delta-neuraminic acidHMDB
N-Acetyl-beta-neuraminateHMDB
N-Acetyl-D-neuraminateHMDB
N-Acetyl-D-neuraminic acidHMDB
N-Acetyl-delta-neuraminateHMDB
N-Acetyl-delta-neuraminic acidHMDB
N-Acetyl-neuraminateHMDB
N-Acetyl-neuraminic acidHMDB
N-AcetylneuramateHMDB
N-Acetylneuramic acidHMDB
N-AcetylsialateHMDB
N-Acetylsialic acidHMDB
NANHMDB
NANAHMDB
Neu5acHMDB
Sialic acidHMDB, MeSH
Acid, sialicMeSH, HMDB
Acid, N-acetylneuraminicMeSH, HMDB
N Acetylneuraminic acidMeSH, HMDB
N-Acetyl-beta-D-neuraminic acidHMDB
N-Acetyl-beta-neuraminic acidHMDB
N-Acetyl-β-D-neuraminic acidHMDB
N-Acetyl-β-neuraminic acidHMDB
N-Acetylneuraminic acidHMDB
Chemical FormulaC11H19NO9
Average Molecular Weight309.2699
Monoisotopic Molecular Weight309.105981211
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Nameβ-neu5ac
CAS Registry Number19342-33-7
SMILES
[H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
InChI KeySQVRNKJHWKZAKO-PFQGKNLYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-hydroxy acid
  • Pyran
  • Hydroxy acid
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility227 g/LALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.78 m³·mol⁻¹ChemAxon
Polarizability27.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-0fr2-1961000000-3acdbc4b39a5bf685996JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014j-0492000000-8e4279660c77b0c70a30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-00l6-1792200000-863a168c10243229e892JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fr2-1961000000-3acdbc4b39a5bf685996JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-0492000000-8e4279660c77b0c70a30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00l6-1792200000-863a168c10243229e892JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h2f-9660000000-f7a1f63f319c23f8e72aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0zfr-4620249000-1d39f85a16504ef9ea46JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0190000000-a3a5aaa2e10a6cfed08aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fk9-3900000000-7100e174e13e94736ae7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00si-9300000000-1166885a787fd53086b0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1091000000-11c42df33f8993522db0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-5090000000-5d0c74aa0d8a2c8d321cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9320000000-cfda0db8085e62f50516JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-3391000000-68ee32ef5e2ba6223c42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9110000000-9ae00577454ddf4db073JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-798cb916675bb1245a78JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
  • Nucleus
  • Lysosome
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adrenal Gland
  • Brain
  • Myelin
  • Prostate
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (1.0-3.0) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.57 +/- 1.26 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Breast MilkDetected and Quantified32.3565576 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.9 +/- 7.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified41.1 +/- 34.6 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
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 Quantified12.5 +/- 10.8 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified15.9 +/- 11.2 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified17.1 +/- 12.1 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified8.920-18.279 umol/mmol creatinineAdult (>18 years old)Not AvailableNormal details
UrineDetected and Quantified5.4 (2.5-8.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.6 +/- 1.58 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified48.621-60.502 umol/mmol creatinineAdult (>18 years old)BothSIALIDOSIS, normosomatic type details
UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
UrineDetected but not Quantified Adult (>18 years old)Both
Non–small cell lung cancer (NSCLC)
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified64.4 (31.7-225.4) umol/mmol creatinineAdult (>18 years old)BothSalla disease details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Salla disease
  1. Varho TT, Alajoki LE, Posti KM, Korhonen TT, Renlund MG, Nyman SR, Sillanpaa ML, Aula PP: Phenotypic spectrum of Salla disease, a free sialic acid storage disorder. Pediatr Neurol. 2002 Apr;26(4):267-73. [PubMed:11992753 ]
Sialidosis, normosomatic type
  1. Kobayashi T, Goto I, Tanaka Y, Yamashita M, Kuroiwa Y: Biochemical comparison of the dysmorphic type with the normosomatic type of sialidosis. Clin Chim Acta. 1980 May 9;103(3):343-7. [PubMed:7398077 ]
Associated OMIM IDs
DrugBank IDDB04265
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID392810
KEGG Compound IDC19910
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetylneuraminic acid
METLIN IDNot Available
PubChem Compound445063
PDB IDNot Available
ChEBI ID45744
Food Biomarker OntologyNot Available
VMH IDACNAM
References
Synthesis ReferenceYamamoto, Toshihiro; Teshima, Tadashi; Inami, Kaoru; Shiba, Tetsuo. Synthesis of sialic acid through aldol condensation of glucose with oxalacetic acid. Tetrahedron Letters (1992), 33(3), 325-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Domschke W, Lux G, Domschke S: Furan H2-antagonist ranitidine inhibits pentagastrin-stimulated gastric secretion stronger than cimetidine. Gastroenterology. 1980 Dec;79(6):1267-71. [PubMed:6108279 ]
  2. Bosmann HB: Platelet adhesiveness and aggregation. II. Surface sialic acid, glycoprotein: N-acetylneuraminic acid transferase, and neuraminidase of human blood platelets. Biochim Biophys Acta. 1972 Oct 25;279(3):456-74. [PubMed:5082512 ]
  3. Rack J, Sonnenberg A: The influence of smoking and intravenous nicotine on gastric mucus. Hepatogastroenterology. 1983 Dec;30(6):258-60. [PubMed:6676147 ]
  4. Bell JD, Brown JC, Nicholson JK, Sadler PJ: Assignment of resonances for 'acute-phase' glycoproteins in high resolution proton NMR spectra of human blood plasma. FEBS Lett. 1987 May 11;215(2):311-5. [PubMed:2438159 ]
  5. Brusque A, Rotta L, Pettenuzzo LF, Junqueira D, Schwarzbold CV, Wyse AT, Wannmacher CM, Dutra-Filho CS, Wajner M: Chronic postnatal administration of methylmalonic acid provokes a decrease of myelin content and ganglioside N-acetylneuraminic acid concentration in cerebrum of young rats. Braz J Med Biol Res. 2001 Feb;34(2):227-31. [PubMed:11175498 ]
  6. Seppala R, Renlund M, Bernardini I, Tietze F, Gahl WA: Renal handling of free sialic acid in normal humans and patients with Salla disease or renal disease. Lab Invest. 1990 Aug;63(2):197-203. [PubMed:2381164 ]
  7. Loomis RE, Prakobphol A, Levine MJ, Reddy MS, Jones PC: Biochemical and biophysical comparison of two mucins from human submandibular-sublingual saliva. Arch Biochem Biophys. 1987 Nov 1;258(2):452-64. [PubMed:3674885 ]
  8. Nakata D, Munster AK, Gerardy-Schahn R, Aoki N, Matsuda T, Kitajima K: Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N-acetylneuraminic acid (Neu5Ac) as substrates. Glycobiology. 2001 Aug;11(8):685-92. [PubMed:11479279 ]
  9. Suzuki M, Suzuki A, Yamakawa T, Matsunaga E: Characterization of 2,7-anhydro-N-acetylneuraminic acid in human wet cerumen. J Biochem. 1985 Feb;97(2):509-15. [PubMed:4008466 ]
  10. Baumkotter J, Cantz M, Mendla K, Baumann W, Friebolin H, Gehler J, Spranger J: N-Acetylneuraminic acid storage disease. Hum Genet. 1985;71(2):155-9. [PubMed:4043964 ]
  11. Weiss P, Tietze F, Gahl WA, Seppala R, Ashwell G: Identification of the metabolic defect in sialuria. J Biol Chem. 1989 Oct 25;264(30):17635-6. [PubMed:2808337 ]
  12. McGee DJ, Rest RF: Regulation of gonococcal sialyltransferase, lipooligosaccharide, and serum resistance by glucose, pyruvate, and lactate. Infect Immun. 1996 Nov;64(11):4630-7. [PubMed:8890217 ]
  13. Sonnenberg A, Steinkamp U, Weise A, Berges W, Wienbeck M, Rohner HG, Peter P: Salivary secretion in reflux esophagitis. Gastroenterology. 1982 Oct;83(4):889-95. [PubMed:7106518 ]
  14. Riebe D, Thorn W: Influence of carbohydrate moieties of human serum transferrin on the determination of its molecular mass by polyacrylamide gradient gel electrophoresis and staining with periodic acid-Schiff reagent. Electrophoresis. 1991 Apr;12(4):287-93. [PubMed:2070783 ]
  15. Watzlawick H, Walsh MT, Ehrhard I, Slayter HS, Haupt H, Schwick HG, Jourdian GW, Hase S, Schmid K, Brossmer R: The effect of the carbohydrate moiety upon the size and conformation of human plasma galactoglycoprotein as judged by electron microscopy and circular dichroism. Structural studies of a glycoprotein after stepwise enzymic carbohydrate removal. Biochem J. 1991 Aug 1;277 ( Pt 3):753-8. [PubMed:1872812 ]
  16. Gopaul KP, Crook MA: Sialic acid: a novel marker of cardiovascular disease? Clin Biochem. 2006 Jul;39(7):667-81. Epub 2006 Apr 19. [PubMed:16624269 ]
  17. 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 ]
  18. Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. [PubMed:11425186 ]
  19. Keppler OT, Horstkorte R, Pawlita M, Schmidt C, Reutter W: Biochemical engineering of the N-acyl side chain of sialic acid: biological implications. Glycobiology. 2001 Feb;11(2):11R-18R. [PubMed:11287396 ]
  20. Tettamanti G, Bassi R, Viani P, Riboni L: Salvage pathways in glycosphingolipid metabolism. Biochimie. 2003 Mar-Apr;85(3-4):423-37. [PubMed:12770781 ]
  21. Yamada K: [Chemo-pharmaceutical studies on the glycosphingolipid constituents from echinoderm, sea cucumbers, as the medicinal materials]. Yakugaku Zasshi. 2002 Dec;122(12):1133-43. [PubMed:12510390 ]
  22. Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM: Diversity of microbial sialic acid metabolism. Microbiol Mol Biol Rev. 2004 Mar;68(1):132-53. [PubMed:15007099 ]

Enzymes

General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular weight:
Not Available
Reactions
Galactosylceramide + N-Acetylneuraminic acid → GM4 + Waterdetails
General function:
Involved in exo-alpha-sialidase activity
Specific function:
May function in lysosomal catabolism of sialylated glycoconjugates. Has sialidase activity towards synthetic substrates, such as 2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid (4-MU-NANA or 4MU-NeuAc). Has a broad substrate specificity being active on glycoproteins, oligosaccharides and sialylated glycolipids.
Gene Name:
NEU4
Uniprot ID:
Q8WWR8
Molecular weight:
Not Available
Reactions
Galactosylceramide + N-Acetylneuraminic acid → GM4 + Waterdetails
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Catalyzes the removal of sialic acid (N-acetylneuramic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage.
Gene Name:
NEU1
Uniprot ID:
Q99519
Molecular weight:
Not Available
Reactions
Galactosylceramide + N-Acetylneuraminic acid → GM4 + Waterdetails
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:
Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:
NANS
Uniprot ID:
Q9NR45
Molecular weight:
40307.26
Reactions
Phosphoenolpyruvic acid + N-Acetylmannosamine + Water → Phosphate + N-Acetylneuraminic aciddetails
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN).
Gene Name:
CMAS
Uniprot ID:
Q8NFW8
Molecular weight:
48378.835
Reactions
Cytidine triphosphate + N-Acetylneuraminic acid → Pyrophosphate + Cytidine 5'-monophosphate-N-acetylneuraminic aciddetails
General function:
Involved in sialate O-acetylesterase activity
Specific function:
Catalyzes the removal of O-acetyl ester groups from position 9 of the parent sialic acid, N-acetylneuraminic acid.
Gene Name:
SIAE
Uniprot ID:
Q9HAT2
Molecular weight:
54572.035
Reactions
N-acetyl-O-acetylneuraminate + Water → N-Acetylneuraminic acid + Acetic aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
NANP
Uniprot ID:
Q8TBE9
Molecular weight:
27812.875
Reactions
N-Acetylneuraminic acid 9-phosphate + Water → N-Acetylneuraminic acid + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate. It prevents sialic acids from being recycled and returning to the cell surface. 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 (By similarity).
Gene Name:
NPL
Uniprot ID:
Q9BXD5
Molecular weight:
33116.95
Reactions
N-Acetylneuraminic acid → N-Acetylmannosamine + Pyruvic aciddetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
NEU1
Uniprot ID:
Q5JQI0
Molecular weight:
45467.0