2.02012-05-31 13:01:27 -06002015-06-03 15:53:35 -0600ECMDB00830M2MDB000190N-Acetylneuraminic acidN-acetylneuraminic acid (NeuAc) or sialic acid (SA) 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: UDP-N-acetylglucosamine (UDP-GlcNAc) -> N-acetylmannosamine (ManNAc) -> ManNAc 6-phosphate -> NeuAc 9-phosphate -> NeuAc -> CMP-NeuAc. SA is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. 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. SA are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host SA is to regulate innate immunity. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or linked to 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: 12770781, 15007099)5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-Nonulopyranosonate5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-Nonulopyranosonic acid5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonate5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonic acid5-(acetylamino)-3,5-Dideoxy-delta-glycero-b-delta-galacto-2-nonulopyranosonate5-(acetylamino)-3,5-Dideoxy-delta-glycero-b-delta-galacto-2-nonulopyranosonic acid5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-Nonulopyranosonate5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-Nonulopyranosonic acid5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-Nonulosonate5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-Nonulosonic acid5-(acetylamino)-3,5-Dideoxy-δ-glycero-b-δ-galacto-2-nonulopyranosonate5-(acetylamino)-3,5-Dideoxy-δ-glycero-b-δ-galacto-2-nonulopyranosonic acid5-(acetylamino)-3,5-Dideoxy-δ-glycero-β-δ-galacto-2-nonulopyranosonate5-(acetylamino)-3,5-Dideoxy-δ-glycero-β-δ-galacto-2-nonulopyranosonic acid5-(acetylamino)-3,5-Dideoxy-δ-glycero-δ-galacto-2-nonulosonate5-(acetylamino)-3,5-Dideoxy-δ-glycero-δ-galacto-2-nonulosonic acid5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonate5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-non-2-ulopyranosonate5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonate5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonic acid5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulosonate5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulosonic acid5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulosonate5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulosonic acid5-N-Acetyl-b-D-neuraminate5-N-Acetyl-b-D-neuraminic acid5-N-Acetyl-b-delta-neuraminate5-N-Acetyl-b-delta-neuraminic acid5-N-Acetyl-b-δ-neuraminate5-N-Acetyl-b-δ-neuraminic acid5-N-Acetyl-beta-D-neuraminate5-N-Acetyl-beta-D-neuraminic acid5-N-Acetyl-beta-delta-neuraminate5-N-Acetyl-beta-delta-neuraminic acid5-N-Acetyl-D-neuraminate5-N-Acetyl-D-neuraminic acid5-N-Acetyl-delta-neuraminate5-N-Acetyl-delta-neuraminic acid5-N-Acetyl-β-D-neuraminate5-N-Acetyl-β-D-neuraminic acid5-N-Acetyl-β-δ-neuraminate5-N-Acetyl-β-δ-neuraminic acid5-N-Acetyl-δ-neuraminate5-N-Acetyl-δ-neuraminic acid5-N-Acetylneuraminate5-N-Acetylneuraminic acid<i>N</i>-acetylneuraminic acidAceneuramateAceneuramic acidAcetylneuraminateAcetylneuraminic acidB-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-NonulopyranosonateB-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulopyranosonic acidb-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonateb-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acidb-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonateb-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonic acidB-SialateB-Sialic acidBeta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-NonulopyranosonateBeta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulopyranosonic acidBeta-SialateBeta-Sialic acidLactaminateLactaminic acidN-Acetyl-b-D-neuraminateN-Acetyl-b-D-neuraminic acidN-Acetyl-b-delta-neuraminateN-Acetyl-b-delta-neuraminic acidN-Acetyl-b-neuraminateN-Acetyl-b-neuraminic acidN-Acetyl-b-δ-neuraminateN-Acetyl-b-δ-neuraminic acidN-Acetyl-beta-delta-neuraminateN-Acetyl-beta-delta-neuraminic acidN-Acetyl-beta-neuraminateN-Acetyl-beta-neuraminic acidN-Acetyl-D-neuraminateN-Acetyl-D-neuraminic acidN-Acetyl-delta-neuraminateN-Acetyl-delta-neuraminic acidN-Acetyl-neuraminateN-Acetyl-neuraminic acidN-Acetyl-β-neuraminateN-Acetyl-β-neuraminic acidN-Acetyl-β-δ-neuraminateN-Acetyl-β-δ-neuraminic acidN-Acetyl-δ-neuraminateN-Acetyl-δ-neuraminic acidN-AcetylneuramateN-Acetylneuramic acidN-AcetylneuraminateN-Acetylneuraminic acidN-AcetylsialateN-Acetylsialic acidNANNANANeu5AcO-SialateO-sialic acidSialateSialic acidβ-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonateβ-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonic acidβ-Sialateβ-Sialic acidC11H19NO9309.2699309.105981211(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidβ-neu5ac131-48-6CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=OInChI=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/s1SQVRNKJHWKZAKO-PFQGKNLYSA-NSolidCytosolExtra-organismPeriplasmlogp-2.78logs-0.13solubility2.27e+02 g/lmelting_point186 oClogp-3.6pka_strongest_acidic3pka_strongest_basic-1.3iupac(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidaverage_mass309.2699mono_mass309.105981211smilesCC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=OformulaC11H19NO9inchiInChI=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/s1inchikeySQVRNKJHWKZAKO-PFQGKNLYSA-Npolar_surface_area176.78refractivity63.78polarizability27.82rotatable_bond_count5acceptor_count9donor_count7physiological_charge-1formal_charge0Amino sugar and nucleotide sugar metabolismec00520N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradationThe degradation of N-acetylneuraminate begins with its incorporation into the cytosol through a hydrogen symporter. Once inside the cytosol it is degraded by a N-acetylneuraminate lyase resulting in a release of a pyruvic acid and N-acetymannosamine. The latter compound is phosphorylated by an ATP driven N-Acetylmannosamine kinase resulting in the release of an ADP, a hydrogen ion and a N-Acetyl-D-mannosamine 6-phosphate. This phosphorylated compound is then metabolized by a putative N-acetylmannosamine-6-phosphate 2-epimerase resulting in the release of a N-Acetyl-D-glucosamine 6-phosphate. This compound is then deacetylated through a N-acetylglucosamine-6-phosphate deacetylase resulting in the release of an Acetic acid and a glucosamine 6-phosphate This compound can then be deaminated through a glucosamine-6-phosphate deaminase resulting in the release of an ammonium and a beta-D-fructofuranose 6-phosphate which can then be incorporated into the glycolysis pathway.
PW002030Metabolic<i>N</i>-acetylneuraminate and <i>N</i>-acetylmannosamine degradationPWY0-1324Specdb::CMs1973Specdb::CMs2042Specdb::CMs2056Specdb::CMs8816Specdb::CMs31091Specdb::CMs31092Specdb::CMs31093Specdb::CMs37374Specdb::CMs135662Specdb::CMs143396Specdb::NmrOneD1247Specdb::NmrOneD143090Specdb::NmrOneD143091Specdb::NmrOneD143092Specdb::NmrOneD143093Specdb::NmrOneD143094Specdb::NmrOneD143095Specdb::NmrOneD143096Specdb::NmrOneD143097Specdb::NmrOneD143098Specdb::NmrOneD143099Specdb::NmrOneD143100Specdb::NmrOneD143101Specdb::NmrOneD143102Specdb::NmrOneD143103Specdb::NmrOneD143104Specdb::NmrOneD143105Specdb::NmrOneD143106Specdb::NmrOneD143107Specdb::NmrOneD143108Specdb::NmrOneD143109Specdb::MsMs385Specdb::MsMs386Specdb::MsMs387Specdb::MsMs262038Specdb::MsMs262039Specdb::MsMs262040Specdb::MsMs281970Specdb::MsMs281971Specdb::MsMs281972Specdb::MsMs2257252Specdb::MsMs2257346Specdb::MsMs2259259Specdb::MsMs2259295Specdb::MsMs2392438Specdb::MsMs2392439Specdb::MsMs2392440Specdb::MsMs2569712Specdb::MsMs2569713Specdb::MsMs2569714Specdb::NmrTwoD1002Specdb::NmrTwoD1225HMDB00230439197392810C1991017012N-ACETYLNEURAMINATESLBN-Acetylneuraminic acidKeseler, I. 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Tetrahedron Letters (1992), 33(3), 325-8.N-acetylneuraminate lyaseP0A6L4NANA_ECOLInanAhttp://ecmdb.ca/proteins/P0A6L4.xmlN-acetylneuraminate epimeraseP39371NANM_ECOLInanMhttp://ecmdb.ca/proteins/P39371.xmlPutative sialic acid transporterB1XHJ7NANT_ECODHnanThttp://ecmdb.ca/proteins/B1XHJ7.xmlPutative sialic acid transporterC4ZSW2NANT_ECOBWnanThttp://ecmdb.ca/proteins/C4ZSW2.xmlPutative sialic acid transporterP41036NANT_ECOLInanThttp://ecmdb.ca/proteins/P41036.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlProbable N-acetylneuraminic acid outer membrane channel protein nanCP69856NANC_ECOLInanChttp://ecmdb.ca/proteins/P69856.xmlN-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acidR01811ACNEULY-RXNN-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acidR01811N-Acetyl-alpha-neuraminate > N-Acetylneuraminic acidalpha-N-acetylneuraminate <> N-Acetylneuraminic acidR09797 N-Acetylneuraminic acid > Pyruvic acid + N-AcetylmannosaminePW_R005936