2.0 2012-05-31 13:01:27 -0600 2015-06-03 15:53:35 -0600 ECMDB00830 M2MDB000190 N-Acetylneuraminic acid N-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-Nonulopyranosonate 5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-Nonulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonate 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonic acid 5-(acetylamino)-3,5-Dideoxy-delta-glycero-b-delta-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-delta-glycero-b-delta-galacto-2-nonulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-Nonulopyranosonate 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-Nonulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-Nonulosonate 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-Nonulosonic acid 5-(acetylamino)-3,5-Dideoxy-δ-glycero-b-δ-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-δ-glycero-b-δ-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-δ-glycero-β-δ-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-δ-glycero-β-δ-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-δ-glycero-δ-galacto-2-nonulosonate 5-(acetylamino)-3,5-Dideoxy-δ-glycero-δ-galacto-2-nonulosonic acid 5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid 5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-non-2-ulopyranosonate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonate 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonic acid 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulosonate 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulosonic acid 5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulosonate 5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulosonic acid 5-N-Acetyl-b-D-neuraminate 5-N-Acetyl-b-D-neuraminic acid 5-N-Acetyl-b-delta-neuraminate 5-N-Acetyl-b-delta-neuraminic acid 5-N-Acetyl-b-δ-neuraminate 5-N-Acetyl-b-δ-neuraminic acid 5-N-Acetyl-beta-D-neuraminate 5-N-Acetyl-beta-D-neuraminic acid 5-N-Acetyl-beta-delta-neuraminate 5-N-Acetyl-beta-delta-neuraminic acid 5-N-Acetyl-D-neuraminate 5-N-Acetyl-D-neuraminic acid 5-N-Acetyl-delta-neuraminate 5-N-Acetyl-delta-neuraminic acid 5-N-Acetyl-β-D-neuraminate 5-N-Acetyl-β-D-neuraminic acid 5-N-Acetyl-β-δ-neuraminate 5-N-Acetyl-β-δ-neuraminic acid 5-N-Acetyl-δ-neuraminate 5-N-Acetyl-δ-neuraminic acid 5-N-Acetylneuraminate 5-N-Acetylneuraminic acid N-acetylneuraminic acid Aceneuramate Aceneuramic acid Acetylneuraminate Acetylneuraminic acid B-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulopyranosonate B-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulopyranosonic acid b-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonate b-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid b-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonate b-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonic acid B-Sialate B-Sialic acid Beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulopyranosonate Beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-Nonulopyranosonic acid Beta-Sialate Beta-Sialic acid Lactaminate Lactaminic acid N-Acetyl-b-D-neuraminate N-Acetyl-b-D-neuraminic acid N-Acetyl-b-delta-neuraminate N-Acetyl-b-delta-neuraminic acid N-Acetyl-b-neuraminate N-Acetyl-b-neuraminic acid N-Acetyl-b-δ-neuraminate N-Acetyl-b-δ-neuraminic acid N-Acetyl-beta-delta-neuraminate N-Acetyl-beta-delta-neuraminic acid N-Acetyl-beta-neuraminate N-Acetyl-beta-neuraminic acid N-Acetyl-D-neuraminate N-Acetyl-D-neuraminic acid N-Acetyl-delta-neuraminate N-Acetyl-delta-neuraminic acid N-Acetyl-neuraminate N-Acetyl-neuraminic acid N-Acetyl-β-neuraminate N-Acetyl-β-neuraminic acid N-Acetyl-β-δ-neuraminate N-Acetyl-β-δ-neuraminic acid N-Acetyl-δ-neuraminate N-Acetyl-δ-neuraminic acid N-Acetylneuramate N-Acetylneuramic acid N-Acetylneuraminate N-Acetylneuraminic acid N-Acetylsialate N-Acetylsialic acid NAN NANA Neu5Ac O-Sialate O-sialic acid Sialate Sialic acid β-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonate β-5-acetamido-3,5-Dideoxy-δ-glycero-δ-galacto-nonulopyranosonic acid β-Sialate β-Sialic acid C11H19NO9 309.2699 309.105981211 (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid β-neu5ac 131-48-6 CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O 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 SQVRNKJHWKZAKO-PFQGKNLYSA-N Solid Cytosol Extra-organism Periplasm logp -2.78 ALOGPS logs -0.13 ALOGPS solubility 2.27e+02 g/l ALOGPS melting_point 186 oC logp -3.6 ChemAxon pka_strongest_acidic 3 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 309.2699 ChemAxon mono_mass 309.105981211 ChemAxon smiles CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O ChemAxon formula C11H19NO9 ChemAxon inchi 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 ChemAxon inchikey SQVRNKJHWKZAKO-PFQGKNLYSA-N ChemAxon polar_surface_area 176.78 ChemAxon refractivity 63.78 ChemAxon polarizability 27.82 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradation The 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. PW002030 Metabolic N-acetylneuraminate and N-acetylmannosamine degradation PWY0-1324 Specdb::CMs 1973 Specdb::CMs 2042 Specdb::CMs 2056 Specdb::CMs 8816 Specdb::CMs 31091 Specdb::CMs 31092 Specdb::CMs 31093 Specdb::CMs 37374 Specdb::CMs 135662 Specdb::CMs 143396 Specdb::NmrOneD 1247 Specdb::NmrOneD 143090 Specdb::NmrOneD 143091 Specdb::NmrOneD 143092 Specdb::NmrOneD 143093 Specdb::NmrOneD 143094 Specdb::NmrOneD 143095 Specdb::NmrOneD 143096 Specdb::NmrOneD 143097 Specdb::NmrOneD 143098 Specdb::NmrOneD 143099 Specdb::NmrOneD 143100 Specdb::NmrOneD 143101 Specdb::NmrOneD 143102 Specdb::NmrOneD 143103 Specdb::NmrOneD 143104 Specdb::NmrOneD 143105 Specdb::NmrOneD 143106 Specdb::NmrOneD 143107 Specdb::NmrOneD 143108 Specdb::NmrOneD 143109 Specdb::MsMs 385 Specdb::MsMs 386 Specdb::MsMs 387 Specdb::MsMs 262038 Specdb::MsMs 262039 Specdb::MsMs 262040 Specdb::MsMs 281970 Specdb::MsMs 281971 Specdb::MsMs 281972 Specdb::MsMs 2257252 Specdb::MsMs 2257346 Specdb::MsMs 2259259 Specdb::MsMs 2259295 Specdb::MsMs 2392438 Specdb::MsMs 2392439 Specdb::MsMs 2392440 Specdb::MsMs 2569712 Specdb::MsMs 2569713 Specdb::MsMs 2569714 Specdb::NmrTwoD 1002 Specdb::NmrTwoD 1225 HMDB00230 439197 392810 C19910 17012 N-ACETYLNEURAMINATE SLB N-Acetylneuraminic acid Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Tettamanti, G., Bassi, R., Viani, P., Riboni, L. (2003). "Salvage pathways in glycosphingolipid metabolism." Biochimie 85:423-437. 12770781 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. 19212411 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. 2808337 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. 6108279 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. 5082512 Rack J, Sonnenberg A: The influence of smoking and intravenous nicotine on gastric mucus. Hepatogastroenterology. 1983 Dec;30(6):258-60. 6676147 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. 2438159 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. 11175498 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. 2381164 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. 3674885 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. 11479279 Suzuki M, Suzuki A, Yamakawa T, Matsunaga E: Characterization of 2,7-anhydro-N-acetylneuraminic acid in human wet cerumen. J Biochem (Tokyo). 1985 Feb;97(2):509-15. 4008466 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. 4043964 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. 8890217 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. 7106518 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. 2070783 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. 1872812 Gopaul KP, Crook MA: Sialic acid: a novel marker of cardiovascular disease? Clin Biochem. 2006 Jul;39(7):667-81. Epub 2006 Apr 19. 16624269 Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. 11425186 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. 11287396 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. 12510390 Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM: Diversity of microbial sialic acid metabolism. Microbiol Mol Biol Rev. 2004 Mar;68(1):132-53. 15007099 Yamamoto, 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. N-acetylneuraminate lyase P0A6L4 NANA_ECOLI nanA http://ecmdb.ca/proteins/P0A6L4.xml N-acetylneuraminate epimerase P39371 NANM_ECOLI nanM http://ecmdb.ca/proteins/P39371.xml Putative sialic acid transporter B1XHJ7 NANT_ECODH nanT http://ecmdb.ca/proteins/B1XHJ7.xml Putative sialic acid transporter C4ZSW2 NANT_ECOBW nanT http://ecmdb.ca/proteins/C4ZSW2.xml Putative sialic acid transporter P41036 NANT_ECOLI nanT http://ecmdb.ca/proteins/P41036.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Probable N-acetylneuraminic acid outer membrane channel protein nanC P69856 NANC_ECOLI nanC http://ecmdb.ca/proteins/P69856.xml N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid R01811 ACNEULY-RXN N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acid R01811 N-Acetyl-alpha-neuraminate > N-Acetylneuraminic acid alpha-N-acetylneuraminate <> N-Acetylneuraminic acid R09797 N-Acetylneuraminic acid > Pyruvic acid + N-Acetylmannosamine PW_R005936