ECMDB: N-Acetylneuraminic acid (ECMDB00830) (M2MDB000190)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)Transporters (6)XML

Proteins (8)

Record Information

Version

2.0

Creation Date

2012-05-31 13:01:27 -0600

Update Date

2015-06-03 15:53:35 -0600

Secondary Accession Numbers

ECMDB00830

Identification

Name:

N-Acetylneuraminic acid

Description

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)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

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

Chemical Formula:

C₁₁H₁₉NO₉

Weight:

Average: 309.2699
Monoisotopic: 309.105981211

InChI Key:

SQVRNKJHWKZAKO-PFQGKNLYSA-N

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

CAS number:

131-48-6

IUPAC Name:

(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional IUPAC Name:

β-neu5ac

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetylneuraminic acid (CHEBI:45744 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

186 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	227 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.6	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	176.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.78 m³·mol⁻¹	ChemAxon
Polarizability	27.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid
N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acid
N-Acetyl-alpha-neuraminate > N-Acetylneuraminic acid
alpha-N-acetylneuraminate <> N-Acetylneuraminic acid
N-Acetylneuraminic acid > Pyruvic acid + N-Acetylmannosamine

SMPDB Pathways:

N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradation

PW002030

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520

EcoCyc Pathways:

N-acetylneuraminate and N-acetylmannosamine degradation PWY0-1324

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (7 TMS)	splash10-0fr2-1961000000-3acdbc4b39a5bf685996	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-014j-0492000000-8e4279660c77b0c70a30	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-00l6-1792200000-863a168c10243229e892	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fr2-1961000000-3acdbc4b39a5bf685996	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014j-0492000000-8e4279660c77b0c70a30	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00l6-1792200000-863a168c10243229e892	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h2f-9660000000-f7a1f63f319c23f8e72a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0zfr-4620249000-1d39f85a16504ef9ea46	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0190000000-a3a5aaa2e10a6cfed08a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0fk9-3900000000-7100e174e13e94736ae7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00si-9300000000-1166885a787fd53086b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1091000000-11c42df33f8993522db0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-5090000000-5d0c74aa0d8a2c8d321c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9320000000-cfda0db8085e62f50516	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-3391000000-68ee32ef5e2ba6223c42	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9110000000-9ae00577454ddf4db073	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-798cb916675bb1245a78	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
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
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
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
Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. Pubmed: 11425186
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
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
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. Pubmed: 22080510
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
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. Pubmed: 21097882
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
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
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
Rack J, Sonnenberg A: The influence of smoking and intravenous nicotine on gastric mucus. Hepatogastroenterology. 1983 Dec;30(6):258-60. Pubmed: 6676147
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
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
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
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. Pubmed: 19212411
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. Pubmed: 4008466
Tettamanti, G., Bassi, R., Viani, P., Riboni, L. (2003). "Salvage pathways in glycosphingolipid metabolism." Biochimie 85:423-437. Pubmed: 12770781
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. Pubmed: 17765195
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
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
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
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. Pubmed: 18331064
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

Synthesis Reference:

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.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17012
HMDB ID	HMDB00230
Pubchem Compound ID	439197
Kegg ID	C19910
ChemSpider ID	392810
Wikipedia	N-Acetylneuraminic acid
BioCyc ID	N-ACETYLNEURAMINATE
EcoCyc ID	N-ACETYLNEURAMINATE
Ligand Expo	SLB

Enzymes

Protein Details

1. N-acetylneuraminate lyase

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
Gene Name:: nanA
Uniprot ID:: P0A6L4
Molecular weight:: 32593

Reactions

N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate.

Protein Details

2. N-acetylneuraminate epimerase

General function:: Involved in racemase and epimerase activity, acting on
Specific function:: Converts alpha-N-acetylneuranimic acid (Neu5Ac) to the beta-anomer, accelerating the equilibrium between the alpha- and beta-anomers. Probably facilitates sialidase-negative bacteria to compete sucessfully for limited amounts of extracellular Neu5Ac, which is likely taken up in the beta-anomer. In addition, the rapid removal of sialic acid from solution might be advantageous to the bacterium to damp down host responses
Gene Name:: nanM
Uniprot ID:: P39371
Molecular weight:: 39572

Reactions

N-acetyl-alpha-neuraminate = N-acetyl-beta-neuraminate.

Transporters

Protein Details

1. Putative sialic acid transporter

General function:: Involved in transmembrane transport
Specific function:: May be a sugar-cation symporter involved in sialic acid uptake
Gene Name:: nanT
Uniprot ID:: B1XHJ7
Molecular weight:: 53551

Protein Details

2. Putative sialic acid transporter

General function:: Involved in transmembrane transport
Specific function:: May be a sugar-cation symporter involved in sialic acid uptake
Gene Name:: nanT
Uniprot ID:: C4ZSW2
Molecular weight:: 53551

Protein Details

3. Putative sialic acid transporter

General function:: Involved in transmembrane transport
Specific function:: May be a sugar-cation symporter involved in sialic acid transport as it is required for sialic acid uptake
Gene Name:: nanT
Uniprot ID:: P41036
Molecular weight:: 53551

Protein Details

4. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

5. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Protein Details

6. Probable N-acetylneuraminic acid outer membrane channel protein nanC

General function:: Involved in oligosaccharide transporting porin activity
Specific function:: Outer membrane channel protein allowing the entry of N- acetylneuraminic acid (Neu5Ac or sialic acid) into the bacteria (Probable). NanC proteins form high-conductance channels which are open at low membrane potentials and which have a weak anion selectivity
Gene Name:: nanC
Uniprot ID:: P69856
Molecular weight:: 27888

N-Acetylneuraminic acid (ECMDB00830) (M2MDB000190)

Structure for #<Compound:0xaeb9d83c>

Enzymes

Reactions

Reactions

Transporters