N-アセチルノイラミン酸
WordNet
- the 14th letter of the Roman alphabet (同)n
PrepTutorEJDIC
- nitrogenの化学記号
- neodymiumの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/10/12 16:50:08」(JST)
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N-Acetylneuraminic acid
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Names |
IUPAC name
5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
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Identifiers |
CAS Number
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131-48-6 Y |
ChEBI |
CHEBI:61599 Y |
ChemSpider |
392681 Y |
ECHA InfoCard |
100.004.568 |
Jmol 3D model |
Interactive image |
MeSH |
N-Acetylneuraminic+Acid |
PubChem |
439197 |
InChI
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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 Y
Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N Y
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InChI=1/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
Key: SQVRNKJHWKZAKO-YRMXFSIDBI
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SMILES
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OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO
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Properties |
Chemical formula
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C11H19NO9 |
Molar mass |
309.273 g/mol |
Appearance |
White crystalline powder |
Melting point |
186 °C (367 °F; 459 K) (decomposes) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is YN ?) |
Infobox references |
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N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in mammalian cells.
This negatively charged residue is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, such as gangliosides, a crucial component of neuronal membranes found in the brain.
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).
In the biology of bacterial pathogens
Neu5Ac is also important in the biology of a member of pathogenic bacteria[1][2] as it can used either as a nutrient, providing both carbon and nitrogen to the bacterium, or in some pathogens, can be activated and placed on the cell surface.[1] Bacteria have evolved transporters for Neu5Ac to enable them to capture it from their environment and a number of these have been characterised including the NanT protein from Escherichia coli,[3] the SiaPQM TRAP transporter from Haemophilus influenzae[4] and the SatABCD ABC transporter from Haemophilus ducreyi.[5]
See also
- Neuraminic acid
- N-Glycolylneuraminic acid
- Sialic acid
References
- ^ a b Severi E, Hood DW, Thomas GH (2007). "Sialic acid utilization by bacterial pathogens". Microbiology. 153 (9): 2817–2822. doi:10.1099/mic.0.2007/009480-0. PMID 17768226.
- ^ Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM (2004). "Diversity of microbial sialic acid metabolism.". Microbiol Mol Biol Rev. 68 (1): 132–153. doi:10.1128/mmbr.68.1.132-153.2004. PMC 362108. PMID 15007099.
- ^ Vimr ER, Troy FA (1985). "Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli". J. Bacteriol. 164 (2): 845–853. PMC 214328. PMID 3902799.
- ^ Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH (2005). "Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter". Mol. Microbiol. 58 (4): 1173–1185. doi:10.1111/j.1365-2958.2005.04901.x. PMID 16262798.
- ^ Post DM, Mungur R, Gibson BW, Munson RS Jr (2005). "Identification of a novel sialic acid transporter in Haemophilus ducreyi.". Infect Immun. 73 (10): 6727–35. doi:10.1128/IAI.73.10.6727-6735.2005. PMC 1230923. PMID 16177350.
English Journal
- Inactivation of Mandelate Racemase by 3-Hydroxypyruvate Reveals a Potential Mechanistic Link between Enzyme Superfamilies.
- Nagar M1, Wyatt BN2, St Maurice M2, Bearne SL1,3.
- Biochemistry.Biochemistry.2015 May 5;54(17):2747-57. doi: 10.1021/acs.biochem.5b00221. Epub 2015 Apr 20.
- Mandelate racemase (MR), a member of the enolase superfamily, catalyzes the Mg(2+)-dependent interconversion of the enantiomers of mandelate. Several α-keto acids are modest competitive inhibitors of MR [e.g., mesoxalate (Ki = 1.8 ± 0.3 mM) and 3-fluoropyruvate (Ki = 1.3 ± 0.1 mM)], but, surprisi
- PMID 25844917
- Enhanced production of polysialic acid by metabolic engineering of Escherichia coli.
- Chen F1, Tao Y, Jin C, Xu Y, Lin BX.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2015 Mar;99(6):2603-11. doi: 10.1007/s00253-015-6391-x. Epub 2015 Jan 27.
- A number of reports have described the production of polysialic acid (PSA), focusing on the fermentation and purification of PSA. However, little work has been done to strengthen the synthetic pathway of PSA to improve PSA production. In this study, an efficient process for enhanced production of PS
- PMID 25620366
- Molecular characterization of a new N-acetylneuraminate synthase (NeuB1) from Idiomarina loihiensis.
- García García MI1, Lau K2, von Itzstein M2, García Carmona F1, Sánchez Ferrer Á3.
- Glycobiology.Glycobiology.2015 Jan;25(1):115-23. doi: 10.1093/glycob/cwu096. Epub 2014 Sep 11.
- N-Acetylneuraminate lyase synthase (NeuB; E.C. 2.5.1.56) is a key enzyme in pathogenic microorganisms for producing N-acetylneuraminic acid through the irreversible condensation of N-acetylmannosamine (ManNAc) and phosphoenolpyruvate (PEP). However, nothing is known about this enzyme in non-pathogen
- PMID 25214154
Japanese Journal
- N-アセチルノイラミン酸およびN-アセチル-D-マンノサミンの簡易大量製造法
- Trends in glycoscience and glycotechnology 18(102), 245-252, 2006-06-30
- NAID 10019281905
- Why Is Sialic Acid Attracting Interest Now? Complete Enzymatic Synthesis of Sialic Acid with N-Acylglucosamine 2-Epimerase
- Journal of bioscience and bioengineering 93(3), 258-265, 2002-03-25
- NAID 110002684730
- A Facile Synthesis of 2-Deoxy-2,3-didehydroneuraminic Acid Derivatives
Related Links
- Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on 'small' chemical compounds. ... ChEBI Name N-acetylneuraminate ChEBI ID
- Summary: Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. N-acetylneuraminate, the most ...
Related Pictures
★リンクテーブル★
[★]
- 英
- N-acetylneuraminate, N-acetylneuraminic acid, NANA
- 関
- シアル酸、酸性糖タンパク
[★]
- 関
- number of experiment、sample size
- pの前の[n]はmと記載する。synptom→symptom
[★]
[★]
ネオジム neodymium