N-acetylneuraminate

N-アセチルノイラミン酸

WordNet

1. the 14th letter of the Roman alphabet (同)n

PrepTutorEJDIC

1. nitrogenの化学記号
2. 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

Names
IUPAC name 5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Identifiers
CAS Number	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 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 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
SMILES OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO
Properties
Chemical formula	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).
Y verify (what is YN ?)
Infobox references

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 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. 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, the SiaPQM TRAP transporter from Haemophilus influenzae and the SatABCD ABC transporter from Haemophilus ducreyi.

See also

• Neuraminic acid
• N-Glycolylneuraminic acid
• Sialic acid

References

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

• Chemical & pharmaceutical bulletin 48(1), 163-165, 2000-01-01
• NAID 110003635296

Related Links

• N-acetylneuraminate (CHEBI:35418) - EMBL European ...

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

• MetaCyc N-acetylneuraminate

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

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★リンクテーブル★

リンク元	「N-アセチルノイラミン酸」
関連記事	「n」「N」「Nd」

「N-アセチルノイラミン酸」

　　[★]

英

N-acetylneuraminate, N-acetylneuraminic acid, NANA

関

シアル酸、酸性糖タンパク

「n」

　　[★]

• n.

• 例数

関

number of experiment、sample size

• pの前の[n]はmと記載する。synptom→symptom

「N」

　　[★]

• アスパラギン asparagine
• 窒素(原子、分子)

　 　

「Nd」

　　[★] ネオジム neodymium