N-Acetylneuraminic acid

• CAT Number: I001209
• CAS Number: 131-48-6
• Molecular Formula: C11H19NO9
• Molecular Weight: 309.3
• Purity: ≥95%
• Target: immunomodulator
• Solubility: H2O: 50 mg/mL
• Storage: -20°C
• IUPAC Name: (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 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
• InChIKey: SQVRNKJHWKZAKO-PFQGKNLYSA-N
• SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O

N-Acetylneuraminic acid (Cat No.: I001209) is a carbohydrate that widely exists in nature, and is also the basic component of many glycoproteins, glycopeptides and glycolipids. It has a wide range of biological functions, such as the regulation of blood protein half-life, multiple Neutralization of a toxin, cell adhesion, immune antigen-antibody response, and protection against cell lysis. The biochemical derivatives of N-Acetylneuraminic acid are also commonly used in the synthesis of drugs.

Reference

1:Corrigendum: Characterization of a novel N-acetylneuraminic acid lyase favoring industrial N-acetylneuraminic acid synthesis process. Ji W, Sun W, Feng J, Song T, Zhang D, Ouyang P, Gu Z, Xie J.Sci Rep. 2017 Apr 28;7:42268. doi: 10.1038/srep42268. No abstract available. PMID: 28452364 Free PMC Article2:Structure elucidation and analysis of biosynthesis genes of the O-antigen of Escherichia coli O131 containing N-acetylneuraminic acid. Perepelov AV, Guo X, Senchenkova SN, Shashkov AS, Liu B, Knirel YA.Carbohydr Res. 2016 Dec 21;436:41-44. doi: 10.1016/j.carres.2016.11.003. Epub 2016 Nov 4. PMID: 27863302 3:Molecular Characterization of the Cytidine Monophosphate-N-Acetylneuraminic Acid Hydroxylase (CMAH) Gene Associated with the Feline AB Blood Group System. Omi T, Nakazawa S, Udagawa C, Tada N, Ochiai K, Chong YH, Kato Y, Mitsui H, Gin A, Oda H, Azakami D, Tamura K, Sako T, Inagaki T, Sakamoto A, Tsutsui T, Bonkobara M, Tsuchida S, Ikemoto S.PLoS One. 2016 Oct 18;11(10):e0165000. doi: 10.1371/journal.pone.0165000. eCollection 2016. PMID: 27755584 Free PMC Article4:Production of α1,3-galactosyltransferase and cytidine monophosphate-N-acetylneuraminic acid hydroxylase gene double-deficient pigs by CRISPR/Cas9 and handmade cloning. Gao H, Zhao C, Xiang X, Li Y, Zhao Y, Li Z, Pan D, Dai Y, Hara H, Cooper DK, Cai Z, Mou L.J Reprod Dev. 2017 Feb 16;63(1):17-26. doi: 10.1262/jrd.2016-079. Epub 2016 Oct 8. PMID: 27725344 Free PMC Article5:Two-Step Chemoenzymatic Detection of N-Acetylneuraminic Acid-α(2-3)-Galactose Glycans. Wen L, Zheng Y, Jiang K, Zhang M, Kondengaden SM, Li S, Huang K, Li J, Song J, Wang PG.J Am Chem Soc. 2016 Sep 14;138(36):11473-6. doi: 10.1021/jacs.6b07132. Epub 2016 Aug 30. PMID: 27554522 6:Molecular characterization of the level of sialic acids N-acetylneuraminic acid, N-glycolylneuraminic acid, and ketodeoxynonulosonic acid in porcine milk during lactation. Jahan M, Wynn PC, Wang B.J Dairy Sci. 2016 Oct;99(10):8431-42. doi: 10.3168/jds.2016-11187. Epub 2016 Aug 8. PMID: 27423948 7:Dataset on inflammatory proteins expressions and sialic acid levels in apolipoprotein E-deficient mice with administration of N-acetylneuraminic acid and/or quercetin. Dong R, Li F, Qin S, Wang Y, Si Y, Xu X, Tian H, Zhai L, Zhang G, Li Y, Zhou Y, Zhang Y, Zhang N, Guo S.Data Brief. 2016 Jun 22;8:613-7. doi: 10.1016/j.dib.2016.06.020. eCollection 2016 Sep. PMID: 27419199 Free PMC Article8:Anti-Helicobacter pylori activity of crude N-acetylneuraminic acid isolated from glycomacropeptide of whey. Kim DJ, Kang MJ, Choi JA, Na DS, Kim JB, Na CS, Park JH.Lab Anim Res. 2016 Jun;32(2):99-104. doi: 10.5625/lar.2016.32.2.99. Epub 2016 Jun 24. PMID: 27382378 Free PMC Article9:Exogenous supplement of N-acetylneuraminic acid ameliorates atherosclerosis in apolipoprotein E-deficient mice. Guo S, Tian H, Dong R, Yang N, Zhang Y, Yao S, Li Y, Zhou Y, Si Y, Qin S.Atherosclerosis. 2016 Aug;251:183-91. doi: 10.1016/j.atherosclerosis.2016.05.032. Epub 2016 May 19. PMID: 27344369 10:Knockout of Cytidine Monophospho-N-Acetylneuraminic Acid (CMP-NeuAc) Hydroxylase From Porcine Endothelial Cells by a CRISPR System. Sakai R, Esaki Y, Hasuwa H, Ikawa M, Lo P, Matsuura R, Nakahata K, Zenitani M, Asada M, Maeda A, Eguchi H, Okuyama H, Miyagawa S.Transplant Proc. 2016 May;48(4):1320-2. doi: 10.1016/j.transproceed.2015.10.065. PMID: 27320613