Aceneuramic acid hydrate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326856

CAS#: 131-48-6

Description: Aceneuramic acid, also known as NPC-09; Ace-ER; UX-001; Neu-5Ac; SA-ER; AceER. is an immunomodulator potentially for treatment of hereditary inclusion body myopathy (HIBM). Aceneuramic acid is an N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria.


Price and Availability

Size
Price

100mg
USD 150
1g
USD 750
10g
USD 3850
Size
Price

200mg
USD 250
2g
USD 1250
20g
Ask price
Size
Price

500mg
USD 450
5g
USD 2150

N-Acetylneuraminic Acid Hydrate, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326856
Name: Aceneuramic acid hydrate
CAS#: 131-48-6
Chemical Formula: C11H21NO9
Exact Mass:
Molecular Weight: 311.287
Elemental Analysis: C, 42.44; H, 6.80; N, 4.50; O, 46.26


Synonym: NPC-09; Ace-ER; UX-001; Neu-5Ac; SA-ER; AceER; Aceneuramic acid; N-Acetylneuraminic Acid Hydrate; NANA Hydrate; Neu5Ac Hydrate.

IUPAC/Chemical Name: (2R)-2-(((2S,3S,4R,5S)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid hydrate

InChi Key: DXQYQJUKDZLOFX-JKKVJPCISA-N

InChi Code: InChI=1S/C11H19NO8.H2O/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15;/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17);1H2/t4-,6?,7+,8-,9-,11+;/m1./s1

SMILES Code: OCC1O[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H](C(O)=O)C)[C@@H]1O.[H]O[H]


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Wen L, Zheng Y, Jiang K, Zhang M, Kondengaden SM, Li S, Huang K, Li J, Song J, Wang PG. Two-Step Chemoenzymatic Detection of N-Acetylneuraminic Acid-α(2-3)-Galactose Glycans. J Am Chem Soc. 2016 Aug 30. [Epub ahead of print] PubMed PMID: 27554522.

2: Jahan M, Wynn PC, Wang B. Molecular characterization of the level of sialic acids N-acetylneuraminic acid, N-glycolylneuraminic acid, and ketodeoxynonulosonic acid in porcine milk during lactation. J Dairy Sci. 2016 Jul 13. pii: S0022-0302(16)30439-8. doi: 10.3168/jds.2016-11187. [Epub ahead of print] PubMed PMID: 27423948.

3: 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. Dataset on inflammatory proteins expressions and sialic acid levels in apolipoprotein E-deficient mice with administration of N-acetylneuraminic acid and/or quercetin. Data Brief. 2016 Jun 22;8:613-7. doi: 10.1016/j.dib.2016.06.020. eCollection 2016 Sep. PubMed PMID: 27419199; PubMed Central PMCID: PMC4936502.

4: Kim DJ, Kang MJ, Choi JA, Na DS, Kim JB, Na CS, Park JH. Anti-Helicobacter pylori activity of crude N-acetylneuraminic acid isolated from glycomacropeptide of whey. Lab Anim Res. 2016 Jun;32(2):99-104. doi: 10.5625/lar.2016.32.2.99. Epub 2016 Jun 24. PubMed PMID: 27382378; PubMed Central PMCID: PMC4931043.

5: Guo S, Tian H, Dong R, Yang N, Zhang Y, Yao S, Li Y, Zhou Y, Si Y, Qin S. Exogenous supplement of N-acetylneuraminic acid ameliorates atherosclerosis in apolipoprotein E-deficient mice. Atherosclerosis. 2016 Aug;251:183-91. doi: 10.1016/j.atherosclerosis.2016.05.032. Epub 2016 May 19. PubMed PMID: 27344369.

6: 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. Knockout of Cytidine Monophospho-N-Acetylneuraminic Acid (CMP-NeuAc) Hydroxylase From Porcine Endothelial Cells by a CRISPR System. Transplant Proc. 2016 May;48(4):1320-2. doi: 10.1016/j.transproceed.2015.10.065. PubMed PMID: 27320613.

7: Song KH, Kwak CH, Jin UH, Ha SH, Park JY, Abekura F, Chang YC, Cho SH, Lee K, Chung TW, Ha KT, Lee YC, Kim CH. Housekeeping promoter 5'pcmah-2 of pig CMP-N-acetylneuraminic acid hydroxylase gene for NeuGc expression. Glycoconj J. 2016 May 17. [Epub ahead of print] PubMed PMID: 27188588.

8: Hinneburg H, Hofmann J, Struwe WB, Thader A, Altmann F, Varón Silva D, Seeberger PH, Pagel K, Kolarich D. Distinguishing N-acetylneuraminic acid linkage isomers on glycopeptides by ion mobility-mass spectrometry. Chem Commun (Camb). 2016 Mar 21;52(23):4381-4. doi: 10.1039/c6cc01114d. PubMed PMID: 26926577.

9: Williams JT, Corcilius L, Kiefel MJ, Payne RJ. Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N-Acetylneuraminic Acid. J Org Chem. 2016 Mar 18;81(6):2607-11. doi: 10.1021/acs.joc.5b02754. Epub 2016 Mar 3. PubMed PMID: 26907566.

10: Chuanxiang W, Lian X, Lijie L, Fengli Q, Zhiwei S, Xianen Z, Jinmao Y. A sensitive and efficient method for determination of N-acetylhexosamines and N-acetylneuraminic acid in breast milk and milk-based products by high-performance liquid chromatography via UV detection and mass spectrometry identification. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Feb 1;1011:14-23. doi: 10.1016/j.jchromb.2015.12.032. Epub 2015 Dec 23. PubMed PMID: 26751589.

11: Yida Z, Imam MU, Ismail M, Ismail N, Azmi NH, Wong W, Altine Adamu H, Md Zamri ND, Ideris A, Abdullah MA. N-Acetylneuraminic Acid Supplementation Prevents High Fat Diet-Induced Insulin Resistance in Rats through Transcriptional and Nontranscriptional Mechanisms. Biomed Res Int. 2015;2015:602313. doi: 10.1155/2015/602313. Epub 2015 Nov 25. PubMed PMID: 26688813; PubMed Central PMCID: PMC4673348.

12: Yida Z, Imam MU, Ismail M, Wong W, Abdullah MA, Ideris A, Ismail N. N-Acetylneuraminic acid attenuates hypercoagulation on high fat diet-induced hyperlipidemic rats. Food Nutr Res. 2015 Dec 4;59:29046. doi: 10.3402/fnr.v59.29046. eCollection 2015. PubMed PMID: 26642300; PubMed Central PMCID: PMC4671315.

13: Yida Z, Imam MU, Ismail M, Ismail N, Ideris A, Abdullah MA. High fat diet-induced inflammation and oxidative stress are attenuated by N-acetylneuraminic acid in rats. J Biomed Sci. 2015 Oct 24;22:96. doi: 10.1186/s12929-015-0211-6. PubMed PMID: 26498218; PubMed Central PMCID: PMC4619312.

14: Takahashi T, Kawagishi S, Funahashi H, Hayashi N, Suzuki T. Production and Purification of Secretory Simian Cytidine Monophosphate-N-acetylneuraminic Acid Hydroxylase Using Baculovirus-Protein Expression System. Biol Pharm Bull. 2015;38(8):1220-6. doi: 10.1248/bpb.b15-00299. PubMed PMID: 26235586.

15: Miyagawa S, Matsunari H, Watanabe M, Nakano K, Umeyama K, Sakai R, Takayanagi S, Takeishi T, Fukuda T, Yashima S, Maeda A, Eguchi H, Okuyama H, Nagaya M, Nagashima H. Generation of α1,3-galactosyltransferase and cytidine monophospho-N-acetylneuraminic acid hydroxylase gene double-knockout pigs. J Reprod Dev. 2015;61(5):449-57. doi: 10.1262/jrd.2015-058. Epub 2015 Jul 26. PubMed PMID: 26227017; PubMed Central PMCID: PMC4623151.

16: Shi Y, Xu X, Fang M, Zhang M, Li Y, Gillespie B, Yorke S, Yang N, McKew JC, Gahl WA, Huizing M, Carrillo-Carrasco N, Wang AQ. Quantitative hydrophilic interaction chromatography-mass spectrometry analysis of N-acetylneuraminic acid and N-acetylmannosamine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Sep 1;1000:105-11. doi: 10.1016/j.jchromb.2015.07.018. Epub 2015 Jul 17. PubMed PMID: 26218770; PubMed Central PMCID: PMC4544686.

17: Pascolutti M, Madge PD, Thomson RJ, von Itzstein M. Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds. J Org Chem. 2015 Aug 7;80(15):7746-51. doi: 10.1021/acs.joc.5b00992. Epub 2015 Jul 14. PubMed PMID: 26118975.

18: Taguchi R, Minami A, Matsuda Y, Takahashi T, Otsubo T, Ikeda K, Suzuki T. Preferential Accumulation of 14C-N-Glycolylneuraminic Acid over 14C-N-Acetylneuraminic Acid in the Rat Brain after Tail Vein Injection. PLoS One. 2015 Jun 22;10(6):e0131061. doi: 10.1371/journal.pone.0131061. eCollection 2015. PubMed PMID: 26098915; PubMed Central PMCID: PMC4476740.

19: Ji W, Sun W, Feng J, Song T, Zhang D, Ouyang P, Gu Z, Xie J. Characterization of a novel N-acetylneuraminic acid lyase favoring N-acetylneuraminic acid synthesis. Sci Rep. 2015 Mar 23;5:9341. doi: 10.1038/srep09341. PubMed PMID: 25799411.

20: Colombo R, Anastasia M, Rota P, Allevi P. Correction: The first synthesis of N-acetylneuraminic acid 1,7-lactone. Chem Commun (Camb). 2015 Mar 18;51(22):4719. doi: 10.1039/c5cc90091c. PubMed PMID: 25689612.