N-Acetylmannosamine hydrate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529808

CAS#: 3615-17-6

Description: N-Acetylmannosamine, also known as ManNAc, DEX M-74, N-acetyl-D-mannosamine, is a drug potentially for the treatment of hereditary inclusion body myopathy


Price and Availability

Size
Price

1g
USD 250
Size
Price

2g
USD 450
Size
Price

5g
USD 850

N-Acetylmannosamine hydrate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529808
Name: N-Acetylmannosamine hydrate
CAS#: 3615-17-6
Chemical Formula: C8H17NO7
Exact Mass: 221.09
Molecular Weight: 239.224
Elemental Analysis: C, 40.17; H, 7.16; N, 5.86; O, 46.82


Related CAS #: 3615-17-6   4773-29-9    

Synonym: DEX-M-74; DEX M-74; DEXM74; DEX M 74; ManNAc; N-Acetylmannosamine

IUPAC/Chemical Name: N-((2S,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)acetamide hydrate

InChi Key: KVWIBLJBIFTKIZ-XNJRRJNCSA-N

InChi Code: InChI=1S/C8H15NO6.H2O/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11;/h2,5-8,11,13-15H,3H2,1H3,(H,9,12);1H2/t5-,6-,7-,8-;/m1./s1

SMILES Code: CC(N[C@@H]([C@@H](O)[C@H](O)[C@H](O)CO)C=O)=O.[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: 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. PubMed PMID: 26218770; PubMed Central PMCID: PMC4544686.

2: Kuwahara M, Ito K, Hayakawa K, Yagi S, Shiota K. N-Acetylmannosamine improves sleep-wake quality in middle-aged mice: relevance to autonomic nervous function. Auton Neurosci. 2015 Jan;187:56-62. doi: 10.1016/j.autneu.2014.11.005. PubMed PMID: 25443216.

3: Wratil PR, Rigol S, Solecka B, Kohla G, Kannicht C, Reutter W, Giannis A, Nguyen LD. A novel approach to decrease sialic acid expression in cells by a C-3-modified N-acetylmannosamine. J Biol Chem. 2014 Nov 14;289(46):32056-63. doi: 10.1074/jbc.M114.608398. PubMed PMID: 25278018; PubMed Central PMCID: PMC4231682.

4: Liu N, Wang ZK, Wang HX, Li Y, Niu ZH, Yu XF. Muscle biopsy and UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase gene mutation analysis in two Chinese patients with distal myopathy with rimmed vacuoles. Neuroreport. 2015 Jul 8;26(10):598-601. doi: 10.1097/WNR.0000000000000396. PubMed PMID: 26053703.

5: North RA, Kessans SA, Griffin MD, Watson AJ, Fairbanks AJ, Dobson RC. Cloning, expression, purification, crystallization and preliminary X-ray diffraction analysis of N-acetylmannosamine-6-phosphate 2-epimerase from methicillin-resistant Staphylococcus aureus. Acta Crystallogr F Struct Biol Commun. 2014 May;70(Pt 5):650-5. doi: 10.1107/S2053230X14007171. PubMed PMID: 24817730; PubMed Central PMCID: PMC4014339.

6: North RA, Seizova S, Stampfli A, Kessans SA, Suzuki H, Griffin MD, Kvansakul M, Dobson RC. Cloning, expression, purification, crystallization and preliminary X-ray diffraction analysis of N-acetylmannosamine kinase from methicillin-resistant Staphylococcus aureus. Acta Crystallogr F Struct Biol Commun. 2014 May;70(Pt 5):643-9. doi: 10.1107/S2053230X14007250. PubMed PMID: 24817729; PubMed Central PMCID: PMC4014338.

7: Pélissier MC, Sebban-Kreuzer C, Guerlesquin F, Brannigan JA, Bourne Y, Vincent F. Structural and functional characterization of the Clostridium perfringens N-acetylmannosamine-6-phosphate 2-epimerase essential for the sialic acid salvage pathway. J Biol Chem. 2014 Dec 19;289(51):35215-24. doi: 10.1074/jbc.M114.604272. PubMed PMID: 25320079; PubMed Central PMCID: PMC4271210.

8: Martinez J, Nguyen LD, Hinderlich S, Zimmer R, Tauberger E, Reutter W, Saenger W, Fan H, Moniot S. Crystal structures of N-acetylmannosamine kinase provide insights into enzyme activity and inhibition. J Biol Chem. 2012 Apr 20;287(17):13656-65. doi: 10.1074/jbc.M111.318170. PubMed PMID: 22343627; PubMed Central PMCID: PMC3340156.

9: Kikusui T, Shimozawa A, Kitagawa A, Nagasawa M, Mogi K, Yagi S, Shiota K. N-acetylmannosamine improves object recognition and hippocampal cell proliferation in middle-aged mice. Biosci Biotechnol Biochem. 2012;76(12):2249-54. PubMed PMID: 23221698.

10: Malicdan MC, Noguchi S, Tokutomi T, Goto Y, Nonaka I, Hayashi YK, Nishino I. Peracetylated N-acetylmannosamine, a synthetic sugar molecule, efficiently rescues muscle phenotype and biochemical defects in mouse model of sialic acid-deficient myopathy. J Biol Chem. 2012 Jan 20;287(4):2689-705. doi: 10.1074/jbc.M111.297051. PubMed PMID: 22157763; PubMed Central PMCID: PMC3268427.

11: Bond MR, Zhang H, Kim J, Yu SH, Yang F, Patrie SM, Kohler JJ. Metabolism of diazirine-modified N-acetylmannosamine analogues to photo-cross-linking sialosides. Bioconjug Chem. 2011 Sep 21;22(9):1811-23. doi: 10.1021/bc2002117. PubMed PMID: 21838313; PubMed Central PMCID: PMC3178686.

12: Mori-Yoshimura M, Monma K, Suzuki N, Aoki M, Kumamoto T, Tanaka K, Tomimitsu H, Nakano S, Sonoo M, Shimizu J, Sugie K, Nakamura H, Oya Y, Hayashi YK, Malicdan MC, Noguchi S, Murata M, Nishino I. Heterozygous UDP-GlcNAc 2-epimerase and N-acetylmannosamine kinase domain mutations in the GNE gene result in a less severe GNE myopathy phenotype compared to homozygous N-acetylmannosamine kinase domain mutations. J Neurol Sci. 2012 Jul 15;318(1-2):100-5. doi: 10.1016/j.jns.2012.03.016. PubMed PMID: 22507750.

13: Zhang L, Muthana MM, Yu H, McArthur JB, Qu J, Chen X. Characterizing non-hydrolyzing Neisseria meningitidis serogroup A UDP-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase using UDP-N-acetylmannosamine (UDP-ManNAc) and derivatives. Carbohydr Res. 2016 Jan;419:18-28. doi: 10.1016/j.carres.2015.10.016. PubMed PMID: 26598987; PubMed Central PMCID: PMC4698195.

14: Harazi A, Becker-Cohen M, Zer H, Moshel O, Hinderlich S, Mitrani-Rosenbaum S. The Interaction of UDP-N-Acetylglucosamine 2-Epimerase/N-Acetylmannosamine Kinase (GNE) and Alpha-Actinin 2 Is Altered in GNE Myopathy M743T Mutant. Mol Neurobiol. 2016 Mar 29. [Epub ahead of print] PubMed PMID: 27023225.

15: Kim BS, Hwang J, Kim MH, Choi SH. Cooperative regulation of the Vibrio vulnificus nan gene cluster by NanR protein, cAMP receptor protein, and N-acetylmannosamine 6-phosphate. J Biol Chem. 2011 Nov 25;286(47):40889-99. doi: 10.1074/jbc.M111.300988. PubMed PMID: 21956110; PubMed Central PMCID: PMC3220468.

16: Möller H, Böhrsch V, Lucka L, Hackenberger CP, Hinderlich S. Efficient metabolic oligosaccharide engineering of glycoproteins by UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) knock-down. Mol Biosyst. 2011 Jul;7(7):2245-51. doi: 10.1039/c1mb05059a. PubMed PMID: 21584309.

17: Kemmner W, Kessel P, Sanchez-Ruderisch H, Möller H, Hinderlich S, Schlag PM, Detjen K. Loss of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) induces apoptotic processes in pancreatic carcinoma cells. FASEB J. 2012 Feb;26(2):938-46. doi: 10.1096/fj.11-186700. PubMed PMID: 22049060.

18: D'Elia MA, Henderson JA, Beveridge TJ, Heinrichs DE, Brown ED. The N-acetylmannosamine transferase catalyzes the first committed step of teichoic acid assembly in Bacillus subtilis and Staphylococcus aureus. J Bacteriol. 2009 Jun;191(12):4030-4. doi: 10.1128/JB.00611-08. PubMed PMID: 19376878; PubMed Central PMCID: PMC2698391.

19: Reinke SO, Eidenschink C, Jay CM, Hinderlich S. Biochemical characterization of human and murine isoforms of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE). Glycoconj J. 2009 May;26(4):415-22. doi: 10.1007/s10719-008-9189-6. PubMed PMID: 18815882.

20: Galeano B, Klootwijk R, Manoli I, Sun M, Ciccone C, Darvish D, Starost MF, Zerfas PM, Hoffmann VJ, Hoogstraten-Miller S, Krasnewich DM, Gahl WA, Huizing M. Mutation in the key enzyme of sialic acid biosynthesis causes severe glomerular proteinuria and is rescued by N-acetylmannosamine. J Clin Invest. 2007 Jun;117(6):1585-94. PubMed PMID: 17549255; PubMed Central PMCID: PMC1878529.