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
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]
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 239.224 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
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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.
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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.
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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.
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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.
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