M4670
D-Mannosamine hydrochloride
≥98% (HPLC)
Synonym(s):
2-Amino-2-deoxy-D-mannose hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C6H13NO5 · HCl
CAS Number:
Molecular Weight:
215.63
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
226-847-8
Beilstein/REAXYS Number:
3914860
MDL number:
Quality Level
biological source
crab (shell), shrimp shells
assay
≥98% (HPLC)
form
powder
technique(s)
HPLC: suitable
color
white
mp
168 °C (dec.) (lit.)
solubility
water: 50 mg/mL, clear, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
Cl[H].N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI
1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3+,4-,5-,6?;/m1./s1
InChI key
QKPLRMLTKYXDST-OHXGPSCHSA-N
Application
D-Mannosamine hydrochloride can be used for the synthesis of non-natural ManNAc analogs for the expression of thiols on cell-surface sialic acids. It has been used in a study to investigate the synthesis and high-throughput screening of N-acetyl-β-hexosaminidase inhibitor libraries targeting osteoarthritis.
Other Notes
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Junjie Liu et al.
The Journal of organic chemistry, 69(19), 6273-6283 (2004-09-11)
C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-beta-hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose.
Srinivasa-Gopalan Sampathkumar et al.
Nature protocols, 1(5), 2377-2385 (2007-04-05)
The sialic acid biosynthetic pathway in mammalian cells utilizes N-acetyl-D-mannosamine (ManNAc) as a natural metabolic precursor and has the remarkable ability to biosynthetically process non-natural ManNAc analogs. Herein, we describe a recipe-style protocol for the synthesis of the novel peracetylated
Monica De Caroli et al.
The Plant journal : for cell and molecular biology, 65(2), 295-308 (2011-01-13)
The secretory pathway in plants involves sustained traffic to the cell wall, as matrix components, polysaccharides and proteins reach the cell wall through the endomembrane system. We studied the secretion pattern of cell-wall proteins in tobacco protoplasts and leaf epidermal
Filippo Bonaccorsi et al.
Carbohydrate research, 344(12), 1442-1448 (2009-05-27)
The recently described [Attolino, E.; Bonaccorsi, F.; Catelani, G.; D'Andrea, F. Carbohydr. Res. 2008, 343, 2545-2556.] beta-D-MaNAcp-(1-->4)-beta-D-Glcp thiophenyl glycosyl donor 3 was used in alpha-glycosylation reactions of OH-2 and OH-3 of the suitably protected p-MeO-benzyl alpha-l-rhamnopyranoside acceptors 7 and 8.
Alyaa Ibrahim et al.
Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques, 13(2), 128-135 (2010-09-08)
An improved HPLC method with fluorescence detection was developed and validated for determination of glucosamine in human and rat biological samples. Aliquot of 0.1 mL plasma was spiked with mannosamine HCl as the internal standard (IS); proteins were precipitated with
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