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M4670

Sigma-Aldrich

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:
5505-63-5
Molecular Weight:
215.63
Beilstein:
3914860
EC Number:
226-847-8
MDL number:
MFCD00064557
UNSPSC Code:
12352201
PubChem Substance ID:
24896935
NACRES:
NA.25

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

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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.
Tal Gefen et al.
Vaccine, 28(51), 8197-8202 (2010-09-30)
Passive immunization with cross-species antibodies triggers the patient's immune response, thereby preventing repeated treatment. Mannosamine-biotin adduct (MBA) has been described as a masking agent for immunogenic reduction and here, the immunogenicity and biological activity of MBA-coated horse anti-viper venom (hsIgG)
Christopher Brigham et al.
Journal of bacteriology, 191(11), 3629-3638 (2009-03-24)
We characterized the nanLET operon in Bacteroides fragilis, whose products are required for the utilization of the sialic acid N-acetyl neuraminic acid (NANA) as a carbon and energy source. The first gene of the operon is nanL, which codes for
Anabel Elisa Rodríguez et al.
Veterinary parasitology, 167(2-4), 227-235 (2009-10-17)
Autonomous glycosylphosphatidylinositol (GPI) molecules (also protein-free GPIs or free GPIs) have been reported to be particularly abundant in some parasitic protozoa and mediate strong immunomodulatory effects on the host immune system. In the work at hand we have investigated the
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