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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D-Mannose 6-phosphate sodium salt ≥98% (HPLC)

Sigma-Aldrich

M3655

D-Mannose 6-phosphate sodium salt

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
Glycan-specific metabolic oligosaccharide engineering of C7-substituted sialic acids.
Heinz Möller et al.
Angewandte Chemie (International ed. in English), 51(24), 5986-5990 (2012-06-08)
Ritu Gupta et al.
Organic letters, 11(7), 1527-1530 (2009-03-04)
In the Rh(2)(OAc)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting
Peter Chefalo et al.
Biochemistry, 45(11), 3733-3739 (2006-03-15)
Abnormal carbohydrates expressed on tumor cells, which are termed tumor-associated carbohydrate antigens (TACAs), are potential targets for the development of cancer vaccines. However, immune tolerance to TACAs has severely hindered progress in this area. To overcome this problem, we have
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