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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
Christian M Cole et al.
Chembiochem : a European journal of chemical biology, 14(2), 205-208 (2013-01-08)
Sugar coated: We recently developed methylcyclopropenes as low-molecular-weight tetrazine coupling partners. Here, we demonstrate that methylcyclopropenes can meet the stringent steric demands required for metabolic imaging of unnatural mannosamines on live cells. Using sequential azide-alkyne chemistry, we also demonstrate multicolor
Yasuhiko Iwasaki et al.
Chemical communications (Cambridge, England), 47(37), 10329-10331 (2011-08-20)
In order to obtain cell microarrays formed with human promyelocytic leukemia cells (HL-60), biotinylation of methacryloyl-functionalized HL-60 cells was performed via a thiol-ene reaction with thiol-terminated 4-arm poly(ethylene glycol) (PEG(4)10K-SH). Biotinylated HL-60 cells were selectively adhered onto an avidin-patterned surface
Hesham H Salman et al.
Vaccine, 27(35), 4784-4790 (2009-06-23)
Bioadhesive poly(anhydride) nanoparticles coated with mannose (M-NP) or Salmonella Enteritidis derived flagellin (F-NP) were designed to be applied in oral vaccination strategies using ovalbumin (OVA) as antigen model. Nanoparticles formulations (OVA-M-NP, OVA-F-NP and control OVA-NP) were characterized and evaluated in
Feng Liu et al.
Biochemistry, 48(39), 9194-9201 (2009-09-02)
The Neisseria meningitidis sialic acid synthase (NeuB) catalyzes the metal-dependent condensation of N-acetylmannosamine (ManNAc) and phosphoenolpyruvate (PEP) to generate N-acetylneuraminic acid (NeuAc or sialic acid). N. meningitidis is a causative agent of meningitis and produces a capsular polysaccharide comprised of
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