M6882
Methyl α-D-mannopyranoside
≥99.0% (HPLC)
Synonym(s):
α-Methyl D-mannoside
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About This Item
Empirical Formula (Hill Notation):
C7H14O6
CAS Number:
Molecular Weight:
194.18
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
210-502-3
Beilstein/REAXYS Number:
81566
MDL number:
Quality Level
assay
≥99.0% (HPLC)
form
powder or crystals
optical activity
[α]20/D 77.0 to 82.0°, c = 1-10% (w/v) in water
technique(s)
HPLC: suitable
color
white to off-white
mp
193-196 °C (lit.)
solubility
water: 100 mg/mL, clear, colorless
storage temp.
15-25°C
SMILES string
CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O
InChI
1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6+,7+/m1/s1
InChI key
HOVAGTYPODGVJG-VEIUFWFVSA-N
General description
Methyl α-D-mannopyranoside is a competitor inhibitor of the binding of mannose by Escherichia coli.
Application
Methyl α-D-mannopyranoside has been used to synthesize a series of tri- and tetrahydroxylated seven-membered iminosugars in a study that worked towards a stable noeuromycin analog with a D-manno configuration. It has also been used in a study to investigate the primary mannose binding site of pradimicin A.
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
404.1 °F
flash_point_c
206.74 °C
ppe
Eyeshields, Gloves, type N95 (US)
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M Aronson et al.
The Journal of infectious diseases, 139(3), 329-332 (1979-03-01)
Methyl alpha-D-mannopyranoside (alpha MM), a competitor inhibitor of the binding of mannose by Escherichia coli, was tested for its ability to prevent infection of the urinary tract of mice with infective strains of the organisms. Injection of the bacteria in
Yu Nakagawa et al.
Journal of the American Chemical Society, 133(43), 17485-17493 (2011-09-29)
Pradimicin A (PRM-A) is an actinomycete-derived antibiotic with the lectin-like property of being able to recognize D-mannopyranoside (Man) in the presence of Ca(2+) ion. PRM-A and its derivatives have been attracting a great deal of attention as the only family
Julia Deschamp et al.
Bioorganic & medicinal chemistry, 20(2), 641-649 (2010-10-26)
Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable D-gluco-like analogs have been reported, no data are available for D-manno-like structures. A series of tri- and tetrahydroxylated seven-membered iminosugars displaying either a D-manno-or