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M6882

Sigma-Aldrich

Méthyl α-D-mannopyranoside

≥99.0% (HPLC)

Synonyme(s) :

α-Méthyl D-mannoside

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About This Item

Formule empirique (notation de Hill):
C7H14O6
Numéro CAS:
617-04-9
Poids moléculaire :
194.18
Numéro Beilstein :
81566
Numéro CE :
210-502-3
Numéro MDL:
MFCD00063262
Code UNSPSC :
12352201
ID de substance PubChem :
24897124
Nomenclature NACRES :
NA.25

Pureté

≥99.0% (HPLC)

Forme

powder

Activité optique

[α]20/D 77.0 to 82.0°, c = 1-10% (w/v) in water

Technique(s)

HPLC: suitable

Couleur

white to off-white

Pf

193-196 °C (lit.)

Solubilité

water: 100 mg/mL, clear, colorless

Température de stockage

15-25°C

Chaîne SMILES 

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

Clé InChI

HOVAGTYPODGVJG-VEIUFWFVSA-N

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Description générale

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.

Autres remarques

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

404.1 °F

Point d'éclair (°C)

206.74 °C

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
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
Karen T Welch et al.
Bioorganic & medicinal chemistry letters, 18(24), 6573-6575 (2008-11-08)
A virtual screening approach was used to identify new glycomimetics. The National Cancer Institute Diversity Set was docked into the carbohydrate binding site of the lectin concanavalin A (ConA). The resulting poses were analyzed and 19 molecules were tested for
Oliver Schwardt et al.
Bioorganic & medicinal chemistry, 19(21), 6454-6473 (2011-10-04)
Urinary tract infection (UTI) caused by uropathogenic Escherichia coli (UPEC) is one of the most prevalent infectious diseases. Particularly affected are women, who have a 40-50% risk to experience at least one symptomatic UTI episode at some time during their
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