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M6882

Sigma-Aldrich

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:
617-04-9
Molecular Weight:
194.18
Beilstein:
81566
EC Number:
210-502-3
MDL number:
MFCD00063262
UNSPSC Code:
12352201
PubChem Substance ID:
24897124
NACRES:
NA.25

Quality Level

300

Assay

≥99.0% (HPLC)

form

powder

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

404.1 °F

Flash Point(C)

206.74 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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