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Merck

M6882

Méthyl α-D-mannopyranoside

≥99.0% (HPLC)

Synonyme(s) :

α-Méthyl D-mannoside

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A propos de cet article

Formule empirique (notation de Hill) :
C7H14O6
Numéro CAS:
Poids moléculaire :
194.18
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
210-502-3
Beilstein/REAXYS Number:
81566
MDL number:
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Nom du produit

Méthyl α-D-mannopyranoside, ≥99.0% (HPLC)

InChI key

HOVAGTYPODGVJG-VEIUFWFVSA-N

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

SMILES string

CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O

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

Quality Level

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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.

General description

Methyl α-D-mannopyranoside is a competitor inhibitor of the binding of mannose by Escherichia coli.

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.

Classe de stockage

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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Consulter la Bibliothèque de documents

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
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
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
Su Yu et al.
BMC gastroenterology, 9, 58-58 (2009-07-25)
GP2 is the major membrane protein present in the pancreatic zymogen granule, and is cleaved and released into the pancreatic duct along with exocrine secretions. The function of GP2 is unknown. GP2's amino acid sequence is most similar to that

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