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Methyl α-D-mannopyranoside

≥99.0%, suitable for microbiology, enables differentiation between species of Listeria

Synonym(s):

Methyl alpha-D-mannoside, Methyl-alpha-D-mannopyranoside, 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/REAXYS Number:
81566
EC Number:
210-502-3
MDL number:
MFCD00063262
UNSPSC Code:
41106212
PubChem Substance ID:
329760486
NACRES:
NA.85

Quality Level

200

assay

≥99.0% (sum of enantiomers, HPLC)
≥99.0%

form

powder

optical activity

[α]20/D 77.0 to 82.0°, c = 10% in H2O

mol wt

194.18 g/mol

mp

187-195 °C
193-196 °C (lit.)

solubility

H2O: 0.1 g/mL, clear, colorless

application(s)

microbiology

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 compound that belongs to the class of organic compounds known as o-glycosyl compounds. It is used for the differentiation of Listeria species, Listeria monocytogenes, Listeria innocua, and Listeria welshimeri can ferment the sugar, producing acid which can be identified using an appropriate pH indicator. It has been used to synthesize a series of tri- and tetrahydroxylated seven-membered imino sugars in a study that worked towards a stable Noeuromycin (glycosyl cation mimic that strongly inhibits glycosidases) analog with a D-manno configuration. It has also been used in a study to investigate the primary mannose-binding site of Pradimicin A. (antifungal agent)

Application

Methyl α-D-mannopyranoside can be used to identify different species of Listeria based on their ability to ferment the sugar.

Other Notes

Unwanted binding of avidin to endogenous lectins

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

404.1 °F

flash_point_c

206.74 °C

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH9843
BCCH9700
BCCH3991
BCCH6884
BCCG2787

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Prevention of nonspecific binding of avidin.
R C Duhamel et al.
Methods in enzymology, 184, 201-207 (1990-01-01)
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
Rafael Maldonado-Hernández et al.
Analytical biochemistry, 610, 113887-113887 (2020-08-09)
Over the past 10 years we have been developing a multi-attribute analytical platform that allows for the preparation of milligram amounts of functional, high-pure, and stable Torpedo (muscle-type) nAChR detergent complexes for crystallization purpose. In the present work, we have
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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Base Ingredients of Microbiology Media

Culture media provides a habitat with suitable nutrients, energy sources, and certain environmental conditions for the growth of microorganisms. The components of the culture media range from simple sugars to peptones, salts, antibiotics, and complex indicators.

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