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Methyl α-D-mannopyranoside

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

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Synonym(s):
Methyl alpha-D-mannoside, Methyl-alpha-D-mannopyranoside, α-Methyl D-mannoside
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

wgk_germany

WGK 3

flash_point_f

404.1 °F

flash_point_c

206.74 °C

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Prevention of nonspecific binding of avidin.
R C Duhamel et al.
Methods in enzymology, 184, 201-207 (1990-01-01)
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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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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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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