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Merck

67770

Methyl α-D-mannopyranoside

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

Sinónimos:

Methyl alpha-D-mannoside, Methyl-alpha-D-mannopyranoside, α-Methyl D-mannoside

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Fórmula empírica (notación de Hill):
C7H14O6
Número CAS:
617-04-9
Peso molecular:
194.18
UNSPSC Code:
41106212
NACRES:
NA.85
PubChem Substance ID:
329760486
EC Number:
210-502-3
Beilstein/REAXYS Number:
81566
MDL number:
MFCD00063262

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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% (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

Quality Level

200

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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

Clase de almacenamiento

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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Certificados de análisis (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)
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
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
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
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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