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M6882

Sigma-Aldrich

Methyl α-D-mannopyranoside

≥99.0% (HPLC)

Synonym(s):

α-Methyl D-mannoside

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MXP 1,385.00
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25 G
MXP 1,385.00
100 G
MXP 3,730.00
500 G
MXP 17,039.00

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

MXP 1,385.00

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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. [1]

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. [2] It has also been used in a study to investigate the primary mannose binding site of pradimicin A. [3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK7248
BCBS9531
BCCH8893
BCCJ5032
BCCF9932

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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
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
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
View All Related Papers

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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