Microwave-assisted synthesis of long-chain alkyl glucopyranosides

Ferlin, Nadège; Duchet, Laetitia; Kovensky, José; Grand, Éric

doi:10.1016/j.carres.2008.05.013

Cited by 19 publications

(9 citation statements)

References 25 publications

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“…Previous reports describe the synthesis of long chain alkyl glycosides with good yields by microwave-assisted solvent-free glycosylation. [12] However, in this case, no improvement was observed when this procedure was conducted with ZnCl 2 at 115 8C. Compound 8 could be isolated with slightly better yields by the Schmidt procedure, reacting trichloroacetamidate 7 [13] with 6 using BF 3 ·Et 2 O at room temperature in CH 2 Cl 2 (Scheme 1).…”

Section: Synthesismentioning

confidence: 91%

Synthetic Multimeric Heptyl Mannosides as Potent Antiadhesives of Uropathogenic Escherichia coli

et al. 2009

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Urinary tract infections caused by uropathogenic Escherichia coli presents a serious communal and nosocomial health problem initiated by bacterial adhesion to the bladder cells. E. coli expresses fimbriae with a mannose-binding adhesin, FimH, at the tip. Heptyl alpha-D-mannoside (HM) is a nanomolar inhibitor of this lectin, preventing adhesion of type 1-piliated E. coli and reducing bacteria levels in a murine cystitis model. Herein, we described the synthesis of multimeric heptyl-mannosides with valencies ranging from one to four by copper-catalyzed azide alkyne cycloaddition (CuAAC). Biological evaluation of the multivalent compounds revealed an increase in potency compared to HM. Inhibition of bladder cell binding highlighted a promising tetravalent derivative with inhibitory concentrations 6000- and 64-fold lower than mannose and HM respectively.

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Section: Synthesismentioning

confidence: 91%

Synthetic Multimeric Heptyl Mannosides as Potent Antiadhesives of Uropathogenic Escherichia coli

et al. 2009

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“…The first elements of answer are proposed by Kovensky and Ferlin in 2008. A microwave temperature of 115°C is found as a good compromise to obtain high glycosylation rates and low decomposition products contents.…”

Section: O-glycosylationsmentioning

confidence: 99%

“…Polar alcohols with low boiling/melting points lead to the formation of the corresponding thermodynamic adduct, while long chain alcohols provide preferentially the kinetic  anomer in less than 5 min. For each alcohol, an optimum reaction time, beyond which the formed alkyl glycoside is deteriorated, is estimated (Ferlin, 2008). …”

Section: O-glycosylationsmentioning

confidence: 99%

Conversion of Carbohydrates Under Microwave Heating

Richel¹,

Paquot²

2012

Carbohydrates - Comprehensive Studies on Glycobiology and Glycotechnology

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“…In addition to the introduction of the thioacyl group, isothiocyanates play a pivotal role in the preparation of a broad series of functional groups, allowing, simultaneously, the covalent coupling of a fairly unrestricted variety of structures to the saccharide moiety. For a study on their particular properties, a series of N-glucosylthiocarbamates were synthesized by Yang and co-workers [12] through the reaction of glucosyl isothiocyanate (12) with mono-and dihydric alcohols and (13)(14)(15)(16) from glucosyl isothiocyanate (12).…”

Section: Thioacylationmentioning

confidence: 99%