Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water

Liautard, Virginie; Desvergnes, Valérie; Martin, Olivier R.

doi:10.1016/j.tetasy.2008.08.006

Cited by 22 publications

(5 citation statements)

References 44 publications

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“…It is interesting to note that compound 31 , with the same absolute stereochemistry as Gal f , showed no activity. Liautard et al synthesized two Gal f disaccharide mimics containing iminogalactitol moieties ( 32 , 33 )92 by the same 1,3‐dipolar cycloaddition methodology as described earlier 67. These compounds were designed as potential galactofuranosyltransferase inhibitors; however, no biological data have been reported.…”

Section: Biosynthesis Of Galf Residuesmentioning

confidence: 99%

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

2009

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The thermodynamically less stable form of galactose-galactofuranose (Galf)-is essential for the viability of several pathogenic species of bacteria and protozoa but absent in this form in mammals, so the biochemical pathways by which Galf-containing glycans are assembled and catabolysed are attractive sites for drug action. This potential has led to increasing interest in the synthesis of molecules containing Galf residues, their subsequent use in studies directed towards understanding the enzymes that process these residues and the identification of potential inhibitors of these pathways. Major achievements of the past several years have included an in-depth understanding of the mechanism of UDP-galactopyranose mutase (UGM), the enzyme that produces UDP-Galf, which is the donor species for galactofuranosyltransferases. A number of methods for the synthesis of galactofuranosides have also been developed, and practitioners in the field now have many options for the initiation of a synthesis of glycoconjugates containing either alpha- or beta-Galf residues. UDP-Galf has also been prepared by a number of approaches, and it appears that a chemoenzymatic approach is currently the most viable method for producing multi-milligram amounts of this important intermediate. Recent advances both in the understanding of the mechanism of UGM and in the synthesis of galactofuranose and its derivatives are highlighted in this review.

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Section: Biosynthesis Of Galf Residuesmentioning

confidence: 99%

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

2009

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“…In the course of our work on the synthesis and uses of carbohydrate-derived nitrones, it appeared that these intermediates could give access not only to a variety of iminosugars but also to their N -hydroxy derivatives, as soon as a method was available for deprotecting alkoxy groups without affecting NO bonds . Strikingly, while a few polyhydroxylated piperidine N -oxides have been previously studied, the potential of polyhydroxylated nitrones or N -hydroxy piperidines as glycosidase or glycosyltranferase inhibitors remains largely unknown.…”

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confidence: 99%

“…Finally, nitrone 8 and N -hydroxypiperidine 12 were deprotected using BCl 3 , affording the novel N -oxy iminosugars 14 and 15 in excellent yields of 97% and 91%, respectively (Scheme ) . These two compounds were assayed against a panel of 13 purified glycosidases .…”

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confidence: 99%

A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from d-Fructose

et al. 2009

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Ketonitrone 8 was prepared from D-fructose as an inexpensive starting material and was used in a stereoselective synthesis of 1-deoxymannojirimycin (DMJ, 4), of its previously unknown N-hydroxy analogue 15, and of the polyhydroxylated ketonitrone 14. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. Disappointingly, the polyhydroxylated nitrone 14 inhibited none of these enzymes. However, N-hydroxy-DMJ (15) exhibited a moderate and non-selective activity toward the snail beta-mannosidase EC 3.2.1.25.

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“…The 1,3-dipolar cycloaddition of nitrones in water has also been used to react two free sugar derivatives to produce pseudo-disaccharides, which bear imino-galactofuranose and galactofuranose units, in a 51% yield (Liautard et al, 2008). The reaction exploited the reactivity of water soluble nitrones with high enantioselectivity.…”

Section: 3-dipolar Cycloaddition In Watermentioning

confidence: 99%

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

et al. 2019

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The aim of this review is to provide an overview of green protocols for the organic synthesis of heterocycles via 1,3-dipolar cycloaddition. Particular attention has been devoted to the use of green solvents; reactions performed in ionic liquids, fluorinated solvents and water have been included. Also explored are several protocols that make use of catalyst-free reaction conditions, the use of microwave irradiation and activation by light exposure. Improvements over commonly used organic solvents will be underlined in order to highlight environmental protection aspects and enhancements in regio- and stereo-selectivity.

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Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water

Cited by 22 publications

References 44 publications

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from d-Fructose

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

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