Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

Desvergnes, Stéphanie; Desvergnes, Valérie; Martin, Olivier R.; Itoh, Kenji; Liu, Hung Wen; Py, Sandrine

doi:10.1016/j.bmc.2007.06.059

Cited by 46 publications

(13 citation statements)

References 48 publications

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“…Additionally, the same group used a [3+2] dipolar cycloaddition to synthesize a pyrrolidine‐ and phosphonate‐containing UDP‐Gal f mimic (compound 15 ),67 though no biological data were reported for this compound. Similarly, several other pyrrolidine analogues were synthesized by Desvergnes et al,68 and the best of these compounds (compound 16 ) displayed <35 % inhibition of UGM at 25 m M .…”

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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“…[107] This synthetic strategy was applied to other ppolyhydroxylated nitrones and the resulting hydroxylamines were used as valuable synthetic intermediates in the preparation of compounds of biological interest such as 1,4-imino-D-galactitols. [108] Scheme 29…”

Section: Scheme 25mentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

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This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

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“…9) that produced weak inhibition (0–11%) at 2 M 100. Martin and co‐workers prepared UDP‐Gal f analogs and transition‐state analogs 92–98 built around a 1,4‐dideoxy‐1,4‐imino‐ D ‐galactitol 101–103. The inhibitory activities of the various galactitol‐based inhibitors against UGM are shown in Figure 9.…”

Section: Inhibition Of the Mag Biosynthetic Pathwaymentioning

confidence: 99%

Recent advances toward the inhibition of mAG and LAM synthesis in Mycobacterium tuberculosis

Umesiri

Sanki

Boucau

et al. 2010

Medicinal Research Reviews

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Drug-resistant forms of Mycobacterium tuberculosis (M. tuberculosis) are increasing worldwide, underscoring the need to develop new drugs to treat the disease. One of the factors that make tuberculosis difficult to treat is the unique architecture of the mycobacterial cell wall. In this review, we catalogue the enzymes involved in the synthesis of the mycolylarabinogalactan (mAG), a key structural component of the mycobacterial cell wall. In addition, we review the enzymes required for the synthesis of the related lipoarabinomannan (LAM), a structure that possesses immunomodulatory properties. The integrity of the mAG and LAM is critical to the viability of mycobacteria, and many of the established antimycobacterial agents target enzymes critical to the synthesis of the mAG and LAM. Recently, new enzymes catalyzing synthetic steps in the synthesis of the mAG and LAM have been characterized and their substrate specificity determined. In this report, we review recent efforts to characterize the enzymes involved in mAG and LAM synthesis and describe the compounds used to inhibit the enzymes or characterize their catalytic activity.

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Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

Cited by 46 publications

References 48 publications

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Recent advances toward the inhibition of mAG and LAM synthesis in Mycobacterium tuberculosis

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