Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase

Ghavami, Ahmad; Chen, Joan Jo-wen; Pinto, B. Mario

doi:10.1016/j.carres.2003.09.036

Cited by 25 publications

(12 citation statements)

References 35 publications

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“…Pinto and co‐workers designed ammonium, selenonium, and sulfonium ion mimics of Gal f phosphate, with a sulfate ion side chain (compounds 21 ) 73. 74 The sulfate ion was chosen for stability and because it is present in the known glycosidase inhibitors salacinol and kotalanol 75. The compounds were designed as transition state mimics for UGM but are only weak inhibitors (<45 % inhibition at 10 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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“…96 Using this information, Pinto et al synthesized transition-state mimics of the proposed oxocarbenium intermediate. 97,98 The synthesized sulfonium, ammonium, and selenium ions 83-88 ( Fig. 9) did not display a very strong inhibitory activity against UGM at a concentration of 10 mM.…”

Section: Inhibition Of the Mag Biosynthetic Pathwaymentioning

confidence: 93%

ChemInform Abstract: Recent Advances Toward the Inhibition of mAG and LAM Synthesis in Mycobacterium tuberculosis

et al. 2010

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“…Several UDP-analogues were also produced in order to inhibit this transferase and also the key UDP-galactopyranose mutase. [6][7][8][9][10][11][12] Considering recent knowledges related to the glycoconjugates part of Mycobacteria and Leishmania cell walls, some studies have focused on the biological impact of furanosyl-containing glycolipids. 2,[13][14][15][16][17][18][19] Until now, the best results were obtained using a bicatenar thiofuranoside as a potent biocide agent against M. tuberculosis.…”

Section: Synthesis and Biological Properties Of Galactofuranosyl-contmentioning

confidence: 99%

Synthesis and biological properties of galactofuranosyl-containing fluorescent dyes

Legentil

Belaz

Gangneux

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Two fluorescent galactofuranosides were synthesized and their biological activities evaluated on non-infected and Leishmania infected macrophages. Both tagged scaffolds were able to penetrate macrophages. Compared to the activity of the parent octyl galactofuranoside used as a reference, the fluorescein-conjugate showed altered biological properties while the rhodamine 6G one synergistically acted with the lipid chain to significantly increase antiparasitic activity.

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Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase

Cited by 25 publications

References 35 publications

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

Chemistry and Biology of Galactofuranose‐Containing Polysaccharides

ChemInform Abstract: Recent Advances Toward the Inhibition of mAG and LAM Synthesis in Mycobacterium tuberculosis

Synthesis and biological properties of galactofuranosyl-containing fluorescent dyes

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