The synthesis of d-C-mannopyranosides

Choumane, Mariam; Banchet, Aline; Probst, Nicolas; Gérard, Stéphane; Plé, Karen; Haudrechy, Arnaud

doi:10.1016/j.crci.2010.05.015

Cited by 17 publications

(19 citation statements)

References 272 publications

(269 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The C -linked analogue 6 , having a C-O-C bond shorter, deserves some specific comments on its own because of the controversial arguments about the preferred conformational states of this family of glycomimetics. Indeed, several literature cases argued for the fact that C- linked α-D-mannopyranosides do not exist preferentially in the “usual” 4 C 1 chair conformations, at least for simple aglycones [10,38,39,40,41]. As already shown by us with O -linked allyl α-D-mannopyranoside [10], the 4 C 1 conformation was the most stable form with the inverted 1 C 4 chair being next in line with a difference of 8.10 kcal/mole difference.…”

Section: Resultsmentioning

confidence: 99%

Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH

et al. 2019

View full text Add to dashboard Cite

A set of three mannopyranoside possessing identical 1,1′-biphenyl glycosidic pharmacophore but different aglyconic atoms were synthesized using either a palladium-catalyzed Heck cross coupling reaction or a metathesis reaction between their corresponding allylic glycoside derivatives. Their X-ray structures, together with their calculated 3D structures, showed strong indicators to explain the observed relative binding abilities against E. coli FimH as measured by a improved surface plasmon resonance (SPR) method. Amongst the O-, C-, and S-linked analogs, the C-linked analog showed the best ability to become a lead candidate as antagonist against uropathogenic E. coli with a Kd of 11.45 nM.

show abstract

Section: Resultsmentioning

confidence: 99%

Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH

et al. 2019

View full text Add to dashboard Cite

show abstract

“…20−23 The abundance of new data can be judged from a recent review, which covers the synthesis of C-(D-mannopyranosyl)-alkanes, -arenes, and -hetarenes. 24 Naturally occurring compounds of the C-glycosylated arene type have been reviewed, with focus on structure, activity, synthesis, and biosynthesis, 25 and this applies also for bioactive C-glycosyl compounds from bacterial secondary metabolism. 26 Glycomimetics of the C-glycosyl arene type were designed as selectin antagonists, and tested in view of their biological and pharmacological evaluation.…”

Section: Introductionmentioning

confidence: 99%

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

View full text Add to dashboard Cite

This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes. A classification of the preparative routes to these synthetic targets according to methodologies and compound categories is provided. Several of these compounds, regardless of their natural or synthetic origin, display antidiabetic properties due to enzyme inhibition (glycogen phosphorylase, protein tyrosine phosphatase 1B) or by inhibiting renal sodium-dependent glucose cotransporter 2 (SGLT2). The latter class of synthetic inhibitors, very recently approved as antihyperglycemic drugs, opens new perspectives in the pharmacological treatment of type 2 diabetes. Various compounds with the C-glycopyranosyl (het)arene motif were subjected to biological studies displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.

show abstract

“…As stated above, [33][34][35][36][37][38] there are several papers indicating that C-linked α-D-mannopyranosides can exist in conformations other than those observed for the corresponding O-linked derivatives, normally seen as 4 C1 conformers. Obviously, changing bond lengths, bond angles, torsion angles, and conformations would have a detrimental effect upon binding of antagonists to E. coli FimH.…”

Section: Resultsmentioning

confidence: 94%

“…1,11 However, in the case of C-linked mannopyranosides and those possessing hydrophobic/aryl aglycones in particular, there have been very few studies on their precise conformational analyses. 33 This is particularly important given the propensity of C-mannopyranosides to exist in diverse conformations ( 4 C1, 1 C4, 2 S0, and 0 S2). [34][35][36][37][38] This paper describes practical approaches to the syntheses of C-allyl α-D-mannopyranoside, which is a versatile building block toward E. coli FimH antagonists.…”

Section: Introductionmentioning

confidence: 99%

Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. coli FimH ligands

Mousavifar¹,

Vergoten²,

Roy³

2018

Arkivoc

View full text Add to dashboard Cite

C-Allyl -D-mannopyranosides were prepared via a variety of routes to determine an optimal route to the anomers. The relative conformational energies of the key intermediate was evaluated by molecular modeling which showed the conventional 4 C1 chair conformation to be the lowest energy conformer. This finding was also confirmed by NMR and X-ray crystallography. The perbenzoylated C-allyl mannoside was also converted into 1,1'-biphenyl analogues using a palladium-catalyzed Heck reaction. Two of the resulting minor reaction products were co-crystallized with the uropathogenic E. coli FimH. Alternatively, the KD of the major and expected Heck product was in the low nM range as measured by SPR. Crystal data showed that the C-linked derivatives efficiently bind in the FimH binding cavity near the so-called hydrophobic tyrosine gate.

show abstract

The synthesis of d-C-mannopyranosides

Cited by 17 publications

References 272 publications

Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH

Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. coli FimH ligands

Contact Info

Product

Resources

About