Synthesis and Biological Evaluation of <i>S</i>‐Neofucopeptides as E‐ and P‐Selectin Inhibitors

Vargas, Ângelo; Molina, Lidia; Carmona, Ana T.; Ferrali, Alessandro; Lambelet, Martine; Spertini, Olivier; Robina, Inmaculada

doi:10.1002/ejoc.200800199

Cited by 25 publications

(9 citation statements)

References 56 publications

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“…For example, peptide motifs appended to fucose bind to P-selectin. These also exhibit selectivity for P-over E-selectin, which is consistent with the ability of the former to recognize an epitope encompassing a carbohydrate and a peptide backbone (Figure 8c) (112). As other examples of noncarbohydrate ligands, two small-molecule inhibitors of P-selectin were generated from a quinoline salicylic acid scaffold (Figure 8d ).…”

Section: Perturbation Of Protein-glycan Recognition With Monovalent Lsupporting

confidence: 64%

Chemical Approaches to Glycobiology

Kiessling

Splain

2010

Annu. Rev. Biochem.

208

176

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Glycans are ubiquitous components of all organisms. Efforts to elucidate glycan function and to understand how they are assembled and disassembled can reap benefits in fields ranging from bioenergy to human medicine. Significant advances in our knowledge of glycan biosynthesis and function are emerging, and chemical biology approaches are accelerating the pace of discovery. Novel strategies for assembling oligosaccharides, glycoproteins, and other glycoconjugates are providing access to critical materials for interrogating glycan function. Chemoselective reactions that facilitate the synthesis of glycan-substituted imaging agents, arrays, and materials are yielding compounds to interrogate and perturb glycan function and dysfunction. To complement these advances, small molecules are being generated that inhibit key glycan-binding proteins or biosynthetic enzymes. These examples illustrate how chemical glycobiology is providing new insight into the functional roles of glycans and new opportunities to interfere with or exploit these roles.

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Section: Perturbation Of Protein-glycan Recognition With Monovalent Lsupporting

confidence: 64%

Chemical Approaches to Glycobiology

Kiessling

Splain

2010

Annu. Rev. Biochem.

208

176

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“…Regio-and stereoselective alkoxide displacement of the exo-sulfonyl group produced 15 as the sole product with the introduction of an oxygen atom at the C-6 position. [18] Reductive removal of the sulfonyl group of 15 [19] and the inversion of the stereochemistry at C-6 would furnish the desired intermediate 7 for use in the metathesis reaction. Prior to these transformations, we resolved the two enantiomers of 15 by forming its ester from a chiral carboxylic acid.…”

Section: Resultsmentioning

confidence: 99%

A Formal Total Synthesis of Dysiherbaine and Neodysiherbaine A

Lee

Kim

et al. 2012

Eur J Org Chem

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A domino olefin metathesis reaction of 1‐alkyl‐3‐(allyloxy)‐7‐oxabicyclo[2.2.1]hept‐5‐enes 7 produced the fused bis(oxacyclic) structure for dysiherbaine and neodysiherbaine A (i.e., 6b) with the complete control of the relative stereochemistry at the quaternary carbon center and the ring junction of the dysiherbaine core skeleton. A formal total synthesis of dysiherbaine and neodysiherbaine A was achieved from 6b.

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“…As part of our continuing interest in the synthesis and applications of chiral furan amino acids,10c,15 we present herein the synthesis of the new furyl‐based cyclic peptide 1 (Figure 1, c) from D ‐xylose as inexpensive starting material and source of chirality. Cyclopeptide 1 decorated with a number of precisely positioned binding units present obvious advantages for the production of anion receptors.…”

Section: Introductionmentioning

confidence: 99%