Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery

Ziora, Zyta M.; Wimmer, Norbert; New, R. R. C.; Skwarczynski, Mariusz; Tóth, István

doi:10.1016/j.carres.2011.03.019

Cited by 8 publications

(4 citation statements)

References 34 publications

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“…Coupling constants were provided in Hz. 13 C spectra were measured at 100.62 MHz and 125.77 MHz and referenced to CDCl 3 (77.0 Hz), CD 3 OD (49.0 Hz) or Acetone-d 6 (30.5 Hz). Homo-and heteronuclear 2D NMR spectroscopy was performed using Bruker standard software.Thin layer chromatography (TLC) was performed on Merck pre-coated aluminum sheets (Silica Gel 60F254); spots were detected by spraying with H 2 SO 4 .…”

Section: Resultsmentioning

confidence: 99%

“…However, an extensive aggregation was also observed. The tendency to form large aggregates can be explained by the relatively high hydrophobicity of synthesized amphiphiles [13,14]. To obtain more uniform particles, the nanoparticle might be selfassembled by dialysis of a solution of the lipopeptides in organic solvent against water [15,16].…”

Section: Introductionmentioning

confidence: 99%

“…ITC is a sensitive, routine method which allows determining the critical micelles/aggregates concentration (CMC/CAC) and provides access to thermodynamic parameters such as enthalpy (ΔH), entropy (ΔS) and Gibbs free energy (ΔG) of micellization/aggregation [12,13]. Titration of concentrated mixture of compounds 1a-d or 2a-c into water allowed disaggregation and formation of new particles (aggregates/micelles).…”

Section: Introductionmentioning

confidence: 99%

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Lipopeptides for the Fragment-Based Pharmaceutics Design

Ziora¹,

Wimmer²,

New³

et al. 2012

IJOC

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This paper describes the synthesis of peptide fragments for use in a new type of combinatorial discovery technology, in which the building blocks are brought together by non-covalent interactions, rather than direct chemical bonding. The building blocks of interest-in this case different amino acids-are converted to amphiphiles by attachment to lipid tails. The amphiphiles, when mixed together in aqueous phase, are designed so that they aggregate spontaneously to form micelles. The building blocks form the headgroups of each of the amphiphiles, and these headgroups cover the surface of the micelle in a dynamic close-packed fluid mosaic array. These building blocks come together so closely that twoor three-dimensional structures are created on the surface of the micelles, and these can be screened in biological assays to find out which combination of building blocks is able to elicit a biological response. Lipopeptides consisting of two residues of lipoamino acid and other amino acids moieties have been designed, synthesized, characterized and the ability of these constructs to form supra-molecular assemblies is demonstrated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Lipopeptides for the Fragment-Based Pharmaceutics Design

Ziora¹,

Wimmer²,

New³

et al. 2012

IJOC

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“…In one of the studies described here, the pool of amino acids has been supplemented by sugars; when these constitute the head groups of the amphiphile, they are bound to the rest of the peptide chain via an ester linkage, usually through the side chain of a terminal glutamic acid residue. A description of the synthesis of these amphiphiles, and some properties of the resultant micelles are given in papers published by the authors [2,3].…”

Section: Introductionmentioning

confidence: 99%

Use of Mixed Micelles for Presentation of Building Blocks in a New Combinatorial Discovery Methodology: Proof-of-Concept Studies

et al. 2013

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Abstract:We describe a new method of combinatorial screening in which building blocks, instead of being linked together chemically, are placed on the surface of nanoparticles. Two-or three-dimensional structures form on the surface of these particles through the close approach of different building blocks, with sufficient flexibility to be able to adapt and interact with putative binding sites in biological systems. The particles assemble without the need for formation of chemical bonds, so libraries comprised of many structures can be prepared rapidly, with large quantities of material available for testing. Screening methods can include solid and solution-phase binding assays, or tissue culture models, for example looking for structures which can change the behaviour of cells in a disease-modifying manner.

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