Controlled Solid Phase Peptide Bond Formation Using <i>N</i>-Carboxyanhydrides and PEG Resins in Water.

Marco, Rossella De; Tolomelli, Alessandra; Greco, Arianna; Gentilucci, Luca

doi:10.1021/sc400058r

Cited by 29 publications

(24 citation statements)

References 39 publications

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“…In perspective, the peptide‐functionalized nanostructured systems described herein could be utilized to the rapid detection of markers of inflammatory diseases in patients, that is, integrin α 4 β 1 expressed in immune cells, that shows the promise of a simple and accessible test to be carried out in biological samples, when used in any appropriate clinical setting aimed at monitoring the course of the disease and the efficacy of the therapy. With the view of the development of a prototype, studies are in progress in our laboratory to optimize an environmentally sustainable procedure for the synthesis of the peptidomimetics and their anchoring under green chemistry conditions …”

Section: Discussionmentioning

confidence: 99%

Selective detection of α4β1 integrin (VLA‐4)‐expressing cells using peptide‐functionalized nanostructured materials mimicking endothelial surfaces adjacent to inflammatory sites

et al. 2018

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Persistent accumulation of immune cells mediated by α4β1 integrin (VLA-4) is a hallmark of the inflammatory diseases and of chronic inflammation observed in the affected tissues of autoimmune diseases. Aiming at exploring new methods for monitoring the course of the inflammatory processes, we designed the first peptide-functionalized nanostructured devices capable to mimic the high-density multivalency binding between the α4β1 integrin-expressing cells and the ligands overexpressed on the endothelial surfaces, in the proximity of the sites of inflammation. Specifically, we describe the first examples of monolayers constituted by dye-loaded zeolite L crystals, coated with α4β1 integrin peptide ligands, and we analyze the adhesion of model Jurkat cells in comparison to non-α4β1 integrin-expressing cells. In particular, the peptidomimetic diphenylurea-Leu-Asp-Val-diamine allows significant and selective detection of α4β1 integrin-expressing Jurkat cells, after very rapid incubation time, supporting the possible implementation in a diagnostic device capable to detect the desired cells from biological fluids, obtainable from patients in a noninvasive way.

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Section: Discussionmentioning

confidence: 99%

Selective detection of α4β1 integrin (VLA‐4)‐expressing cells using peptide‐functionalized nanostructured materials mimicking endothelial surfaces adjacent to inflammatory sites

et al. 2018

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“…PS resins usually swell well mainly in CH 2 Cl 2 , whereas PEG resins swell well in various solvents . The introduction of PEG resins, such as ChemMatrix® allowed peptide synthesis to be carried out even in water and also facilitated the synthesis of larger peptides …”

Section: Solid‐phase Peptide Synthesismentioning

confidence: 99%

“… Chemical structures of some of the peptides synthesized in the literature by using greener approaches. Analogs of Leu‐enkephalin were also synthesized by exchanging the Gly‐Gly moiety shown in red with the Aib residue …”

Section: Attempts To Make a Greener Protocolmentioning

confidence: 99%

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Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Varnava

Sarojini

2019

Chemistry An Asian Journal

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To date, the synthesis of peptides is concurrent with the production of enormous amounts of toxic waste. DMF, CH2Cl2, and NMP are three of the most toxic organic solvents used in chemical synthesis and are the most common solvents used for peptide synthesis. Additionally, concerns about the hepatotoxicity caused by exposure to DMF and from the toxic and allergenic nature of additives used in peptide synthesis necessitates the need for a green, environmentally friendly, and safer protocol for peptide synthesis. This review summarizes the current literature on green solid‐phase peptide synthesis successes and challenges encountered. The review concludes with suggestions for future research towards a simple and efficient green peptide synthesis protocol.

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“…This ultimately results in a simplified reaction scheme and a highly atom economical synthesis of a peptide bond, unlike traditional approaches to peptide synthesis. The use of NCAs for the solid-supported synthesis of peptides was first reported by De Marco et al [27]. The NCA derivatives were first prepared in almost quantitative yields by treatment of the relevant amino acid with triphosgene using a solvent free, microwave assisted synthesis (Fig.…”

Section: N-carboxyanhydridesmentioning

confidence: 99%

Greener solvents for solid-phase organic synthesis

Lawrenson

2017

Pure and Applied Chemistry

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Solid-phase organic synthesis is an essential method for the rapid synthesis of complex biological structures and libraries of small organic molecules. However, it is often associated with the use of large quantities of problematic solvents for the removal of excess reagents and reaction by-products. Given that solvent will often be the biggest contributor to waste generated in the average pharmaceutical/fine-chemical process, its exchange for a more desirable alternative often presents the biggest gains in terms of reducing environmental impact. This review aims to explore recent approaches to performing solid-phase organic synthesis, and associated solid-phase peptide synthesis, in neoteric solvents and reaction media that present greener alternatives.

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Controlled Solid Phase Peptide Bond Formation Using N-Carboxyanhydrides and PEG Resins in Water.

Cited by 29 publications

References 39 publications

Selective detection of α4β1 integrin (VLA‐4)‐expressing cells using peptide‐functionalized nanostructured materials mimicking endothelial surfaces adjacent to inflammatory sites

Selective detection of α4β1 integrin (VLA‐4)‐expressing cells using peptide‐functionalized nanostructured materials mimicking endothelial surfaces adjacent to inflammatory sites

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Greener solvents for solid-phase organic synthesis

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