Greener solvents for solid-phase synthesis

Lawrenson, Stefan B.; North, Michael; Peigneguy, Fanny; Routledge, Anne

doi:10.1039/c6gc03147a

Cited by 98 publications

(82 citation statements)

References 54 publications

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“…Of note, various research groups have screened greener solvents for SPPS [35][36][37][38]. The results issuing from these studies indicate that a reduction of the cumulative Number of Hazard Phrases in both the coupling and deprotection steps may be accessible by choosing more appropriate solvents than DMF.…”

Section: Comparison Based On the Environmental Impactmentioning

confidence: 96%

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

Maurin¹,

Verdié²,

Subra³

et al. 2017

Beilstein J. Org. Chem.

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While presenting particularly interesting advantages, peptide synthesis by ball-milling was never compared to the two traditional strategies, namely peptide syntheses in solution and on solid support (solid-phase peptide synthesis, SPPS). In this study, the challenging VVIA tetrapeptide was synthesized by ball-milling, in solution, and on solid support. The three strategies were then compared in terms of yield, purity, reaction time and environmental impact. The results obtained enabled to draw some strengths and weaknesses of each strategy, and to foresee what will have to be implemented to build more efficient and sustainable peptide syntheses in the near future.2087

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Section: Comparison Based On the Environmental Impactmentioning

confidence: 96%

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

Maurin¹,

Verdié²,

Subra³

et al. 2017

Beilstein J. Org. Chem.

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show abstract

“…Racemization of the activated amino acids in PC was negligible and the methodology was applied to the synthesis of the nonapeptide bradykinin (an inflammatory mediator; Figure ) . The authors have also reported extensive and in‐depth studies screening different green solvents and their ability to swell the most commonly used resins . Interestingly though, the authors report that the piperidine cocktail needs to be freshly prepared, but no data on the stability of piperidine in PC are given.…”

Section: Attempts To Make a Greener Protocolmentioning

confidence: 99%

“…[49] The authors have also reported extensivea nd in-depths tudies screening different green solvents and their ability to swell the most commonly used resins. [50] Interestingly though, the authors report that the piperidine cocktail needs to be freshly prepared, but no data on the stability of piperidine in PC are given.T he most recent report on the greening of peptide synthesis comes from Novartis Pharmaceutical. [51] Scientists at Novartis screened as eries of solvents and provided in-depthi nformationr egarding all challenging steps of the synthesis.…”

Section: Greener and Safer Solventsmentioning

confidence: 99%

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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“…[19] This is in contrast to at raditional ketone,s uch as acetone, that tend to exist predominantly in the ketone form in aqueouss olutions.T he equilibrium also can be shifted in the presence of 1,2-diols, which form cyclic acetals outo f the ketone moiety. [49] Hoping to take advantage of the strong solvency power of Cyrene, anumber of research groups have investigated its use as as olvent for synthetic transformations. An increased understandingo ft his equilibrium-specifically regarding the pH, temperature, and Scheme4.Nucleophilic additionst oC yrene (2).…”

Section: Use Of Cyrene As Abio-available Solventmentioning

confidence: 99%

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

2018

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The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class of solvents is the dipolar aprotics, which include N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP). In addition to being derived from non-renewable resources, these solvents are also under increased regulatory pressures that will limit their industrial applications. This Concept concerns the bio-available solvent Cyrene (dihydrolevoglucosenone) as a potential replacement for toxic dipolar aprotic solvents. An emphasis is placed on examining the strengths and weaknesses of Cyrene as a solvent and is accomplished by looking at the synthesis, derivatization, and application in synthetic protocols of Cyrene. With respect to the Twelve Principles of Green Chemistry, this Concept describes a bio-available solvent that should have a disruptive effect on the use of traditional industrial dipolar aprotic solvents.

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Greener solvents for solid-phase synthesis

Abstract: The use of a range of green solvents to swell a diverse range of resins used in solid-phase synthesis is investigated.

Cited by 98 publications

References 54 publications

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

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

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

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