The greening of peptide synthesis

Lawrenson, Stefan B.; Arav, Roy; North, Michael

doi:10.1039/c7gc00247e

Cited by 160 publications

(135 citation statements)

References 80 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: 95%

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: 95%

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

“…[83] As they are highly specific in the interaction with their in vivo targets while causing few negative side effects, their role in the future of drug discoveryi sf oreseen to be even higher. [85,86] Thus, reprotoxic polar aprotic solvents, such as dimethylformamide (DMF), dimethylacetamide (DMA), and N-methyl pyrrolidone (NMP), are commonly used, although all of them are classified as substances of very high concern( SVHCs) under Registration, Evaluation, Authorization and restrictiono fC hemicals (REACH), indicating that their use will be restricted in the near future. In economic terms, the overall peptidic drugs market in 2015 was estimated to be around US$ 14.1 billion, and was predicted to grow up to aroundUS$ 25.4 billion by 2018.…”

Section: Other Emerging Applications Of Cpme In Bioeconomy:c Hromatogmentioning

confidence: 99%

Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Gonzalo

Alcántara

Marı́a³

2019

ChemSusChem

122

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The quest for sustainable solvents is currently a matter of intense research and development, as solvents significantly contribute heavily to the waste generated by chemical industries. Cyclopentyl methyl ether (CPME) is a promising eco‐friendly solvent with valuable properties such as low peroxide formation rate, stability under basic and acidic conditions, and relatively high boiling point. This Review discusses the potential use of CPME for applications in biotechnology (e.g., biotransformations, as solvent or cosolvent), biorefineries, and bioeconomy (e.g., for furan synthesis or as an extractive agent in liquid–liquid separations), as well as for other purposes, such as chromatography or peptide synthesis. Although CPME is currently produced by petrochemical means with a remarkably high atom economy, its biogenic production can be envisaged from substrates such as cyclopentanol or cyclopentanone, which can be derived from furfural or from (bio‐based) adipic acid, respectively. The combination of the promising properties of CPME as a (co)solvent with a future (economic) biogenic origin would be advantageous for setting strategies aligned with the sustainable chemistry principles.

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“…Lawrenson et al [36] have also recently contributed to the field of alternative organic solvents for SPOS in the use of cyclic carbonates for SPPS. Cyclic carbonates have been highlighted as highly promising replacements for conventional polar aprotic solvents, due to the fact they are non-toxic, biodegradable and produce no NO x or SO x upon incineration.…”

Section: Alternative Organic Solventsmentioning

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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The greening of peptide synthesis

Abstract: Both couplings and deprotections for solution- and solid-phase peptide synthesis can be carried out in the polar aprotic solvent propylene carbonate.

Cited by 160 publications

References 80 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?

Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Greener solvents for solid-phase organic synthesis

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