Mechanoenzymatic peptide and amide bond formation

Hernández, José G.; Ardila‐Fierro, Karen J.; Crawford, Deborah E.; James, Stuart L.; Bolm, Carsten

doi:10.1039/c7gc00615b

Cited by 89 publications

(69 citation statements)

References 58 publications

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“…Indeed, liquid reaction mixtures enable efficient agitation when using a conventional batch reactor equipped with either magnetic stirring bar or impeller, and automated handling such as pumping and filtration. Since Lamaty and co-workers have shown in their seminal work that peptide synthesis could be performed in a ball-mill (BM) [9], various solvent-free or solvent-less peptide synthesis strategies have been developed [10][11][12][13][14][15][16][17]. While these approaches enable to circumvent the use of toxic solvents and bases [18][19][20], no comparison between ballmilling and conventional approaches was performed, discussed and communicated.…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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

“…[53] In contrast, the use of the lipase CALB selectively catalyzed the acetylation of the primary hydroxy group in 48 a,a ffording mono-acetylated product 50 a in 93 %y ield (Scheme 13). [56] In particular, papain (peptide hydrolase EC 3.4.22.2) provedh ighly active to couple N-protected a-aminoe sters 51 and amino amides 34.B all-milling of am ixture of 51 and 34 in the presence of papain powder,N a 2 CO 3 ·10 H 2 O and l-cysteine as the activator gave as eries of dipeptides in high yields (Scheme 14 a). Inter- Scheme12.…”

Section: Catalysis By Peptides and Enzymes Under Mechanochemical Condmentioning

confidence: 99%

“…[56] Building on this previous work, the same research team studied the mechanoenzymatic homo-oligomerization of amino acids in the ball mill. However, papain was shownt oeffectively transfer N-protected a-amino esters bearing side chains of different bulkiness and hydrophobicity to the acyl acceptor.…”

Section: Catalysis By Peptides and Enzymes Under Mechanochemical Condmentioning

confidence: 99%

From Synthesis of Amino Acids and Peptides to Enzymatic Catalysis: A Bottom‐Up Approach in Mechanochemistry

2018

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Recently, chemical reactions induced or facilitated by mechanical energy have gained recognition in diverse areas of chemical synthesis. In particular, mechanosyntheses of amino acids and short peptides, along with their applications in catalysis, have revealed the high degree of stability of peptide bonds in environments of harsh mechanical stress. These observations quickly led to the recent interest in developing mechanochemical enzymatic reactions. Experimentally, manual grinding, ball-milling techniques, and twin-screw extrusion technology have proven valuable to convey mechanical forces into a chemical synthesis. These practices have enabled the establishment of more sustainable alternatives for chemical synthesis by reducing the use of organic solvents and waste production, thereby having a direct impact on the E-factor of the chemical process. In this Minireview, the series of events that allowed the development of mechanochemical enzymatic reactions are described from a bottom-up perspective.

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“…[28] Scheme 3. [37] [28] Furthermore, the synthesis of the isopropyl analogue could also be performed under the same conditions; in solution, high temperatures and long reaction times are necessary.…”

Section: Mechanochemistry In Organic Synthesismentioning

confidence: 99%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

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Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

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Mechanoenzymatic peptide and amide bond formation

Abstract: Mechanochemical chemoenzymatic peptide and amide bond formation catalysed by papain was studied by ball milling.

Cited by 89 publications

References 58 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?

From Synthesis of Amino Acids and Peptides to Enzymatic Catalysis: A Bottom‐Up Approach in Mechanochemistry

Organic Synthesis without Conventional Solvents

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