CHAPTER 6. Amino Acids and Peptides in Ball Milling

Métro, Thomas‐Xavier; Colacino, Evelina; Martínez, Jean; Lamaty, Frédéric

doi:10.1039/9781782621980-00114

Cited by 15 publications

(14 citation statements)

References 35 publications

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“…In organic chemistry, amino acids and short peptides are not only known for being stable under automated ball milling conditions during their preparation [ 4 ], but also when applied as catalysts to perform stereoselective transformations [ 5 – 7 ]. Encouraged by these facts, we recently investigated the resilience of enzymes under ball milling conditions.…”

Section: Introductionmentioning

confidence: 99%

Selective enzymatic esterification of lignin model compounds in the ball mill

Weißbach¹,

Dabral²,

Konnert³

et al. 2017

Beilstein J. Org. Chem.

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A lipase-catalyzed esterification of lignin model compounds in the ball mill was developed combining the advantages of enzyme catalysis and mechanochemistry. Under the described conditions, the primary aliphatic hydroxy groups present in the substrates were selectively modified by the biocatalyst to afford monoesterified products. Amongst the tested lipases, CALB proved to be the most effective biocatalyst for these transformations. Noteworthy, various acyl donors of different chain lengths were tolerated under the mechanochemical conditions.

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Section: Introductionmentioning

confidence: 99%

Selective enzymatic esterification of lignin model compounds in the ball mill

Weißbach¹,

Dabral²,

Konnert³

et al. 2017

Beilstein J. Org. Chem.

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“…This strategy is called solvent‐assisted grinding (LAG) . In this context, a recent study by Porte and co‐workers[7d] recommends the use of EtOAc and γ‐valerolactone as green additives in α‐peptide mechanosynthesis. Therefore, we examined to use EtOAc as liquid additive in the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…In this regard, in recent years several green strategies in organic chemistry that employ non‐traditional energy sources, such as ultrasound irradiation, microwave, and high‐speed ball‐milling (HSBM), have been developed . The latter technique, also known as mechanochemistry, has proven to be a viable green alternative for the synthesis of amides and peptides under solvent‐free conditions or liquid‐assisted grinding (LAG), achieving good yields in short reaction times, reducing production costs, and minimizing waste of valuable chemicals …”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis of Dipeptides Using Mg‐Al Hydrotalcite as Activating Agent under Solvent‐Free Reaction Conditions

Landeros

Juaristi

2017

Eur J Org Chem

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Given the high demand for green and sustainable synthetic methods for the formation of amides and peptidic bonds, herein we report the efficient, solvent‐free mechanochemical synthesis of dipeptides from N‐protected amino acids and amino acid methyl ester hydrochlorides in the presence of 1‐hydroxybenzotriazole (HOBt) and N‐ethyl‐N′‐[3‐(dimethylamino)propyl]carbodiimide hydrochloride (EDC) as coupling reagents, and using Mg‐Al hydrotalcite‐like minerals as green activating agent. From commercial Mg‐Al hydrotalcite (HT‐S), we obtained its calcined (HT‐C) and reconstructed (HT‐R) modifications, which were evaluated as activating heterogeneous bases in amidation reactions, replacing commonly used toxic and/or corrosive bases (e.g., NEt3, iPr2NEt and NaOH). As a practical application of this strategy, various α,α‐, α,β‐ and β,β‐dipeptides were prepared in good to excellent yields. Under optimized reaction conditions (vibrating mill at 25 Hz for 75 min) HT‐S and HT‐R showed higher activity (89 % yield of the desired peptide) compared with HT‐C (57 % yield). The present protocol offers several advantages, including the use of readily available reagents and inexpensive materials, easy workup, simple recovery and recyclability of the hydrotalcite activator, and short reaction times.

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“…[108] Mechanochemical reactions, which proceed either in the absence or with very small quantities of al iquid additive, present an ovel approacht oc ontrol the reactivity of proteases.M echanochemicaln onenzymatic solid-state approaches ford ipeptide and oligopeptide synthesis [109][110][111][112][113] have been shown to surpasss olution synthesis and even SPPS in terms of shorterr eaction times, improved product purity and reduced environmental impact. [114,115]…”

Section: Protease-catalyzed Mechanoenzymatic Reactions By Ball Millinmentioning

confidence: 99%

Mechanoenzymatic Transformations in the Absence of Bulk Water: A More Natural Way of Using Enzymes

2019

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Mechanochemical enzymatic reactions without bulk water have emerged as a low‐waste and efficient method to access useful chemicals and to depolymerize biomass components in a single step. This emergent mechanoenzymatic reaction strategy is able to take advantage of the stereospecificity, regio‐ and stereoselectivity, as well as renewability of enzymes, while avoiding bulk solvents, offering the opportunity to control the direction of the reaction, bypassing reactant solubility issues, and enabling reactions with water‐sensitive substrates or products. Enzymes are traditionally used in dilute aqueous solution, which is quite different from their crowded, water‐depleted natural environment. This review outlines recent work which demonstrates that enzymes can be equally or even more efficient under mechanochemical conditions, without bulk aqueous or organic solvent.

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CHAPTER 6. Amino Acids and Peptides in Ball Milling

Cited by 15 publications

References 35 publications

Selective enzymatic esterification of lignin model compounds in the ball mill

Selective enzymatic esterification of lignin model compounds in the ball mill

Mechanochemical Synthesis of Dipeptides Using Mg‐Al Hydrotalcite as Activating Agent under Solvent‐Free Reaction Conditions

Mechanoenzymatic Transformations in the Absence of Bulk Water: A More Natural Way of Using Enzymes

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