Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis

Shahmohammadi, Sayeh; Faragó, Tünde; Palkó, Márta; Forró, Enikő

doi:10.3390/molecules27082600

Cited by 3 publications

(3 citation statements)

References 49 publications

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“…Fülöp et al directly converted this lactam into a chiral amino acid by enzymatic hydrolysis . Later, the same research group developed enzymatic kinetic resolution for the amide and ester of cis -ACPC. , The crystallization-based resolution methods can be an attractive alternative to the enzymatic approach. For example, N -Cbz- and N -Boc-protected cis -ACPC were resolved with dehydroabiethylamine and ephedrine, respectively, while the ethyl ester of N -4-fluorobenzylated cis -ACPC was resolved with mandelic acid .…”

Section: Resultsmentioning

confidence: 99%

Scalable Synthesis of All Stereoisomers of 2-Aminocyclopentanecarboxylic Acid─A Toolbox for Peptide Foldamer Chemistry

Kovalenko,

Rudzińska-Szostak,

Ślepokura

et al. 2024

J. Org. Chem.

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Although the construction of peptides with well-defined threedimensional structures and predictable functions, including biological activity, using conformationally constrained β-amino acids has been shown to be a very successful strategy, their broad application is limited by access to the appropriate building blocks. In particular, trans-and cis-stereoisomers of 2-aminocyclopentanecarboxylic acid (ACPC) are of high interest. The scalable synthesis of all four stereoisomers of Fmoc derivatives of ACPC is presented with NMR-based analysis methods for their enantiomeric purity.

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Section: Resultsmentioning

confidence: 99%

Scalable Synthesis of All Stereoisomers of 2-Aminocyclopentanecarboxylic Acid─A Toolbox for Peptide Foldamer Chemistry

Kovalenko,

Rudzińska-Szostak,

Ślepokura

et al. 2024

J. Org. Chem.

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“…In preliminary amidation experiments, the carboxylic acid and amine substrates (1:1 equiv) were dissolved in an organic solvent (1 mL) to provide a solution with a given concentration (46,92,460, or 920 mM). CALB (50 mg), molecular sieve (50 mg 3 Å size) to avoid the reversible hydrolysis reaction, and n-heptadecane (2 µL) as an internal standard were added to the above solution.…”

Section: General Procedures For Calb-catalyzed Amidationmentioning

confidence: 99%

“…Several lipases have been reported to exhibit high catalytic activity and stability in organic solvents [39,40]. In particular, Candida antarctica lipase B (CALB; Novozyme 435) prefers anhydrous conditions and it has been widely applied in esterification and hydrolysis studies [41][42][43][44][45][46]. CALB could also catalyze amidation reactions [47][48][49][50][51][52] when the amine is used as a nucleophile in anhydrous organic media.…”

Section: Introductionmentioning

confidence: 99%

A Sustainable Green Enzymatic Method for Amide Bond Formation

2023

Self Cite

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A sustainable enzymatic strategy for the preparation of amides by using Candida antarctica lipase B as the biocatalyst and cyclopentyl methyl ether as a green and safe solvent was devised. The method is simple and efficient and it produces amides with excellent conversions and yields without the need for intensive purification steps. The scope of the reaction was extended to the preparation of 28 diverse amides using four different free carboxylic acids and seven primary and secondary amines, including cyclic amines. This enzymatic methodology has the potential to become a green and industrially reliable process for direct amide synthesis.

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Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation

Juaristi

Avila‐Ortiz

2023

Synthesis

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Although known for millenia, it is only recently that mechanochemistry has caught serious attention by many chemists. Indeed, during the past 15 years an extraordinary number of reports concerning solid-state chemical transformations through grinding and milling techniques has been recorded. This short review discusses the circumstances that led to such renaissance, highlighting the present intense interest in so-called green chemistry, the enabling capacity of mechanochemistry to handle insoluble substrates, and the finding of the profound influence that additives can have on mechanochemically activated reactions. The core of this account focuses on salient developments in synthetic organic chemistry, especially in amino acid and peptide mechanosynthesis, the successful employment of mechanochemical activation in combination with asymmetric organocatalysis, the promising combination of mechanochemical activation with enzymatic and whole cell biocatalysis, and the remarkable achievement of multicomponent selective reactions via complex, multistep reaction pathways. The final section is dedicated to comment on some pending tasks in the area, such as scaling-up of milling processes to be of practical use in the chemical industry, the requirement of easier and more efficient control of reaction parameters and monitoring devices, and consequently the careful analysis of additional procedures for a proper understanding of mechanochemical phenomena.

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Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis

Cited by 3 publications

References 49 publications

Scalable Synthesis of All Stereoisomers of 2-Aminocyclopentanecarboxylic Acid─A Toolbox for Peptide Foldamer Chemistry

Scalable Synthesis of All Stereoisomers of 2-Aminocyclopentanecarboxylic Acid─A Toolbox for Peptide Foldamer Chemistry

A Sustainable Green Enzymatic Method for Amide Bond Formation

Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation

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