One‐Step Biocatalytic Synthesis of Sustainable Surfactants by Selective Amide Bond Formation**

Lubberink, Max; Finnigan, William; Schnepel, Christian; Baldwin, Christopher; Turner, Nicholas J.; Flitsch, Sabine L.

doi:10.1002/ange.202205054

Cited by 7 publications

(9 citation statements)

References 36 publications

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“…[81] The MmCAR A-domain alone (i. e. MmCAR Δ647-1175 ) was then applied for the synthesis of amino-amides [83] and Nalkanoyl-N-methylglucamides. [84] In case the amine donor is present on the carboxylate substrate itself, CARs can mediate lactam formation as shown first for MaCAR2 [85] and then for SruCAR and its phosphopantetheinyl attachment site mutant SruCAR S702A . [86] Likewise, MmCAR was also able to catalyze esterification of a variety of carboxylic acids and alcohols, albeit with lower yield compared to amidation.…”

Section: Promiscuous Reactions Catalyzed By Cars or Car Domainsmentioning

confidence: 99%

Biocatalytic Carboxylate Reduction – Recent Advances and New Enzymes

Winkler

Ling

2022

ChemCatChem

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Carboxylate reductases (CARs) are valuable catalysts for the selective one‐step reduction of carboxylic acids to their corresponding aldehydes. In recent years, numerous new CARs have been made available, studied and applied in the context of biocatalytic syntheses. The preparation of aldehydes as end products for the flavor and fragrance sector and the integration of CARs in cascade reactions with aldehydes as the key intermediates represent the two major fields of applications. This review gives a comprehensive overview of the current toolbox of recombinant CARs and their numerous carboxylate substrates. Non‐natural functions of CARs are highlighted and recent insight into the structure‐function relationship of CARs are summarized.

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Section: Promiscuous Reactions Catalyzed By Cars or Car Domainsmentioning

confidence: 99%

Biocatalytic Carboxylate Reduction – Recent Advances and New Enzymes

Winkler

Ling

2022

ChemCatChem

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“…Several enzymatic methods for amide-bond formation have been summarized in two recent reviews. 8 9 Enzymes that catalyze this reaction can be roughly divided into two groups. The first group consists of ATP-dependent enzymes that use ATP to activate the carboxylic acid.…”

Section: Table 1 Reactions Studied With Peste_i208a_l20...mentioning

confidence: 99%

Enzymatic Synthesis of Hydroxycinnamic Acid Amides in Water Using the Promiscuous Hydrolase/Acyltransferase PestE from Pyrobaculum calidifontis VA1

Bornscheuer,

Baumert,

Terholsen

et al. 2024

Synlett

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Hydroxycinnamic acid amides are believed to have antioxidant, antidiabetic, cytotoxic, anticancer, neuroprotective, and antiinflammatory properties, making them interesting target molecules for potential applications in the food, cosmetics, and pharmaceutical industries. Here, we describe the synthesis of hydroxycinnamic acid amides starting from hydroxycinnamic acid esters and the corresponding amines by using variants of the promiscuous hydrolase/acyltransferase from Pyrobaculum calidifontis VA1 (PestE) in water as a solvent. Up to 97% conversion within two hours at 60 °C was achieved with methyl ferulate and tyramine as substrates. This is a promising, environmentally friendly alternative strategy to established chemical synthesis routes or enzymatic methods using lipases in nonaqueous organic solvents.

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“…Biocatalysis has emerged as a crucial tool in modern organic synthesis, finding applications not only in academia but also in the chemical and pharmaceutical industries [59] . Recently, there has been a comprehensive review of the use of biocatalysis in amide synthesis [1l] …”

Section: Synthesis Of Amides From Carboxylic Acidsmentioning

confidence: 99%

“…These methods include C−H amidation using acyl nitrenes, [10] Ullmann‐type reactions with amides, or aldol‐type reactions using amide enolate surrogates [11] . However, this review does not cover methods specifically targeting amide bonds in peptide synthesis, as recent reviews of enzymatic approaches [1l,12] and highlighting peculiar problems in this chemistry have already been published [13]…”

Section: Introductionmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out of the thirty‐seven new drugs approved by the FDA in 2022, eleven are small molecules containing at least one amide bond. Additionally, there are nineteen large molecules approved as new drugs, some of which have peptide structures, and therefore, also bear amide bonds. In recent years, multiple teams have embraced the challenge of developing more efficient methods for amide bond formation. This dedication has led to numerous publications appearing monthly in prestigious journals, showcasing significant advancements in this field. The primary goal of this review is to present the most viable strategies for constructing the amide bond. It is crucial to differentiate between amide bond formation and amide synthesis; hence, the focus is on describing specific methods for forming new C(O)−N bonds. In particular, this review concentrates on the methods developed within the last six years. There is a particular emphasis on new approaches that consider the thought process when selecting the starting materials and functional groups. This approach ensures coverage of all the most common chemical transformations that yield new amide bonds.

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One‐Step Biocatalytic Synthesis of Sustainable Surfactants by Selective Amide Bond Formation**

Cited by 7 publications

References 36 publications

Biocatalytic Carboxylate Reduction – Recent Advances and New Enzymes

Biocatalytic Carboxylate Reduction – Recent Advances and New Enzymes

Enzymatic Synthesis of Hydroxycinnamic Acid Amides in Water Using the Promiscuous Hydrolase/Acyltransferase PestE from Pyrobaculum calidifontis VA1

Contemporary Approaches for Amide Bond Formation

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