The sustainable synthesis of peptidomimetics <i>via</i> chemoenzymatic tandem oxidation–Ugi reaction

Madej, Arleta; Koszelewski, Dominik; Paprocki, Daniel; Brodzka, Anna; Ostaszewski, Ryszard

doi:10.1039/c8ra04583f

Cited by 10 publications

(9 citation statements)

References 49 publications

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“…Recently we have shown that enzymatic oxidation of alcohols to corresponding aldehydes catalysed by laccase from Trametes versicolor can be combine efficiently with the P-MCR. [32,38] Our investigations under the one-pot procedure was initiated by the laccase-catalysed aerobic oxidation of salicyl alcohol (6 a) which is the substrate for coumarin-3-carboxylic acid (1 a) (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

et al. 2020

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6‐O‐Glucose‐4‐phenylbutyrate was used successfully as promoting aqueous reaction medium for the synthesis of fourteen different α‐acyloxy carboxamides with the biologically relevant coumarin scaffold. Two different one‐pot protocols; chemical and chemoenzymatic, based on the usage of biodegradable surfactants for the synthesis of target products were developed. The chemoenzymatic method consists of 3‐steps in which the first step is oxidation catalyzed by Trametes versicolor laccase/O2, followed by spontaneous condensation reaction, and finally multicomponent Passerini reaction. All transformations occurred at room temperature in the same reaction vials without isolation of the reaction intermediates. The influence of the reaction conditions including substrate structure on the reaction course was studied. The application of an aqueous solution of 6‐O‐glucose 4‐phenylbutyrate as the reaction medium had the pivotal impact of the reaction rate providing target α‐acyloxy carboxamides with the yields up to 65 %. Obtained peptidomimetics were characterized by UV‐VIS and fluorescence spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

et al. 2020

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“…Particularly attractive is the opportunity to construct, via a MCR, (spiro)cyclic, constrained peptidomimetics, which are expected to possess improved absorption properties due to reduced number of rotatable chemical bonds and to better mimic characteristic structural biases in peptides and proteins, such as beta‐turns [161–163] . Recent steps towards efficient peptidomimetic synthesis were made by coupling biocatalysis to MCRs, through selective laccase‐oxidation of alcohol to a corresponding aldehyde and a following Ugi reaction [164] …”

Section: Discussionmentioning

confidence: 99%

“…[161][162][163] Recent steps towards efficient peptidomimetic synthesis were made by coupling biocatalysis to MCRs, through selective laccase-oxidation of alcohol to a corresponding aldehyde and a following Ugi reaction. [164] Of course, in this frame, the synergy with flow-based approaches represents an appealing horizon, still at its initial stages of exploration for peptidomimetic synthesis. The most significant examples in this context are reported in the next paragraph.…”

Section: Peptidomimetics: Relevance and Efforts Towards Sustainable P...mentioning

confidence: 99%

Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution

2022

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Formation of amide bonds is of immanent importance in organic and synthetic medicinal chemistry. Its presence in "traditional" small-molecule active pharmaceutical ingredients, in linear or cyclic oligo-and polypeptidic actives, including pseudopeptides, has led to the development of dedicated synthetic approaches for the formation of amide bonds starting from, if necessary, suitably protected amino acids. While the use of solid supported reagents is common in traditional peptide synthesis, similar approaches targeting amide bond formation in continuous-flow mode took off more significantly, after a first publication in 2006, only a couple of years ago. Most efforts rely upon the transition of traditional approaches in flow mode, or the combination of solid-phase peptide synthesis principles with flow chemistry, and advantages are mainly seen in improving space-time yields. This Review summarizes and compares the various approaches in terms of basic amide formation, peptide synthesis, and pseudopeptide generation, describing the technological approaches and the advantages that were generated by the specific flow approaches. A final discussion highlights potential future needs and perspectives in terms of greener and more sustainable syntheses.

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“…The sequential combination of U‐4CR and biocatalysis in a one‐pot fashion is still a relatively underexplored field. U‐4CR and biocatalysis have been successfully employed using lipase‐, laccase‐, or MAO‐N‐catalyzed processes for providing chiral building blocks in a stepwise fashion . Predominantly, enzyme catalysis is used for the kinetic racemate resolution or meso ‐desymmetrization of starting materials or products.…”

Section: Introductionmentioning

confidence: 99%

“…Predominantly, enzyme catalysis is used for the kinetic racemate resolution or meso ‐desymmetrization of starting materials or products. To date, only five protocols represent one‐pot concatenations of U‐4CR and enzyme catalysis,[9b], [9c], [9l], [9m], and only two examples are indeed one‐pot postmodifications. [9l], [9m] Additionally these two examples are the sole cases of lipase‐catalyzed post‐Ugi aminolysis.…”

Section: Introductionmentioning

confidence: 99%

Consecutive Five‐Component Ugi‐4CR‐CAL B‐Catalyzed Aminolysis Sequence and Concatenation with Transition Metal Catalysis in a One‐Pot Fashion to Substituted Triamides

Gesse

Müller

2019

Eur J Org Chem

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The concatenation of the Ugi four‐component synthesis and the CAL B‐catalyzed aminolysis of the intermediary formed Ugi methyl ester products furnishes a novel consecutive five‐component reaction for the formation of triamides. This one‐pot process is excellently compatible with metal catalyzed processes, such as copper‐catalyzed alkyne‐azide cycloaddition and Suzuki cross‐coupling or both in a one‐pot fashion. These novel consecutive six‐component syntheses represent a practical tool for synthesizing substrate libraries of complex triamide structures in a diversity‐oriented fashion.

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The sustainable synthesis of peptidomimetics via chemoenzymatic tandem oxidation–Ugi reaction

Abstract: A simply and green synthetic protocol based on the selective laccase-oxidation of alcohol to a corresponding aldehyde and a following Ugi reaction in a micellar system made of SDS was developed and is reported herein.

Cited by 10 publications

References 49 publications

Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution

Consecutive Five‐Component Ugi‐4CR‐CAL B‐Catalyzed Aminolysis Sequence and Concatenation with Transition Metal Catalysis in a One‐Pot Fashion to Substituted Triamides

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