A Single Lipase‐Catalysed One‐Pot Protocol Combining Aminolysis Resolution and Aza‐Michael Addition: An Easy and Efficient Way to Synthesise β‐Amino Acid Esters

Xu, Fan; Wu, Qiongsi; Chen, Xiaoyang; Lin, Xianfu; Wu, Qi

doi:10.1002/ejoc.201500760

Cited by 18 publications

(8 citation statements)

References 45 publications

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“…The general interest in having mild and simple methodologies to introduce unfunctionalized C-N bonds via aza-Michael additions has resulted in multiple reports detailing new synthetic catalysts and strategies 43 , 44 . Consequently, a few enzymes have been discovered to catalyze an aza-Michael-type γ-addition that is similar to the addition half-reaction addressed here, although an entirely different, PLP-independent catalytic strategy is used to afford a new C-N bond 45 , 46 . Interestingly, an enzyme SbnA involved in the biosynthesis of l -2,3-diaminopropionic acid has recently been shown to catalyze a PLP-dependent β-replacement reaction utilizing the amine of l -Glu as a nucleophile for addition 47 .…”

Section: Discussionmentioning

confidence: 99%

Pyridoxal-5′-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis

et al. 2020

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Several nucleoside antibiotics are structurally characterized by a 5′′-amino-5′′-deoxyribose (ADR) appended via a glycosidic bond to a high-carbon sugar nucleoside, (5′ S ,6′ S )-5′- C -glycyluridine (GlyU). GlyU is further modified with an N -alkylamine linker, the biosynthetic origins of which have yet to be established. By using a combination of feeding experiments with isotopically labeled precursors and characterization of recombinant proteins from multiple pathways, the biosynthetic mechanism for N -alkylamine installation for ADR-GlyU-containing nucleoside antibiotics has been uncovered. The data reveal S -adenosyl- l -methionine (AdoMet) as the direct precursor of the N -alkylamine, but unlike conventional AdoMet- or decarboxylated AdoMet-dependent alkyltransferases, the reaction is catalyzed by a pyridoxal-5′-phophosate (PLP)-dependent aminobutyryltransferase (ABTase) using a stepwise γ-replacement mechanism that couples γ-elimination of AdoMet with aza-γ-addition onto the disaccharide alkyl acceptor. In addition to utilizing a conceptually different strategy for AdoMet-dependent alkylation, the newly discovered ABTases require a phosphorylated disaccharide alkyl acceptor, revealing a cryptic intermediate in the biosynthetic pathway.

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Section: Discussionmentioning

confidence: 99%

Pyridoxal-5′-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis

et al. 2020

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“…In this process, anhydrous http://ammonia is taken as a chiral derivatizing agent, and the reactions can be carried out efficiently in nonaqueous media at ambient temperatures. Additionally, it also finds application in the formation of beta‐amino acid esters, which are the primary constituents in a lot of pharmaceutical drugs [37], the production of pharmaceuticals like milnacipran that aids in the therapy of fibromyalgia syndrome [38], and the production of antimalarials [39] along with receptors of hormones [40]. Other application realms of lipase‐mediated aminolysis encompasses agrochemical and cosmetics items [41].…”

Section: The Structure and Catalytic Reactions Of Lipases: A Brief Overviewmentioning

confidence: 99%

Microbial lipase production: A deep insight into the recent advances of lipase production and purification techniques

Fatima

Faryad

Ataa

et al. 2020

Biotech and App Biochem

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Importance of enzymes is ever-rising particularly microbial lipases holding great industrial worth owing to their potential to catalyze a diverse array of chemical reactions in aqueous as well as nonaqueous settings. International lipase market is anticipated to cross USD 797.7 million till 2025, rising at a 6.2% compound annual growth rate from 2017 to 2025. The recent breakthrough in the field of lipase research is the generation of new and upgraded versions of lipases via molecular strategies. For example, integration of rational enzyme design and directed enzyme evolution to attain desired properties in lipases. Normally, purification of lipase with significant purity is achieved through a multistep procedure. Such multiple step approach of lipase purification entails both conventional and novel techniques. The present review attempts to provide an overview of different aspects of lipase production including fermentation techniques, factors affecting lipase production, and purification strategies, with the aim to assist researchers to pick a suitable technique for the production and purification of lipase.

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“…Some of the noteworthy pharmaceutical applications include peptide syntheses that contain usual and unusual amino acids produced by porcine pancreatic lipase and C. cylindracea lipase . Other examples are the synthesis of β‐amino acid esters, which are the chief components in many drugs, the synthesis of drugs such as milnacipran that help in clinical treatment of fibromyalgia, and the synthesis of potential anti‐malarial drugs as well as hormone receptors . The widespread usage of this reaction in the pharma domain is due to its potential in effective kinetic resolution of molecules .…”

Section: Lipase‐catalyzed Reactionsmentioning

confidence: 99%

Recent advances on sources and industrial applications of lipases

Sarmah

Revathi

Sheelu

et al. 2017

Biotechnology Progress

296

148

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Lipases are the industrially important biocatalysts, which are envisioned to have tremendous applications in the manufacture of a wide range of products. Their unique properties such as better stability, selectivity and substrate specificity position them as the most expansively used industrial enzymes. The research on production and applications of lipases is ever growing and there exists a need to have a latest review on the research findings of lipases. The present review aims at giving the latest and broadest overall picture of research and development on lipases by including the current studies and progressions not only in the diverse industrial application fields of lipases, but also with regard to its structure, classification and sources. Also, a special emphasis has been made on the aspects such as process optimization, modeling, and design that are very critical for further scale-up and industrial implementation. The detailed tabulations provided in each section, which are prepared by the exhaustive review of current literature covering the various aspects of lipase including its production and applications along with example case studies, will serve as the comprehensive source of current advancements in lipase research. This review will be very useful for the researchers from both industry as well as academia in promoting lipolysis as the most promising approaches to intensified, greener and sustainable processes. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 34:5-28, 2018.

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A Single Lipase‐Catalysed One‐Pot Protocol Combining Aminolysis Resolution and Aza‐Michael Addition: An Easy and Efficient Way to Synthesise β‐Amino Acid Esters

Cited by 18 publications

References 45 publications

Pyridoxal-5′-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis

Pyridoxal-5′-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis

Microbial lipase production: A deep insight into the recent advances of lipase production and purification techniques

Recent advances on sources and industrial applications of lipases

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