Enzymatic Stereoselective Synthesis of β‐Amino Acids

Chhiba, Varsha; Bode, Moira L.; Mathiba, Kgama; Brady, Dean

doi:10.1002/9783527682492.ch14

Cited by 8 publications

(6 citation statements)

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“…It is of interest to synthetic organic chemists to have access to suitable biocatalysts to synthesise β ‐substituted amides and acids (Chhiba et al . , ; Rudat et al . ; Coady et al .…”

Section: Discussionmentioning

confidence: 99%

“…It is of interest to synthetic organic chemists to have access to suitable biocatalysts to synthesise b-substituted amides and acids (Chhiba et al 2012(Chhiba et al , 2014Rudat et al 2012;Coady et al 2013), which can be used as precursors for the synthesis of peptidomimetics and other pharmaceuticals. However, in our search the chiral compound 3-amino-3-phenylpropionitrile 8 was only hydrolysed at pH 9 or above by a strain of R. rhodochrous (Chhiba et al 2012), and hence this compound could not be used in a growth-based primary screen to discover new biocatalysts.…”

Section: Discussionmentioning

confidence: 99%

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Hydrolysis of nitriles by soil bacteria: variation with soil origin

et al. 2017

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Enzymes are typically substrate specific in their catalytic reactions, and this means that a wide diversity of enzymes is required to provide a comprehensive biocatalysis toolbox. This paper shows that the microbial diversity of nitrile hydrolysis activity can be targeted according to land utilization. Nitrile biocatalysis is a green chemical method for the enzymatic production of amides and carboxylic acids that has industrial applications, such as in the synthesis of acrylamide and nicotinamide. The biocatalysts discovered in this study may be applied to the synthesis of peptidomimetics which are an important class of therapeutic compounds.

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“…It is of interest to synthetic organic chemists to have access to suitable biocatalysts to synthesise β ‐substituted amides and acids (Chhiba et al . , ; Rudat et al . ; Coady et al .…”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Hydrolysis of nitriles by soil bacteria: variation with soil origin

et al. 2017

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“…Interestingly, the nitrile hydratase-amidase system can enantioselectively hydrolyse some compounds, while the nitrilase hydrolyses the opposite enantiomer of similar nitriles [37]. Biocatalytic nitrile hydrolysis affords valuable applications in industry, including production of solvents, extractants, pharmaceuticals, drug intermediates, and pesticides [38–41]. Herein, we describe the sequencing and annotation of R. rhodochrous ATCC BAA-870, identifying the genes associated with nitrile hydrolysis as well as other genes for potential biocatalytic applications.…”

Section: Introductionmentioning

confidence: 99%

The complete genome sequence of the nitrile biocatalyst Rhodococcus rhodochrous ATCC BAA-870

Frederick

Hennessy

Horn³

et al. 2020

BMC Genomics

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BackgroundRhodococci are industrially important soil-dwelling Gram-positive bacteria that are well known for both nitrile hydrolysis and oxidative metabolism of aromatics. Rhodococcus rhodochrous ATCC BAA-870 is capable of metabolising a wide range of aliphatic and aromatic nitriles and amides. The genome of the organism was sequenced and analysed in order to better understand this whole cell biocatalyst.ResultsThe genome of R. rhodochrous ATCC BAA-870 is the first Rhodococcus genome fully sequenced using Nanopore sequencing. The circular genome contains 5.9 megabase pairs (Mbp) and includes a 0.53 Mbp linear plasmid, that together encode 7548 predicted protein sequences according to BASys annotation, and 5535 predicted protein sequences according to RAST annotation. The genome contains numerous oxidoreductases, 15 identified antibiotic and secondary metabolite gene clusters, several terpene and nonribosomal peptide synthetase clusters, as well as 6 putative clusters of unknown type. The 0.53 Mbp plasmid encodes 677 predicted genes and contains the nitrile converting gene cluster, including a nitrilase, a low molecular weight nitrile hydratase, and an enantioselective amidase.Although there are fewer biotechnologically relevant enzymes compared to those found in rhodococci with larger genomes, such as the well-known Rhodococcus jostii RHA1, the abundance of transporters in combination with the myriad of enzymes found in strain BAA-870 might make it more suitable for use in industrially relevant processes than other rhodococci.ConclusionsThe sequence and comprehensive description of the R. rhodochrous ATCC BAA-870 genome will facilitate the additional exploitation of rhodococci for biotechnological applications, as well as enable further characterisation of this model organism. The genome encodes a wide range of enzymes, many with unknown substrate specificities supporting potential applications in biotechnology, including nitrilases, nitrile hydratase, monooxygenases, cytochrome P450s, reductases, proteases, lipases, and transaminases.

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“…Compounds such as 3-hydroxy-4-aryloxybutanenitriles, 3benzoyloxypentanedinitriles and 3-amino-3-p-tolylpropanenitrile were enantioselectively hydrolysed by the nitrile hydratase-amidase system, while the nitrilase hydrolysed the opposite enantiomer of 3amino-3-phenylpropanenitrile [36]. Biocatalytic nitrile hydrolysis affords valuable applications in industry, including production of solvents, extractants, pharmaceuticals, drug intermediates, and pesticides [37][38][39][40]. Herein, we describe the sequencing and annotation of R. rhodochrous ATCC BAA-870, identifying the genes associated with nitrile hydrolysis as well as other genes for potential biocatalytic applications.…”

Section: Introductionmentioning

confidence: 99%

The biotechnological relevance of Rhodococcus rhodochrous. The complete genomic sequence of nitrile biocatalyst strain ATCC BAA-870.

Frederick

Hennessy

Horn

et al. 2019

Preprint

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Background Rhodococci are industrially important soil-dwelling Gram-positive bacteria that are well known for both nitrile hydrolysis and oxidative metabolism of aromatics. Rhodococcus rhodochrous ATCC BAA-870 is capable of metabolising a wide range of aliphatic and aromatic nitriles and amides. The expressed nitrilase, nitrile hydratase and amidase activities have shown stereoselective preferences for beta-substituted nitrile compounds. The genome of the organism was sequenced and analysed in order to better understand this whole cell biocatalyst. Results The genome of R. rhodochrous ATCC BAA-870 is the first Rhodococcus genome fully sequenced using Nanopore sequencing. The circular genome contains 5.9 megabase pairs (Mbp) and includes a 0.53 Mbp linear plasmid, that together encode 7548 predicted protein sequences according to BASys annotation, and 5535 predicted protein sequences according to RAST annotation. The genome contains numerous oxidoreductases, 15 identified antibiotic and secondary metabolite gene clusters, and several terpene and nonribosomal peptide synthetase clusters, as well as 6 putative clusters of unknown type. The 0.53 Mbp plasmid encodes 677 predicted genes and contains the nitrile converting gene cluster. Based on COG functional categories of proteins using RAST annotation, the main distributions of predicted annotated genes belong to known subsystems encoding amino acids and derivatives (19.7%), carbohydrates (13.4%), fatty acids, lipids and isoprenoids (12.2%), and cofactors, vitamins, prosthetic groups and pigments (9.4%). However, 74% of RAST annotated genes are not assigned clear functional roles within known metabolic pathways, and 38% of genes are annotated as hypothetical. BASys annotation predicts that 55% of annotated genes have an unknown function. The R. rhodochrous ATCC BAA-870 genome contains one possible CRISPR, identified by CRISPRCasFinder. Conclusions The sequence and comprehensive description of the R. rhodochrous ATCC BAA-870 genome will facilitate the additional exploitation of rhodococci for biotechnological applications, as well as enable further characterisation of this model organism. The genome encodes a wide range of enzymes, many with unknown substrate specificities supporting potential applications in biotechnology, including monooxygenases, cytochrome P450s, reductases, proteases, lipases, and transaminases. The capacity of this strain to hydrolyse nitriles resides upon a plasmid, containing a nitrilase, a low molecular weight nitrile hydratase, and an enantioselective amidase.

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Enzymatic Stereoselective Synthesis of β‐Amino Acids

Cited by 8 publications

References 64 publications

Hydrolysis of nitriles by soil bacteria: variation with soil origin

Hydrolysis of nitriles by soil bacteria: variation with soil origin

The complete genome sequence of the nitrile biocatalyst Rhodococcus rhodochrous ATCC BAA-870

The biotechnological relevance of Rhodococcus rhodochrous. The complete genomic sequence of nitrile biocatalyst strain ATCC BAA-870.

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