Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

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

doi:10.1016/j.molcatb.2011.12.005

Cited by 29 publications

(24 citation statements)

References 40 publications

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“…Prior to running the reactions, we confirmed our earlier observation (Chhiba et al . ) that 3‐amino‐3‐phenylpropionitrile was only hydrolysed at pH 9 where the amine tends to be in the uncharged state, rather than the protonated form which dominates at lower pH (Fig. ) and thereby defined the higher‐than‐usual reaction medium pH for that substrate.…”

Section: Resultsmentioning

confidence: 99%

“…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%

“…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 . ), and hence this compound could not be used in a growth‐based primary screen to discover new biocatalysts. Moreover, the possible release of the amino group at the beta position through alternative enzyme reactions would have made the nitrogen dependent screen results ambiguous.…”

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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Section: Resultsmentioning

confidence: 99%

“…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%

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Hydrolysis of nitriles by soil bacteria: variation with soil origin

et al. 2017

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“…2 Representatives of this class are wellknown not only as versatile intermediates in organic synthesis and in many other reactions, 3,4 but also as reagents for synthesis of heterocyclic compounds, 5 inhibitors of enzymes, 6 precursors of peptides, 7 amino-acids, 8 which, in turn, exhibit antibiotic, 9 antifungal, 10 and other important biological and pharmacological properties. 11,12 The coordination behaviour of aminonitriles in the complexation reactions with Cu(I) salts can be characterized on the basis of only several related, 13,14 or closely related, 15 compounds, though the matter under discussion is still relevant.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of [Cu(Hapn)]NO3]NO3, [Cu(Hapn)(H2O)2]SiF6, [Cu(Hapn)(H2O)BF4]BF4∙H2O and [Cu(Hapn)(NH2SO3)2] π-complexes (apn = 3-(prop-2-en-1-ylamino)propanenitrile)

Luk'yanov

Goreshnik

Kinzhybalo

et al. 2017

ACSi

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. Obtained compounds were characterized by single-crystal X-ray diffraction and partially by IR spectroscopy. In the structures of complexes 1, 2 and 4 Cu(I) cation possesses a tetrahedral environment formed by the C=C bond of one organic cation Hapn, the N atom of cyano group from another Hapn moiety, and two O atoms (from NO 3 -anions in 1, from H 2 O molecules in 2) or N atoms (NH 2 SO 3 -anions in 4). In compound 3 strongly pronounced trigonal-pyramidal coordination environment of Cu(I) is formed by a mid-point of C=C-bond of one Hapn cation, nitrogen atom (of cyano group) of another Hapn unit, O atom of H 2 O molecule in the basal plane, and F atom of BF 4 -anion at the apical position.

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“…In another recent example, R. rhodochrous ATCC BAA-870 was used for the biocatalytic hydrolysis of β-aminonitriles to β-amino-amides [14]. One example for a rather rarely investigated reaction would be the biocatalytic hydration of 3-methyl- or 3-ethyl-2-butenolide from the corresponding ( R )-3-hydroxy-3-alkylbutanolide, a phenomenon observed in resting cells of Rhodococcus rhodochrous strain ATCC 17895 [15].…”

Section: Introductionmentioning

confidence: 99%

Draft genome sequence of Rhodococcus rhodochrous strain ATCC 17895

Chen¹,

Otten²,

Resch³

et al. 2013

Stand. Genomic Sci.

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Rhodococcus rhodochrous ATCC 17895 possesses an array of mono- and dioxygenases, as well as hydratases, which makes it an interesting organism for biocatalysis. R. rhodochrous is a Gram-positive aerobic bacterium with a rod-like morphology. Here we describe the features of this organism, together with the complete genome sequence and annotation. The 6,869,887 bp long genome contains 6,609 protein-coding genes and 53 RNA genes. Based on small subunit rRNA analysis, the strain is more likely to be a strain of Rhodococcus erythropolis rather than Rhodococcus rhodochrous.

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Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

Cited by 29 publications

References 40 publications

Hydrolysis of nitriles by soil bacteria: variation with soil origin

Hydrolysis of nitriles by soil bacteria: variation with soil origin

Synthesis and Structure of [Cu(Hapn)]NO3]NO3, [Cu(Hapn)(H2O)2]SiF6, [Cu(Hapn)(H2O)BF4]BF4∙H2O and [Cu(Hapn)(NH2SO3)2] π-complexes (apn = 3-(prop-2-en-1-ylamino)propanenitrile)

Draft genome sequence of Rhodococcus rhodochrous strain ATCC 17895

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