Stereoselective nitrile hydratase

Shen, Yingqiang; Du, Fangchuan; Gao, Weifang; Wang, Anming; Chen, Chanyu

doi:10.5897/ajmr12.101

Cited by 4 publications

(6 citation statements)

References 41 publications

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“…This is not unexpected at a ferric center, since Fe(III) is also found at the active site of nitrile hydratase. 4,5,7,8 In the present case, the hydration reaction is performed by a ferrous Fe(II) center, which is unusual.…”

Section: ■ Discussionmentioning

confidence: 77%

“…Nature is able to perform such reactions: the nitrile hydratases constitute a class of enzymes with iron- or cobalt-containing active sites. ,− The promising reactivity of these biomolecules gives rise to a number of studies carried out from the biological material. However, the difficulties inherent to the extensive use of the biological media for synthesis are still inciting chemists to study more classical synthetic pathways.…”

Section: Introductionmentioning

confidence: 99%

“…The reaction conditions however are not always in line with the current demand in terms of eco-compatibility. In any case, it seems obvious that the nitrile has to be activated either by coordination or by interaction with its own environment, according to three different possible pathways involving (i) an inner-sphere mechanism, (ii) an outer-sphere mechanism, or (iii) a second-outer sphere mechanism. ,− From a general and fundamental point of view the question of nitrile hydration by first-row and cheap metal centers in mild conditions is of particular interest and justifies further studies.…”

Section: Introductionmentioning

confidence: 99%

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Steric Congestion at, and Proximity to, a Ferrous Center Leads to Hydration of α-Nitrile Substituents Forming Coordinated Carboxamides

et al. 2014

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The question of the conversion of nitrile groups into amides (nitrile hydration) by action of water in mild and eco-compatible conditions and in the presence of iron is addressed in this article. We come back to the only known example of hydration of a nitrile function into carboxamide by a ferrous [Fe(II)] center in particularly mild conditions and very efficiently and demonstrate that these unusual conditions result from the occurrence of steric stress at the reaction site and formation of a more stable end product. Two bis(cyano-substituted) (tris 2-pyridyl methyl amine) ligands have been prepared, and the structures of the corresponding FeCl2 complexes are reported, both in the solid state and in solution. These two ligands only differ by the position of the nitrile group on the tripod in the α and β position, respectively, with respect to the pyridine nitrogen. In any case, intramolecular coordination is impossible. Upon action of water, the nitrile groups are hydrated however only if they are located in the α position. The fact that the β-substituted β-(NC)2TPAFeCl2 complex is not water sensitive suggests that the reaction proceeds in an intramolecular way at the vicinity of the metal center. In the bis α-substituted α-(NC)2TPAFeCl2 complex, both functions are converted in a very clean fashion, pointing out that this complex exhibits ligand flexibility and is not deactivated after the first hydration. At a preparative scale, this reaction allows the one-pot conversion of the bis(cyano-substituted) tripod into a bis(amido-substituted) one in particularly mild conditions with a very good yield. Additionally, the XRD structure of a ferric compound in which the two carboxamido ligands are bound to the metal in a seven-coordinate environment is reported.

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Section: ■ Discussionmentioning

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Steric Congestion at, and Proximity to, a Ferrous Center Leads to Hydration of α-Nitrile Substituents Forming Coordinated Carboxamides

et al. 2014

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“…During the past few years, studies focusing on stereoselective NHase have advanced tremendously (Table 2). Several stereoselective NHases from the genera of Agrobacterium, Moraxella, Serratia, Rhodococcus, and Pseudomonas have been isolated (Shen et al, 2012a). Pawar and Yadav (2014) cross linked NHase from R. rhodochrous ATCC BAA-870 with poly (vinyl alcohol) (PVA)/chitosan-glutaraldehyde and the immobilized NHase showed 81% enantiomeric excess (ee p ) toward R-mandelonitrile.…”

Section: Stereoselectivitymentioning

confidence: 99%

“…Over the past few years, rapid progress with respect to NHase has been made and valuable information has been summarized. Quite a few reviews on the applications of NHase in biocatalysis have been published (Prasad and Bhalla, 2010), most of these focusing on either the industrialization of NHase or its structure and expression (Shen et al, 2012c;Mascharak, 2014;Gong et al, 2017;Supreetha et al, 2019;Jiao et al, 2020). In this review, we summarize newly available information regarding the natural distribution and types, posttranslational maturation, catalytic mechanisms, biochemical properties, and applications of NHase.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications

Cheng

Xia

Zhou

2020

Front. Bioeng. Biotechnol.

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Nitrile hydratase (NHase, EC 4.2.1.84) is one type of metalloenzyme participating in the biotransformation of nitriles into amides. Given its catalytic specificity in amide production and eco-friendliness, NHase has overwhelmed its chemical counterpart during the past few decades. However, unclear catalytic mechanism, low thermostablity, and narrow substrate specificity limit the further application of NHase. During the past few years, numerous studies on the theoretical and industrial aspects of NHase have advanced the development of this green catalyst. This review critically focuses on NHase research from recent years, including the natural distribution, gene types, posttranslational modifications, expression, proposed catalytic mechanism, biochemical properties, and potential applications of NHase. The developments of NHase described here are not only useful for further application of NHase, but also beneficial for the development of the fields of biocatalysis and biotransformation.

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