Biocatalyst Process: Enzymatic Transformation of Nitrile Compounds and The Application

Ryuno, Koichiro; Nakamura, T.

doi:10.5059/yukigoseikyokaishi.61.517

Cited by 6 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In nature the nitrile hydratase enzyme (NHase), a metallo-enzyme that usually presents Fe 3+ and Co 3+ in its active site, , efficiently and selectively catalyzes the hydration of organic nitriles to amides and, for this reason, bacteria containing those proteins have been widely adopted at the industrial level since 1980, also in the production of pharmaceutical compounds. ,, In the presence of this microorganism the reaction proceeds at room temperature and under physiological pH conditions. , On the other hand, the NHase enzyme showed poor thermostability, which limits a more efficient and sustainable application, since the amide production is an exergonic process that requires continuous temperature control with a high energy demand . In addition, the NHase showed substrate affinity that further limits a wider application. , …”

Section: Introductionmentioning

confidence: 99%

“…3,10,11 In the presence of this microorganism the reaction proceeds at room temperature and under physio-logical pH conditions. 12,13 On the other hand, the NHase enzyme showed poor thermostability, which limits a more efficient and sustainable application, since the amide production is an exergonic process that requires continuous temperature control with a high energy demand. 14 In addition, the NHase showed substrate affinity that further limits a wider application.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Hydration of Aromatic Nitriles Catalyzed by Mn-OH Complexes: A Rationalization from Quantum Chemical Investigations

et al. 2020

View full text Add to dashboard Cite

The nitrile hydration reaction mechanism catalyzed by a Mn I (NH)-OH complex has been elucidated by means of DFT computations, first exploring three mechanistic hypotheses experimentally suggested in the literature and then proposing a novel catalytic cycle proceeding along a combination of two pathways, suitable to describe the whole process. The results show that the reaction proceeds through a nucleophilic attack by the hydroxide to the Mn-coordinated nitrile substrate, leading to amide formation, ultimately released as the iminol tautomer upon a Mn−N to Mn−O switching step. A rapid tautomerization to yield the amide product closes the cycle. An explanation of the enhancement of the experimental turnover number (TON) with the electron-withdrawing properties of the substituents was also provided by comparing the free energy profiles obtained for the hydration of benzonitrile (PhCN), p-N-dimethylbenzonitrile (NMe 2 PhCN) and p-trifluoromethylbenzonitrile (CF 3 PhCN) substrates, which nicely combines experimental and theoretical results. In addition, to introduce a further advance in this novel field and to gain useful insights for the design of more efficient Mn I catalysts, a newly designed Mn(NCH 3 )-OH complex is investigated herein and proposed for the nitrile hydration reaction, interestingly showing an improved catalytic activity in comparison with the previous Mn I (NH)-OH complex.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Hydration of Aromatic Nitriles Catalyzed by Mn-OH Complexes: A Rationalization from Quantum Chemical Investigations

et al. 2020

View full text Add to dashboard Cite

show abstract

“…For instance, the NHases from P. chlororaphis B23 and Rhodococcus sp. N-774 become unstable above 20 • C (Hann et al, 1999;Ryuno and Nakamura, 2003), and the NHase from R. rhodochrous J1 is merely stable between 10 and 30 • C (Wieser et al, 1998). Since the hydration of nitrile is an exothermic reaction, NHases must be stabilized by keeping the temperature at a low level, but this might result in an uncontrollable increase in energy cost.…”

Section: Stability Of Nhasementioning

confidence: 99%

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

Cheng

Xia

Zhou

2020

Front. Bioeng. Biotechnol.

View full text Add to dashboard Cite

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.

show abstract

Nitrilase and Its Application as a ‘Green’ Catalyst

Savan

Sharma

Tewari

et al. 2006

C&B

View full text Add to dashboard Cite

Hydrolase-catalyzed reactions have been widely applied in organic synthesis. Nitrilases are an important class of hydrolase that converts naturally occurring, as well as xenobiotically derived, nitriles to the corresponding carboxylic acids and ammonia. Because of their inherent enantio- and regioselectivities and other benefits, nitrilases are attractive as 'green', mild, and selective catalysts for setting stereogenic centers in fine-chemical synthesis and enantiospecific synthesis of a variety of carboxylic acid derivatives. In this review, the literature has been surveyed to provide a comprehensive coverage of the application of nitrilases in organic synthesis. Literature has also been cited to describe the isolation and/or characterization of nitrilases and related enzymes.

show abstract

Biocatalyst Process: Enzymatic Transformation of Nitrile Compounds and The Application

Cited by 6 publications

References 0 publications

Hydration of Aromatic Nitriles Catalyzed by Mn-OH Complexes: A Rationalization from Quantum Chemical Investigations

Hydration of Aromatic Nitriles Catalyzed by Mn-OH Complexes: A Rationalization from Quantum Chemical Investigations

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

Nitrilase and Its Application as a ‘Green’ Catalyst

Contact Info

Product

Resources

About