Hydrolysis and Formation of Hydantoins

Ogawa, Jun; Horinouchi, Nobuyuki; Shimizu, Sakayu

doi:10.1002/9783527639861.ch16

Cited by 7 publications

(5 citation statements)

References 128 publications

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“…The enzymatic hydrolysis of hydantoin is mostly performed using D-hydantoinase and D-N-carbamoylase (Scheme 2, pathway B). 35 D-Hydantoinase first selectively cleaves Dhydantoins to afford N-carbamoyl-D-amino acids (21) which, in the presence of D-N-carbamoylase, is converted into free Damino acids (20). D-p-hydroxyphenyl glycine is the valuable precursor for penicillins and cephalosporins which is commercially obtained by this technique.…”

Section: Synlett Accountmentioning

confidence: 99%

“…Many of the compounds exhibit strong bioactivity and thus have been led through clinical trials to the commercialized drugs. Some of these potent drugs include phenytoin (29), fosphenytoin (30), and ethotoin (31), as anticonvulsants; nitrofurantoin (33) and dantrium (34) as muscle relaxants; and nilutamide (32) and enzalutamide (35) as androgen receptor antagonists (Figure 5). Recently, the medicinal applications of hydantoin and thiohydantoin have been exhaustively reviewed by Shin, 7 hence we will briefly introduce biological property.…”

Section: Biological Propertiesmentioning

confidence: 99%

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Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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Section: Synlett Accountmentioning

confidence: 99%

Section: Biological Propertiesmentioning

confidence: 99%

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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“…On the contrary to chemical methods, the enzymatic hydrolysis of hydantoins enables the corresponding amino acid to be obtained enantioselectivelys. d -Hydantoinase is the most common enzyme to produce d -amino acids from racemic hydantoins, l -hydantoinase is more rarely found in Nature and moreover needs ATP as well as Mn 2+ , Mg 2+ , or K + as cofactors to be selectively active toward l -substrates …”

Section: Preparation Of Amino Acids From Hydantoinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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“…The "hydantoinase process" is one of the most widely-used enzymatic methods for the production of optically pure ␣-amino acids [12][13][14]. In this cascade process, the chemically synthesized d,l-5-monosubstituted hydantoin ring is first hydrolyzed by an enantioselective hydantoinase.…”

Section: Introductionmentioning

confidence: 99%

Rational re-design of the “double-racemase hydantoinase process” for optically pure production of natural and non-natural l-amino acids

Rodríguez-Alonso

Clemente-Jiménez

Rodríguez‐Vico

et al. 2015

Biochemical Engineering Journal

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Hydrolysis and Formation of Hydantoins

Cited by 7 publications

References 128 publications

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

Rational re-design of the “double-racemase hydantoinase process” for optically pure production of natural and non-natural l-amino acids

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