Enzyme-Catalyzed Direct Three-Component Aza-Diels–Alder Reaction Using Hen Egg White Lysozyme

He, Yan‐Hong; Hu, Wen; Guan, Zhi

doi:10.1021/jo2016696

Cited by 41 publications

(21 citation statements)

References 23 publications

(14 reference statements)

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“…The transformation has broad scope and tolerates different amines and aldehydes. [78] The stereoselectivity of the reaction can be modulated by variation of temperature and solvent. For instance, complete diastereoselectivity in favor of the exo-product 140 was observed if the reaction was carried out at 25 8C in pure water.…”

Section: Methodsmentioning

confidence: 99%

The Asymmetric Hetero‐Diels–Alder Reaction in the Syntheses of Biologically Relevant Compounds

Eschenbrenner‐Lux¹,

Kumar²,

Waldmann³

2014

Angew Chem Int Ed

206

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The hetero-Diels-Alder reaction is one of the most powerful transformations in the chemistry toolbox for the synthesis of aza- and oxa-heterocycles embodying multiple stereogenic centers. However, as compared to other cycloadditions, in particular the dipolar cycloadditions and the Diels-Alder reaction, the hetero-Diels-Alder reaction has been much less explored and exploited in organic synthesis. Nevertheless, this powerful transformation has opened up efficient and creative routes to biologically relevant small molecules and different natural products which contain six-membered oxygen or nitrogen ring systems. Recent developments in this field, in particular in the establishment of enantioselectively catalyzed hetero-Diels-Alder cycloadditions steered by a plethora of different catalysts and the application of the resulting small molecules in chemical biology and medicinal chemistry research, are highlighted in this Minireview.

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Section: Methodsmentioning

confidence: 99%

The Asymmetric Hetero‐Diels–Alder Reaction in the Syntheses of Biologically Relevant Compounds

Eschenbrenner‐Lux¹,

Kumar²,

Waldmann³

2014

Angew Chem Int Ed

206

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“…For instance, the direct three‐component aza‐Diels–Alder reaction between an aromatic aldehyde (1 equiv), aromatic amine (3 equiv) and 2‐cyclohexen‐1‐one (3 equiv) was catalyzed by hen egg‐white lysozyme (HEWL), a hydrolase from the glycosylase family. The azabicycles were obtained in 69–97% isolated yields and an endo / exo selectivity up to 90:10 after several days in a mixture of MeCN/water (9:1) at 35°C (Scheme ) . Furthermore, 4‐thiazolidinones have been efficiently obtained in a one‐pot reaction between an amine, an aldehyde, and mercaptoacetic acid used in equimolar amounts, catalyzed by trypsin from porcine pancreas (42–89% isolated yield, Scheme ) .…”

Section: Hydrolases In Multicomponent and Tandem Nonconventional Reacmentioning

confidence: 99%

Recent Advances in Biocatalytic Promiscuity: Hydrolase‐Catalyzed Reactions for Nonconventional Transformations

López-Iglesias

Gotor‐Fernández

2015

The Chemical Record

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Enzymes has emerged in recent decades as ideal catalysts for synthetic transformations in mild reaction conditions. Their capacity to accelerate a myriad of biotransformations with high levels of selectivity and broad substrate specificity including excellent atom economy has led to a current full recognition. The six classes of enzymes (oxidoreductases, transferases, hydrolases, lyases, isomerases and ligases) possess outstanding abilities to perform specific modifications in target molecules. Nevertheless, in the last fifteen years, novel examples have appeared related to nonconventional processes catalyzed by various classes of biocatalysts. Amongst these, hydrolases have received special attention since they display remarkable activities in initially unexpected reactions such as carbon-carbon and carbon-heteroatom bond formation reactions, oxidative processes and novel hydrolytic transformations. In this review, the main findings in this area will be disclosed, highlighting the catalytic properties of hydrolases not only to catalyze single processes but also multicomponent and tandem nonconventional reactions.

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“…He et al [74] reported for the first time that hen egg white lysozyme (HEWL) efficiently promotes the onepot, three-component aza-Diels-Alder reaction of aromatic aldehydes, aromatic amine and 2-cyclohexen-1-one. Under optimised conditions, yields up to 98% and stereoselectivity of endo/exo ratios up to 90:10 were obtained.…”

Section: Catalytic Promiscuity: Beyond Lipasesmentioning

confidence: 99%

Enzyme promiscuity: using the dark side of enzyme specificity in white biotechnology

Arora

Mukherjee

Gupta

2014

Sustain Chem Process

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Enzyme promiscuity can be classified into substrate promiscuity, condition promiscuity and catalytic promiscuity. Enzyme promiscuity results in far larger ranges of organic compounds which can be obtained by biocatalysis. While early examples mostly involved use of lipases, more recent literature shows that catalytic promiscuity occurs more widely and many other classes of enzymes can be used to obtain diverse kinds of molecules. This is of immense relevance in the context of white biotechnology as enzyme catalysed reactions use greener conditions.

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Enzyme-Catalyzed Direct Three-Component Aza-Diels–Alder Reaction Using Hen Egg White Lysozyme

Cited by 41 publications

References 23 publications

The Asymmetric Hetero‐Diels–Alder Reaction in the Syntheses of Biologically Relevant Compounds

The Asymmetric Hetero‐Diels–Alder Reaction in the Syntheses of Biologically Relevant Compounds

Recent Advances in Biocatalytic Promiscuity: Hydrolase‐Catalyzed Reactions for Nonconventional Transformations

Enzyme promiscuity: using the dark side of enzyme specificity in white biotechnology

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