Heterocycles 38. Biocatalytic Synthesis of New Heterocyclic Mannich Bases and Derivatives

Leonte, Denisa; Bencze, László Csaba; Paizs, Csaba; Irimie, Florin Dan; Zaharia, Valentin

doi:10.3390/molecules200712300

Cited by 11 publications

(10 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The catalytic activity of lipase from Candida antarctica lipase B (CAL-B) in Mannich reactions was studied by the group of Zaharia, who showed that this enzyme was very effective in the synthesis of new Mannich bases derived from 2-phenylthiazole and 2-phenylaminothiazole ( Scheme 15 ). While the reaction worked well with acetone as the nucleophile component, affording the target compounds with good yields in mild and ecofriendly reaction conditions, this enzyme proved inactive with other ketones [ 76 , 77 ].…”

Section: The Mannich Reactionmentioning

confidence: 99%

Bio-Catalysis in Multicomponent Reactions

Jumbam

Masamba

2020

Molecules

View full text Add to dashboard Cite

Enzyme catalysis is a very active research area in organic chemistry, because biocatalysts are compatible with and can be adjusted to many reaction conditions, as well as substrates. Their integration in multicomponent reactions (MCRs) allows for simple protocols to be implemented in the diversity-oriented synthesis of complex molecules in chemo-, regio-, stereoselective or even specific modes without the need for the protection/deprotection of functional groups. The application of bio-catalysis in MCRs is therefore a welcome and logical development and is emerging as a unique tool in drug development and discovery, as well as in combinatorial chemistry and related areas of research.

show abstract

Section: The Mannich Reactionmentioning

confidence: 99%

Bio-Catalysis in Multicomponent Reactions

Jumbam

Masamba

2020

Molecules

View full text Add to dashboard Cite

show abstract

“…Leonte et al [58] described the biocatalytic synthesis of new Mannich bases containing various heterocyclic rings (thiazole, furane, thiophene, pyridine) by applying the lipase catalyzed trimolecular condensation of the corresponding heterocyclic aldehydes (50) with acetone (52) and primary aromatic amines (51) in mild and eco-friendly reaction conditions (Scheme-XV). Penicillin acylase isolated from E. coli hydrolyzes the different forms of penicillin such as penicillin G (58) into 6-aminopenicillinic acid (6-APA) (…”

Section: Scheme-v: Epoxidation Using Cytochrome P450 Enzymementioning

confidence: 99%

Role of Enzymes in Synthesis of Biologically Important Organic Scaffolds

Gupta

Chundawat

2019

Asian J. Chem.

View full text Add to dashboard Cite

Green route of biogenic synthesis of heterocyclic compounds via microbes (bacteria, fungi, virus, yeast, algae, etc.) has the potential to deliver clean manufacturing technology. The application of biocatalysts for the synthesis of novel compounds has attracted increasing attention over the past few years and consequently, high demands have been placed on the identification of new biocatalysts for organic synthesis. Enzymes play an increasingly important role as biocatalysts in the synthesis of key intermediates for the pharmaceutical and chemical industry, and new enzymatic technologies. The characteristics of biocatalyst can be tailored with protein engineering and metabolic engineering methods to meet the desired process conditions. This review discusses the synthetic application of all the six classes of enzymes which are oxidoreductase, transferase, hydrolase, lyase, isomerase and ligase. Enzymes are highly selective catalysts and their contribution to regio-, chemo- and stereoselectivity of compounds were also discussed.

show abstract

“…8−16 Amidation of aniline and formation of a Mannich base was carried out using lipase as a catalyst. 13,14 To explore the complete potential, the promiscuous nature of lipase can be explored by varying the source of lipase-producing bacteria or fungi. 1−3 This makes lipase a suitable catalyst for the synthesis of a range of chemicals.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Acetylation of 2-Aminophenol Using Immobilized Lipase: Process Optimization, Mechanism, and Kinetics

Magadum

Yadav

2018

ACS Omega

View full text Add to dashboard Cite

acetamide is an intermediate for the complete natural synthesis of antimalarial drugs. Chemoselective monoacetylation of the amino group of 2-aminophenol to N-(2-hydroxyphenyl)acetamide was carried out by employing Novozym 435 as the catalyst. Different acyl donors such as vinyl acetate, vinyl butyrate, acetic anhydride, and ethyl acetate were studied. The effect of various parameters such as different acyl donors, speed of agitation, solvent, catalyst loading, mole ratio, and temperature was studied. Vinyl acetate was found to be the best acyl donor among the studied acyl donors since it leads to an irreversible reaction. It is a kinetically controlled synthesis since vinyl acetate was used as the activated acyl donor. The substrate to acyl donor ratio was 1:3. The mechanism for the given reaction system was predicted based on the observations of Lineweaver− Burk plots. It was observed that the reaction followed a ternary complex model with inhibition by vinyl acetate, and kinetic constants were estimated using the Polymath 6.0 software. Under the final optimized conditions, the conversion for the reaction was found to be 74.6% in 10 h.

show abstract

Heterocycles 38. Biocatalytic Synthesis of New Heterocyclic Mannich Bases and Derivatives

Cited by 11 publications

References 14 publications

Bio-Catalysis in Multicomponent Reactions

Bio-Catalysis in Multicomponent Reactions

Role of Enzymes in Synthesis of Biologically Important Organic Scaffolds

Chemoselective Acetylation of 2-Aminophenol Using Immobilized Lipase: Process Optimization, Mechanism, and Kinetics

Contact Info

Product

Resources

About