Biocatalytic promiscuity: lipase-catalyzed asymmetric aldol reaction of heterocyclic ketones with aldehydes

Guan, Zhi; Fu, Jianping; He, Yan‐Hong

doi:10.1016/j.tetlet.2012.07.007

Cited by 48 publications

(33 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“… a Reaction conditions: Cyclohexanone (2 mmol), malononitrile (4 mmol), benzaldehyde (2 mmol), enzyme (100 U), in solvent DMSO (5 ml) at 40 °C for 12 h, b Isolated yield, c PPL denatured by heating it to 100 °C for 6 h in ethanol, d PPL denatured with 50 mg urea in 2 ml water (0.83 M) at 100 °C for 24 h, e PPL pretreated with 50 mg PMSF in 2 ml THF (0.29 M) at 25 °C for 24 h, Nr: No Reaction. Np: No product formation…”

Section: Resultsmentioning

confidence: 99%

Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

et al. 2018

View full text Add to dashboard Cite

Enzymatic processes are highly specific, green, operate at mild conditions and reduce environmental pollution in comparison to conventional hazardous chemical processes. Herein, we describe a new strategy for the synthesis of ortho‐aminocarbonitriles by a multicomponent reaction of aromatic aldehydes, cyclohexanone and two equivalents of malononitrile at 40 °C. A new six‐membered ring was constructed by breaking seven bonds while four new bonds were formed. The solvent, lipase quantity and reaction conditions were optimized. The advantages of this biocatalyst mediated synthesis of ortho‐aminocarbonitriles comprised a one‐pot procedure with simple operations and higher yields, which were reported for the first time by biocatalysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

et al. 2018

View full text Add to dashboard Cite

show abstract

“…After the incubation period was over, Fractional inhibitory concentrations (ΣFICs) were calculated as follows: ΣFIC = FIC A + FIC B, where FIC A is the MIC of drug A in the combination/MIC of drug A alone and FIC B is the MIC of drug B in the combination/MIC of drug B alone. The combination is considered synergistic when the ∑FIC is ≤0.5, indifferent when the ∑FIC is >0.5 to 4, and antagonistic when the ∑FIC is >4 (Guan et al, ).…”

Section: Methodsmentioning

confidence: 99%

Biocatalytic synthesis of diaryl disulphides and their bio‐evaluation as potent inhibitors of drug‐resistant Staphylococcus aureus

Saima

Soni

Lavekar

et al. 2018

Drug Development Research

View full text Add to dashboard Cite

Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time‐kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi‐drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2‐bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration‐dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti‐staphylococcal therapy.

show abstract

“…Enzyme catalytic promiscuity is the "hidden skill" of the enzyme to catalyze different type of organic reactions [18][19][20][21][22][23][24][25]. This useful enzyme property makes it possible to catalyze multistep reactions in a multicomponent reaction (MCR).…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Synthesis of Indolyl 4H-Chromenes via a Multicomponent Reaction in Ionic Liquid

et al. 2017

View full text Add to dashboard Cite

Biocatalytic promiscuity: lipase-catalyzed asymmetric aldol reaction of heterocyclic ketones with aldehydes

Cited by 48 publications

References 34 publications

Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

Biocatalytic synthesis of diaryl disulphides and their bio‐evaluation as potent inhibitors of drug‐resistant Staphylococcus aureus

Lipase-Catalyzed Synthesis of Indolyl 4H-Chromenes via a Multicomponent Reaction in Ionic Liquid

Contact Info

Product

Resources

About