scholarly journals Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis

2021 ◽  
Author(s):  
Nitai Arbell ◽  
Kesem Bauer ◽  
Yaron Paz
Keyword(s):  
Kinetic Resolution ◽  
Racemic Mixtures

scholarly journals Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1019
Author(s):  
Martins Rucins ◽  
Aiva Plotniece ◽  
Eiva Bernotiene ◽  
Wei-Bor Tsai ◽  
Arkadij Sobolev
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Biological Activities ◽  
Great Promise ◽  
Racemic Mixtures ◽  
Treatment Of Hypertension ◽  
Opposite Action ◽  
Recent Developments ◽  
Substantial Progress ◽  
Active Calcium

The purpose of this review is to highlight recent developments in the synthesis of chiral 1,4-dihydropyridines and their fused analogues. 1,4-Dihydropyridines are among the most active calcium antagonists that are used for the treatment of hypertension. Enantiomers of unsymmetrical 1,4-dihydropyridines often show different biological activities and may have even an opposite action profile. Hantzsch synthesis usually produces racemic mixtures of unsymmetrical 1,4-dihydropyridines. Therefore, the development of stereoselective synthesis of 1,4-dihydropyridines is one of the priorities of medicinal chemistry. Over the years, numerous methodologies have been developed for the production of enantiopure 1,4-dihydropyridines, such as stereoselective synthesis using chiral auxiliaries and chiral cyclocondensation partners, chromatographical methods, resolution of diastereomeric 1,4-dihydropyridine salts, enzyme catalysed kinetic resolution, or asymmetrisation of ester groups of 1,4-dihydropyridines. These approaches have been studied in detail and are relatively well established. The catalytic asymmetric approach holds the greatest promise in delivering the most practical and widely applicable methods. Substantial progress has been made toward the development of enantioselective organocatalytic methods for the construction of the chiral dihydropyridines. However, most of them do not provide a convenient way to pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates. Organocatalytic enantioselective desymmetrisation of prochiral 1,4-dihydropyridine-3,5-dicarbaldehydes also has great promise in the synthesis of pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates.

Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids

2013 ◽  
Vol 91 ◽  
pp. 32-36 ◽  
Author(s):  
Kinga Kozyra ◽  
Małgorzata Brzezińska-Rodak ◽  
Magdalena Klimek-Ochab ◽  
Ewa Żymańczyk-Duda
Keyword(s):  
Kinetic Resolution ◽  
Aminophosphonic Acids ◽  
Racemic Mixtures

Kinetic resolution of 2-hydroxybutanoate racemic mixtures by NAD-independent l-lactate dehydrogenase

2011 ◽  
Vol 102 (7) ◽  
pp. 4595-4599 ◽  
Author(s):  
Chao Gao ◽  
Wen Zhang ◽  
Cuiqing Ma ◽  
Peng Liu ◽  
Ping Xu
Keyword(s):  
Lactate Dehydrogenase ◽  
Kinetic Resolution ◽  
Racemic Mixtures

scholarly journals Phosphonates enantiomers receiving with fungal enzymatic systems

2021 ◽  
Vol 20 (1) ◽  
Author(s):  
Monika Serafin-Lewańczuk ◽  
Małgorzata Brzezińska-Rodak ◽  
Katarzyna Lubiak-Kozłowska ◽  
Paulina Majewska ◽  
Magdalena Klimek-Ochab ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Nutrient Deficiency ◽  
Methylphosphonic Acid ◽  
Racemic Mixture ◽  
Biological Interactions ◽  
Racemic Mixtures ◽  
Enzymatic Systems ◽  
Pre Treatment ◽  
Physical Features ◽  
First Time

Abstract Background Phosphonates derivatives are in the area of interests because of their unique chemical-physical features. These compounds manifest variety of biological interactions within the sensitive living cells, including impact on particular enzymes activities. Biological “cause and effect” interactions are based upon the specific matching between the structures and/or compounds and this is usually the result of proper optical configurations of particular chiral moieties. Presented research is targeted to the phosphonates with the heteroatom incorporated in their side functionalities. Such molecules are described as possible substrates of bioconversion for the first time lately and this field is not fully explored. Results Presented research is targeted to the synthesis of pure hetero-phosphonates enantiomers. The catalytic activity of yeasts and moulds were tested towards two substrates: the thienyl and imidazole phosphonates to resolve their racemic mixtures. Biotransformations conditions differed depending on the outcome, what included changing of following parameters: type of cultivation media, bioprocess duration (24–72 h), additional biocatalyst pre-treatment (24–48 h starvation step triggering the secondary metabolism). (S)-1-amino-1-(3-thienyl)methylphosphonate was produced with the assistance of R. mucilaginosa or A. niger (e.e. up to 98% and yield up to 100%), starting from the 3 mM of substrate racemic mixture. Bioconversion of racemic mixture of 3 mM of (1-amino-1-(4-imidazole)methylphosphonic acid) resulted in the synthesis of S-isomer (up to 95% of e.e.; 100% of yield) with assistance of R. mucilaginosa. 24 h biotransformation was conducted with biomass preincubated under 48-hour starvation conditions. Such stereoselective resolution of the racemic mixtures of substrates undergoes under kinetic control with the conversion of one from the enantiomers. Conclusions Composition of the culturing media and pre-incubation in conditions of nutrient deficiency were significant factors influencing the results of kinetic resolution of racemic mixtures of phosphonic substrates and influencing the economic side of the biocatalysis e.g. by determining the duration of whole biocatalytic process. Graphical abstract

scholarly journals Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures

Molecules ◽  
2016 ◽  
Vol 21 (11) ◽  
pp. 1552 ◽  
Author(s):  
Andrzej Skrobiszewski ◽  
Witold Gładkowski ◽  
Gabriela Maciejewska ◽  
Czesław Wawrzeńczyk
Keyword(s):  
Kinetic Resolution ◽  
Chemoenzymatic Synthesis ◽  
Enzymatic Kinetic Resolution ◽  
Racemic Mixtures

Lipase-Catalyzed Kinetic Resolution of the Racemic Mixtures of 1-Aryloxy-3-Nitrato-and 1-Aryloxy-3-Azido-2-Propanols

1998 ◽  
Vol 28 (23) ◽  
pp. 4355-4364 ◽  
Author(s):  
Beata Pchelka ◽  
Justyna Radomska ◽  
Jan Plenkiewicz
Keyword(s):  
Kinetic Resolution ◽  
Racemic Mixtures
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