Enzyme Catalyzed Trans-Benzoin Condensation

BİLİR, Gökçil
Özçubukçu, Salih
Benzaldehyde lyase (BAL) is an enzyme that is used in the C-C bond cleavage and formation which was isolated first from Pseudomonas fluorescens Biovar I. It requires thiamine diphosphate (ThDP) and Mg(II) ions as cofactors. In this work, BAL was used as an enzymatic catalysis for the trans-benzoin condensation reaction between racemic benzoins and benzyloxyacetaldehyde to form unsymmetrical benzoin products with moderate enantiomeric excesses. (S)-benzoin derivatives remained unreacted at the end of the reaction. In this enzymatic trans-benzoin condensation, benzyloxyacetaldeyhde acted as acceptor and different variety of racemic benzoin derivatives were used as donor and (R)-2-hydroxy-1-phenylpropanone derivatives were synthesized up to 66% ee.
Journal of the Turkish Chemical Society, Section A: Chemistry


Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C-C bond cleavage
Demir, Ayhan Sıtkı; Pohl, M; Janzen, E; Muller, M (2001-01-01)
Both enantiomers of benzoins and (R)-2-hydroxy-1-phenylpropanone analogues were obtained in high yield on a preparative scale starting from aromatic aldehydes, rac-benzoins and aliphatic aldehydes via enzyme-catalysed C-C bond cleavage and C-C bond formation reactions.
Fungal deracemization of benzoin
Demir, AS; Hamamcı, Haluk; Sesenoglu, O; Neslihanoglu, R; Asikoglu, B; Capanoglu, D (2002-09-02)
An enzyme system of Rhizopus oryzae (ATCC 9363) catalyzes the inversion of the chirality of benzoin via a deracemization reaction and, depending on the pH of the medium, both enantiomers of benzoin are obtained in good yield and high ee starting from rac-benzoin.
Amination/annulation of chlorobutenones with chiral amine compounds: synthesis of 1,2,4-trisubstituted pyrroles
Demir, Ayhan Sıtkı; Igdir, AC; Gunay, NB (Elsevier BV, 2005-10-03)
A series of 1,2,4-trisubstituted pyrroles have been synthesized in 83-96% yields on treatment of chiral primary amines, amino alcohols and esters of alpha-amino acids with different chlorobutenones in benzene-triethylamine. The conversions proceed without racemization.
Cloning and expression ofbenzaldehydelyase from Pseudomonas fluorescens Biovar I in Pichia pastoris
Büyüksungur, Arda; Çalık, Pınar; Department of Biotechnology (2006)
Benzaldehyde lyase (BAL, EC from Pseudomonas fluorescens Biovar I, a thiamine pyrophosphate (ThDP) dependent enzyme, catalyzes the enzymatic kinetic resolution of racemates by C-C bond cleavage and concomitant C-C bond formation. In this study, benzaldehyde lyase gene from Pseudomonas fluorescens Biovar I was cloned into Pichia pastoris, with the aim of the extracellular production of the enzyme. For this purpose, firstly, PCR amplified bal gene was cloned into an integration vector pPICZalphaA. T...
Synthesis of new mediators for electrochemical nad/nadh recycling
Khalily, Mohammad Aref; Demir, Ayhan Sıtkı; Department of Chemistry (2011)
The synthesis of enantiopure compounds can be achieved by using dehydrogenases as biocatalysts. For instance, reduction reactions of prochiral compounds (ketones, aldehydes and nitriles) into chiral compounds can be achieved by dehydrogenases. These dehydrogenases are cofactor dependent where cofactor is Nicotinamide Adenin Dinucleotite having some restrictions that confines usage of dehydrogenases in organic synthesis including instability of cofactor in water and high cost. Therefore, suitable recycling m...
Citation Formats
G. BİLİR, D. AYHAN SITKI, and S. Özçubukçu, “Enzyme Catalyzed Trans-Benzoin Condensation,” Journal of the Turkish Chemical Society, Section A: Chemistry, pp. 737–750, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41941.