Yıl: 2018 Cilt: 5 Sayı: 2 Sayfa Aralığı: 737 - 750 Metin Dili: İngilizce DOI: 10.18596/jotcsa.414603 İndeks Tarihi: 22-02-2020

Enzyme-Catalyzed Trans-Benzoin Condensation

Öz:
Benzaldehyde lyase (BAL) is an enzyme that is used in the C-C bond cleavage andformation which was isolated first from Pseudomonas fluorescens Biovar I. It requires thiaminediphosphate (ThDP) and Mg(II) ions as cofactors. In this work, BAL was used as an enzymaticcatalyst for the trans-benzoin condensation reaction between racemic benzoins andbenzyloxyacetaldehyde to form unsymmetrical benzoin products with moderate enantiomericexcesses. (S)-benzoin derivatives remained unreacted at the end of the reaction. In thisenzymatic trans-benzoin condensation, benzyloxyacetaldehyde acted as acceptor and differentvariety of racemic benzoin derivatives were used as donor and (R)-2-hydroxy-1-phenylpropanone derivatives were synthesized up to 66% ee.
Anahtar Kelime:

Konular: Kimya, Analitik Termodinamik Spektroskopi Kimya, Uygulamalı Kimya, Organik Kimya, Tıbbi Fizikokimya Kimya, İnorganik ve Nükleer
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • Hinrichsen P, Gomez I, Vicuña R. Cloning and sequencing of the gene encoding benzaldehyde lyase from Pseudomonas fluorescens biovar I. Gene. 1994 Jun;144(1):137–8.
  • Biotransformations in organic chemistry: a textbook. 1st edition. Vol. 4. New York, NY: Springer Berlin Heidelberg; 1992.
  • Dünkelmann P, Kolter-Jung D, Nitsche A, Demir AS, Siegert P, Lingen B, et al. Development of a Donor−Acceptor Concept for Enzymatic Cross-Coupling Reactions of Aldehydes: The First Asymmetric Cross-Benzoin Condensation. Journal of the American Chemical Society. 2002 Oct;124(41):12084–5.
  • Demir AS, Ayhan P, Sopaci SB. Thiamine Pyrophosphate Dependent Enzyme Catalyzed Reactions: Stereoselective C–C Bond Formations in Water. CLEAN – Soil, Air, Water. 2007 Nov;35(5):406– 12.
  • Demir AS, Şeşenoglu Ö, Eren E, Hosrik B, Pohl M, Janzen E, et al. Enantioselective Synthesis of α-Hydroxy Ketones via Benzaldehyde Lyase-Catalyzed C−C Bond Formation Reaction. Advanced Synthesis & Catalysis. 2002 Jan;344(1):96.
  • Demir AS, Pohl M, Janzen E, Müller M. Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C–C bond cleavage. Journal of the Chemical Society, Perkin Transactions 1. 2001;(7):633–5.
  • Adams R, Marvel C. BENZOIN. Organic Syntheses. 1921;1:33.
  • Jin MY, Kim SM, Han H, Ryu DH, Yang JW. Switching Regioselectivity in Crossed Acyloin Condensations between Aromatic Aldehydes and Acetaldehyde by Altering N -Heterocyclic Carbene Catalysts. Organic Letters. 2011 Mar 4;13(5):880–3.
  • See supporting information for the HPLC chromatograms used to determine enantiomeric excesses.
APA BİLİR G, DEMİR A, Ozcubukcu S (2018). Enzyme-Catalyzed Trans-Benzoin Condensation. , 737 - 750. 10.18596/jotcsa.414603
Chicago BİLİR Gökçil,DEMİR Ayhan S.,Ozcubukcu Salih Enzyme-Catalyzed Trans-Benzoin Condensation. (2018): 737 - 750. 10.18596/jotcsa.414603
MLA BİLİR Gökçil,DEMİR Ayhan S.,Ozcubukcu Salih Enzyme-Catalyzed Trans-Benzoin Condensation. , 2018, ss.737 - 750. 10.18596/jotcsa.414603
AMA BİLİR G,DEMİR A,Ozcubukcu S Enzyme-Catalyzed Trans-Benzoin Condensation. . 2018; 737 - 750. 10.18596/jotcsa.414603
Vancouver BİLİR G,DEMİR A,Ozcubukcu S Enzyme-Catalyzed Trans-Benzoin Condensation. . 2018; 737 - 750. 10.18596/jotcsa.414603
IEEE BİLİR G,DEMİR A,Ozcubukcu S "Enzyme-Catalyzed Trans-Benzoin Condensation." , ss.737 - 750, 2018. 10.18596/jotcsa.414603
ISNAD BİLİR, Gökçil vd. "Enzyme-Catalyzed Trans-Benzoin Condensation". (2018), 737-750. https://doi.org/10.18596/jotcsa.414603
APA BİLİR G, DEMİR A, Ozcubukcu S (2018). Enzyme-Catalyzed Trans-Benzoin Condensation. Journal of the Turkish Chemical Society, Section A: Chemistry, 5(2), 737 - 750. 10.18596/jotcsa.414603
Chicago BİLİR Gökçil,DEMİR Ayhan S.,Ozcubukcu Salih Enzyme-Catalyzed Trans-Benzoin Condensation. Journal of the Turkish Chemical Society, Section A: Chemistry 5, no.2 (2018): 737 - 750. 10.18596/jotcsa.414603
MLA BİLİR Gökçil,DEMİR Ayhan S.,Ozcubukcu Salih Enzyme-Catalyzed Trans-Benzoin Condensation. Journal of the Turkish Chemical Society, Section A: Chemistry, vol.5, no.2, 2018, ss.737 - 750. 10.18596/jotcsa.414603
AMA BİLİR G,DEMİR A,Ozcubukcu S Enzyme-Catalyzed Trans-Benzoin Condensation. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(2): 737 - 750. 10.18596/jotcsa.414603
Vancouver BİLİR G,DEMİR A,Ozcubukcu S Enzyme-Catalyzed Trans-Benzoin Condensation. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(2): 737 - 750. 10.18596/jotcsa.414603
IEEE BİLİR G,DEMİR A,Ozcubukcu S "Enzyme-Catalyzed Trans-Benzoin Condensation." Journal of the Turkish Chemical Society, Section A: Chemistry, 5, ss.737 - 750, 2018. 10.18596/jotcsa.414603
ISNAD BİLİR, Gökçil vd. "Enzyme-Catalyzed Trans-Benzoin Condensation". Journal of the Turkish Chemical Society, Section A: Chemistry 5/2 (2018), 737-750. https://doi.org/10.18596/jotcsa.414603