Öz
Kaynakça
- 1. 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.
- 2. Biotransformations in organic chemistry: a textbook. 1st edition. Vol. 4. New York, NY: Springer Berlin Heidelberg; 1992.
- 3. 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.
- 4. 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.
- 5. 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.
- 6. 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.
- 7. Adams R, Marvel C. BENZOIN. Organic Syntheses. 1921;1:33.
- 8. 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.
- 9. See supporting information for the HPLC chromatograms used to determine enantiomeric excesses.
Öz
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.
Anahtar Kelimeler
Benzaldehyde lyase benzoin condensation enzymatic asymmetric catalysis
Kaynakça
- 1. 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.
- 2. Biotransformations in organic chemistry: a textbook. 1st edition. Vol. 4. New York, NY: Springer Berlin Heidelberg; 1992.
- 3. 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.
- 4. 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.
- 5. 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.
- 6. 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.
- 7. Adams R, Marvel C. BENZOIN. Organic Syntheses. 1921;1:33.
- 8. 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.
- 9. See supporting information for the HPLC chromatograms used to determine enantiomeric excesses.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Kimya Mühendisliği |
| Bölüm | Makaleler |
| Yazarlar | |
| Yayımlanma Tarihi | 1 Ocak 2018 |
| Gönderilme Tarihi | 12 Nisan 2018 |
| Kabul Tarihi | 28 Nisan 2018 |
| Yayımlandığı Sayı | Yıl 2018 Cilt: 5 Sayı: 2 |
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