Carboligation reactions with benzaldehyde lyase immobilized on superparamagnetic solid support

2009-01-01
Sopaci, S. Betuel
Turan, Ilke Simsek
Tural, Bilsen
Volkan, Mürvet
Demir, Ayhan Sıtkı
Histidine-tagged recombinant benzaldehyde lyase (BAL, EC 4.1.2.38) was efficiently immobilized to surface-modified magnetic particles with affinity ligand binding. In addition to conventional benzoin condensation reactions, two important representative BAL-catalyzed carboligation reactions, were also performed with this magnetically responsive biocatalyst. The results obtained from the carboligation reactions that were performed with this simple and convenient heterogenous biocatalyst were comparable to that of free-enzyme-catalyzed reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY

Suggestions

Benzaldehyde lyase catalyzed enantioselective self and cross condensation reactions of acetaldehyde derivatives
Ayhan, Peruze; Turan, Ilke Simsek; Cifci, Burce; Demir, Ayhan Sıtkı (Royal Society of Chemistry (RSC), 2011-01-01)
Flexible protected 1,3,4-trihydroxy-2-butanone is synthesized in high enantiomeric excesses by using asymmetric homo- and cross- acyloin coupling of aliphatic aldehydes catalyzed by benzaldehyde lyase.
Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde
Demir, Ayhan Sıtkı; Sesenoglu, O; Dunkelmann, P; Muller, M (American Chemical Society (ACS), 2003-06-12)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Bifunctional squaramide catalyzed stereoselective Mannich reaction of alpha-azido ketones with isatin-derived ketimines
KARAHAN, SEDA; Tanyeli, Cihangir (Royal Society of Chemistry (RSC), 2020-01-21)
Asymmetric organocatalytic Mannich reaction of alpha-azido ketones and N-Boc protected isatin-derived ketimines were investigated for the first time. Examination of both 2-adamantyl and 3,5-bis(trifluoromethyl)aniline substituted quinine-based squaramides afforded chiral Mannich bases with two contiguous stereogenic centers in high yields (up to 97%) and stereoselectivity (up to dr = 24 : 1 syn : anti and 96% ee). Azido and masked amino functionalities of the potent heterocycle precursor adducts were utiliz...
Regioselective Synthesis of Benzo[h][1,6]- naphthyridines and Chromenopyrazinones through Alkyne Cyclization
Hoplamaz, Emre; KESKİN, SELBİ; Balcı, Metin (Wiley, 2017-03-17)
A regioselective approach to the synthesis of benzo[h][1,6]-naphthyridine and chromenopyrazinone derivatives was developed. The synthetic route to benzo[h][1,6]naphthyridines involves the N-propargylation of aromatic aminobenzaldehydes, followed by reaction with propargylamine in the presence of DBU (1,8-diazabicyclo[5.4.0] undec-7ene). For the synthesis of chromenopyrazine and chromeno-pyrazinone derivatives, the acetonitrile group was introduced to salicylaldehyde derivatives, and a DBU-promoted cyclizati...
Synthesis of ferrocenyl quinolines
Zora, Metin (Elsevier BV, 2008-06-01)
A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.
Citation Formats
S. B. Sopaci, I. S. Turan, B. Tural, M. Volkan, and A. S. Demir, “Carboligation reactions with benzaldehyde lyase immobilized on superparamagnetic solid support,” ORGANIC & BIOMOLECULAR CHEMISTRY, pp. 1658–1664, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36935.