title: Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I.
abstract: Intramolecular benzoin reactions catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I (BAL) are reported. The structure of the substrates envisaged for this reaction consists of two benzaldehyde derivatives linked by an alkyl chain. The structural requirements needed to achieve the intramolecular carbon-carbon bond reaction catalyzed by BAL were established. Thus, a linker consisting of a linear alkyl chain of three carbon atoms connected through ether-type bonds to the 2 and 2' positions of two benzaldehyde moieties, which could be substituted with either Cl, Br, or OCH3at either the 3 and 3' or 5 and 5' positions, were suitable substrates for BAL. Reactions with 61-84 % yields of the intramolecular product and ee values between 64 and 98 %, were achieved.
authors.affiliation: Catalonia Institute for Advanced Chemistry, Dept. Chemical Biology & Molecular Modelling, IQAC-CSIC, Jordi Girona 18-26, 08034, Barcelona, Spain.
authors.forename: Karel
authors.initials: K
authors.lastname: Hernández
authors.affiliation: Servei de Ressonáncia Magnética Nuclear, Universitat Autònoma de Barcelona, Bellaterra, Spain.
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
authors.affiliation: Dept. Chemical Biology & Molecular Modelling, Instituto de Química Avanzada de Cataluña, IQAC-CSIC, Instituto de Biología Molecular de Barcelona, IBMB-CSIC, Spain.
authors.forename: Giovanna
authors.initials: G
authors.lastname: Petrillo
authors.affiliation: Instituto de Biología Molecular de Barcelona, IBMB-CSIC, Institució Catalana de Recerca i Estudis Avançats (ICREA), Spain.
authors.forename: Isabel
authors.initials: I
authors.lastname: Usón
authors.affiliation: Institut für Anorganische Chemie, Universität Göttingen, Göttingen, Germany.
authors.forename: Claudia M
authors.initials: CM
authors.lastname: Wandtke
authors.affiliation: Catalonia Institute for Advanced Chemistry, Dept. Chemical Biology & Molecular Modelling, IQAC-CSIC, Jordi Girona 18-26, 08034, Barcelona, Spain.
authors.forename: Jesús
authors.identifier: 0000-0002-3391-1682
authors.initials: J
authors.lastname: Joglar
authors.affiliation: Catalonia Institute for Advanced Chemistry, Dept. Chemical Biology & Molecular Modelling, IQAC-CSIC, Jordi Girona 18-26, 08034, Barcelona, Spain.
authors.forename: Jordi
authors.initials: J
authors.lastname: Bujons
authors.affiliation: Catalonia Institute for Advanced Chemistry, Dept. Chemical Biology & Molecular Modelling, IQAC-CSIC, Jordi Girona 18-26, 08034, Barcelona, Spain.
authors.forename: Pere
authors.identifier: 0000-0001-5541-4794
authors.initials: P
authors.lastname: Clapés
mesh_terms: D000446:Aldehyde-Lyases / Q000378:metabolism*; D001573:Benzoin / Q000737:chemistry / Q000378:metabolism*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011551:Pseudomonas fluorescens / Q000201:enzymology*
chemical_list: D000446:Aldehyde-Lyases; C059416:benzaldehyde lyase; D001573:Benzoin
keywords: C−C coupling; asymmetric catalysis; biocatalysis; enzymes; macrocycles