Miguel Lara - Academia.edu (original) (raw)
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Papers by Miguel Lara
Tetrahedron, 2007
The oxidative cleavage of a CC double bond adjacent to an aryl moiety was achieved in the presenc... more The oxidative cleavage of a CC double bond adjacent to an aryl moiety was achieved in the presence of a protein preparation of Trametes hirsuta G FCC 047 to yield the corresponding aldehydes. Molecular oxygen was the only oxidant required. All positive substrates had a CC bond conjugated to an aromatic system, all other compounds tested not fulfilling this requirement
Journal of the American Chemical Society, 2009
Enzymatic alkene cleavage by incorporation of two oxygen atoms is described to occur either follo... more Enzymatic alkene cleavage by incorporation of two oxygen atoms is described to occur either following a dioxygenase 1,2 or a monooxygenase 3 mechanism. In case of a monooxygenase mechanism, one oxygen atom in the cleavage product(s) originates from water and one from molecular oxygen. On the other hand, both oxygen atoms of one molecule O 2 are incorporated in the dioxygenase pathway via a dioxetane or related 1,2-dioxo-cyclic intermediate. We report here that mechanistic investigations of the alkene JA8097096 Scheme 2. Proposed Alternative Enzymatic Mechanism for Alkene Cleavage
Journal of Molecular Catalysis B: Enzymatic, 2009
Two different biocatalytic reactions-a C C cleavage and a C C forming reaction-were evaluated con... more Two different biocatalytic reactions-a C C cleavage and a C C forming reaction-were evaluated concerning their application in a reaction sequence. In the overall reaction, an aromatic alkene was converted to a chiral 2-hydroxy ketone. In the first step, the olefin trans-anethole was converted to para-anisaldehyde and acetaldehyde by an aqueous extract of the white rot fungus Trametes hirsuta G FCC 047. The selective oxidative cleavage of the carbon-carbon double bond was achieved using molecular oxygen as a substrate. In a second step p-anisaldehyde was ligated to acetaldehyde to yield either (R)-or (S)-2-hydroxy-1-(4-methoxyphenyl)-propanone. The reaction was catalyzed by the enantiocomplementary C C bond forming enzymes benzaldehyde lyase and benzoylformate decarboxylase, respectively.
Angewandte Chemie International Edition, 2006
Biochemical syntheses O 0035 Biocatalytic Single-Step Alkene Cleavage from Aryl Alkenes: An Enzym... more Biochemical syntheses O 0035 Biocatalytic Single-Step Alkene Cleavage from Aryl Alkenes: An Enzymatic Equivalent to Reductive Ozonization.-The method offers a simple and environmentally friendly method to prepare aromatic aldehydes and ketones.-(MANG, H.;
Advanced Synthesis & Catalysis, 2013
Tetrahedron, 2007
The oxidative cleavage of a CC double bond adjacent to an aryl moiety was achieved in the presenc... more The oxidative cleavage of a CC double bond adjacent to an aryl moiety was achieved in the presence of a protein preparation of Trametes hirsuta G FCC 047 to yield the corresponding aldehydes. Molecular oxygen was the only oxidant required. All positive substrates had a CC bond conjugated to an aromatic system, all other compounds tested not fulfilling this requirement
Journal of the American Chemical Society, 2009
Enzymatic alkene cleavage by incorporation of two oxygen atoms is described to occur either follo... more Enzymatic alkene cleavage by incorporation of two oxygen atoms is described to occur either following a dioxygenase 1,2 or a monooxygenase 3 mechanism. In case of a monooxygenase mechanism, one oxygen atom in the cleavage product(s) originates from water and one from molecular oxygen. On the other hand, both oxygen atoms of one molecule O 2 are incorporated in the dioxygenase pathway via a dioxetane or related 1,2-dioxo-cyclic intermediate. We report here that mechanistic investigations of the alkene JA8097096 Scheme 2. Proposed Alternative Enzymatic Mechanism for Alkene Cleavage
Journal of Molecular Catalysis B: Enzymatic, 2009
Two different biocatalytic reactions-a C C cleavage and a C C forming reaction-were evaluated con... more Two different biocatalytic reactions-a C C cleavage and a C C forming reaction-were evaluated concerning their application in a reaction sequence. In the overall reaction, an aromatic alkene was converted to a chiral 2-hydroxy ketone. In the first step, the olefin trans-anethole was converted to para-anisaldehyde and acetaldehyde by an aqueous extract of the white rot fungus Trametes hirsuta G FCC 047. The selective oxidative cleavage of the carbon-carbon double bond was achieved using molecular oxygen as a substrate. In a second step p-anisaldehyde was ligated to acetaldehyde to yield either (R)-or (S)-2-hydroxy-1-(4-methoxyphenyl)-propanone. The reaction was catalyzed by the enantiocomplementary C C bond forming enzymes benzaldehyde lyase and benzoylformate decarboxylase, respectively.
Angewandte Chemie International Edition, 2006
Biochemical syntheses O 0035 Biocatalytic Single-Step Alkene Cleavage from Aryl Alkenes: An Enzym... more Biochemical syntheses O 0035 Biocatalytic Single-Step Alkene Cleavage from Aryl Alkenes: An Enzymatic Equivalent to Reductive Ozonization.-The method offers a simple and environmentally friendly method to prepare aromatic aldehydes and ketones.-(MANG, H.;
Advanced Synthesis & Catalysis, 2013