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Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.

The thiamine diphosphate (ThDP) dependent enzyme acetoin:dichlorophenolindophenol oxidoreductase (Ao:DCPIP?OR) from Bacillus licheniformis was cloned and overexpressed in Escherichia coli. The recombinant enzyme shared close similarities with the acetylacetoin synthase (AAS) partially purified from...

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Autor Principal: Bernacchia, Giovanni
Formato: Artículos
Lenguaje:eng
Publicado: 2016
Materias:
ASYMMETRIC SYNTHESIS
ENZYME CATALYSIS
OXIDOREDUCTASES
TERTIARY ALCOHOLS
Acceso en línea:http://repositorio.educacionsuperior.gob.ec/handle/28000/3019
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spelling oai:localhost:28000-30192017-04-17T15:34:06Z Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin. Bernacchia, Giovanni ASYMMETRIC SYNTHESIS ENZYME CATALYSIS OXIDOREDUCTASES TERTIARY ALCOHOLS The thiamine diphosphate (ThDP) dependent enzyme acetoin:dichlorophenolindophenol oxidoreductase (Ao:DCPIP?OR) from Bacillus licheniformis was cloned and overexpressed in Escherichia coli. The recombinant enzyme shared close similarities with the acetylacetoin synthase (AAS) partially purified from Bacillus licheniformis suggesting that they could be the same enzyme. The product scope of the recombinant Ao:DCPIP?OR was expanded to chiral tertiary ?-hydroxy ketones through the rare aldehyde-ketone cross-carboligation reaction. Unprecedented is the use of methylacetoin as the acetyl anion donor in combination with a range of strongly to weakly activated ketones. In some cases, Ao:DCPIP?OR produced the desired tertiary alcohols with stereochemistry opposite to that obtained with other ThDP-dependent enzymes. The combination of methylacetoin as acyl anion synthon and novel ThDP-dependent enzymes considerably expands the available range of C-C bond formations in asymmetric synthesis. Universidad Polit?cnica Salesiana https://www.ncbi.nlm.nih.gov/pubmed/25914187 2016-11-09T16:31:06Z 2016-11-09T16:31:06Z 2015 article Bernacchia, Giovanni. et al. (2015). Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin. Angewandte Chemie - International Edition Volume 127. pp. 7277?7281 1521-3773 http://repositorio.educacionsuperior.gob.ec/handle/28000/3019 eng openAccess pp. 7277?7281
institution SENESCYT
collection Repositorio SENESCYT
biblioteca Biblioteca Senescyt
language eng
format Artículos
topic ASYMMETRIC SYNTHESIS
ENZYME CATALYSIS
OXIDOREDUCTASES
TERTIARY ALCOHOLS
spellingShingle ASYMMETRIC SYNTHESIS
ENZYME CATALYSIS
OXIDOREDUCTASES
TERTIARY ALCOHOLS
Bernacchia, Giovanni
Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
description The thiamine diphosphate (ThDP) dependent enzyme acetoin:dichlorophenolindophenol oxidoreductase (Ao:DCPIP?OR) from Bacillus licheniformis was cloned and overexpressed in Escherichia coli. The recombinant enzyme shared close similarities with the acetylacetoin synthase (AAS) partially purified from Bacillus licheniformis suggesting that they could be the same enzyme. The product scope of the recombinant Ao:DCPIP?OR was expanded to chiral tertiary ?-hydroxy ketones through the rare aldehyde-ketone cross-carboligation reaction. Unprecedented is the use of methylacetoin as the acetyl anion donor in combination with a range of strongly to weakly activated ketones. In some cases, Ao:DCPIP?OR produced the desired tertiary alcohols with stereochemistry opposite to that obtained with other ThDP-dependent enzymes. The combination of methylacetoin as acyl anion synthon and novel ThDP-dependent enzymes considerably expands the available range of C-C bond formations in asymmetric synthesis.
author Bernacchia, Giovanni
author_facet Bernacchia, Giovanni
author_sort Bernacchia, Giovanni
title Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
title_short Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
title_full Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
title_fullStr Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
title_full_unstemmed Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin.
title_sort enzymatic chemoselective aldehyde-ketone cross-couplings through the polarity reversal of methylacetoin.
publishDate 2016
url http://repositorio.educacionsuperior.gob.ec/handle/28000/3019
_version_ 1634995101348397056
score 11,871979

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