One‐Pot Cascade Synthesis of (3S)‐Hydroxyketones Catalyzed by TransketolaseviaHydroxypyruvate Generatedin Situfromd ‐Serine byd ‐Amino Acid Oxidase
| العنوان: | One‐Pot Cascade Synthesis of (3S)‐Hydroxyketones Catalyzed by TransketolaseviaHydroxypyruvate Generatedin Situfrom |
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| المؤلفون: | Nazim Ocal, Laurence Hecquet, Mélanie L’enfant, Marion Lorillière, Loredano Pollegioni, Wolf-Dieter Fessner, Felipe Bruna, Franck Charmantray |
| المساهمون: | Institut de Chimie de Clermont-Ferrand (ICCF), SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Centre National de la Recherche Scientifique (CNRS), Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Darmstadt, Universitá degli Studi dell’Insubria = University of Insubria [Varese] (Uninsubria), Department of Biotechnology and Life Sciences, Università degli Studi dell'Insubria, Varese |
| المصدر: | Advanced Synthesis and Catalysis Advanced Synthesis and Catalysis, 2019, 361, pp.2550-2558. ⟨10.1002/adsc.201900109⟩ Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2019, 361, pp.2550-2558. ⟨10.1002/adsc.201900109⟩ |
| بيانات النشر: | Wiley, 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Oxidase test, biocatalysis, 010405 organic chemistry, Transamination, Stereochemistry, D-amino acid oxidase, Substrate (chemistry), General Chemistry, Transketolase, stereoselectivity, 010402 general chemistry, 01 natural sciences, Chemical synthesis, 0104 chemical sciences, d-amino acid oxidase, hydroxypyruvate, ketoses, transketolase, chemistry, Cascade reaction, Biocatalysis, [CHIM]Chemical Sciences |
| الوصف: | International audience; We described an efficient in situ generation of hydroxypyruvate from d‐serine catalyzed by a d‐amino acid oxidase from Rhodotorula gracilis. This strategy revealed an interesting alternative to the conventional chemical synthesis of hydroxypyruvate starting from toxic bromopyruvate or to the enzymatic transamination from l‐serine requiring an additional substrate as amino acceptor. Hydroxypyruvate thus produced was used as donor substrate of transketolases from Escherichia coli or from Geobacillus stearothermophilus catalyzing the stereoselective formation of a carbon−carbon bond. The enzymatic cascade reaction was performed in one‐pot in the presence of d‐serine and appropriate aldehydes for the synthesis of valuable (3S)‐hydroxyketones, which were obtained with high enantio‐ and diastereoselectivity and in good yield. The efficiency of the process was based on the irreversibility of both reactions allowing complete conversion of d‐serine and aldehydes. |
| تدمد: | 1615-4169 1615-4150 |
| DOI: | 10.1002/adsc.201900109 |
| DOI: | 10.1002/adsc.201900109⟩ |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::01785e5d57b2ac9a1ebebfd3024dbdaf https://doi.org/10.1002/adsc.201900109 |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....01785e5d57b2ac9a1ebebfd3024dbdaf |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 16154169 16154150 |
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| DOI: | 10.1002/adsc.201900109 |