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Master's Dissertation
DOI
10.11606/D.46.2009.tde-05102009-094753
Document
Author
Full name
Joel Savi dos Reis
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2009
Supervisor
Committee
Comasseto, João Valdir (President)
Andrade, Leandro Helgueira
Ludtke, Diogo Seibert
Title in Portuguese
Resolução cinética enzimática de hidroxiésteres propargílicos: uma via de obtenção de moléculas bioativas
Keywords in Portuguese
Catálise
Cinética química
Enzimas
Hidroxiésteres
Moléculas Bioativas
Resolução Cinética Enzimática
Síntese orgânica
Abstract in Portuguese
A obtenção de moléculas enantiomericamente puras ou enriquecidas tem se demonstrado um desafio em química orgânica sintética. Nesse âmbito, a biocatálise aparece como uma importante ferramenta sintética. Neste trabalho, desenvolveu-se uma metodologia para a obtenção de 6-hidróxioct-7-inoato de metila, 5-hidróxihept-6-inoato de metila, e 4-hidróxihex-5-inoato de metila enantiomericamente enriquecidos via resolução cinética enzimática. Primeiramente foram investigadas variáveis como temperatura, tempo, quantidade de doador de acila, solvente e enzima adequada para a reação. Em uma segunda etapa do trabalho, foram desenvolvidas seqüências reacionais onde os hidroxiésteres originariam moléculas bioativas Utilizando o 5-hidróxihept-6-inoato de metila, após três etapas reacionais, foi possível sintetizar intermediários sintéticos avançados das moléculas bioativas goniotalamina e argentilactona. De maneira análoga, após algumas etapas reacionais, o 4-hidróxihex-5-inoato de metila originou os feromônios buibuilactona, japonilura e 4-hexanolida
Title in English
Hidroxiésteres, Resolução Cinética Enzimática, Moléculas Bioativas
Keywords in English
Bioactive Molecules
Catalysis
Enzymatic Kinetic Resolution
Enzymes
Hydroxyesters
Organic synthesis
Abstract in English
The synthesis of enantiomerically pure or enriched molecules has been an important challenge in synthetic organic chemistry. Among a variety of disciplines dedicated to achive this goal, biocatalysis appears as an important synthetic tool. Herein, we developed a methodology to obtain methyl 6-hydroxyoct-7-ynoate, methyl 5-hydroxyhept-6-ynoate and methyl 4-hydroxyhex-5-ynoate enantiomerically enriched by an enzymatic kinetic resolution. Reaction conditions such as temperature, reaction time, amount of acyl donor, solvent and enzyme were screened, in order to obtain high yields and enantioselectivities. In the second part of our work, synthetic pathways were developed where the hydroxyesters lead to bioactive molecules. Using methyl 5-hydroxyhept-6-ynoate, after three steps, advanced synthetic intermediates for the synthesis of the bioactive molecules, such as goniothalamine and argentilactone, were prepared. In the same way, methyl 4-hydroxyhex-5-ynoate was submitted to a reaction sequence leading the pheromones buibuilactone, japonilure and 4-hexanolide.
 
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ErrataJoelSaviReis.pdf (10.00 Kbytes)
Publishing Date
2010-04-14
 
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