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Master's Dissertation
DOI
Document
Author
Full name
Leandro Alves Bozzini
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
Ribeirão Preto, 2015
Supervisor
Committee
Clososki, Giuliano Cesar (President)
Pivatto, Amanda Danuello
Raminelli, Cristiano
Title in Portuguese
Estudos sintéticos visando à preparação da caramboxina, um alfa-aminoácido com potencial atividade biológica
Keywords in Portuguese
Aminoácidos
Carambola
Caramboxina
Organometálicos
Abstract in Portuguese
Em 2005, Carolino e colaboradores isolaram uma fração neurotóxida de Averrhoa carambola (carambola) que foi capaz de apresentar sintomas em ratos e camundongos e foi chamada de AcTx. Acredita-se que o aminoácido denominado caramboxina esteja presente nesta fração e seja o metabólito secundário responsável por envenenamento pela ingestão da fruta em pacientes com insuficiência renal crônica. Apesar da estrutura da caramboxina ter sido elucidada por análises espectrométricas, a síntese deste composto visando caracterização estrutural e análise biológica ainda não havia sido realizada. Assim o objetivo deste trabalho foi investigar a síntese total da caramboxina visando sua caracterização estrutural e análise biológica dos compostos obtidos. Quatro rotas foram propostas, três das quais fizeram uso de reagentes organometálicos. Aquela que não fez uso de reagentes organometálicos foi a que se mostrou mais eficiente.
Title in English
Synthetic studies aimed at preparation of caramboxina, an alpha-amino acid with potential biological activity.
Keywords in English
Amino acids
Caramboxine
Organometalics
Star fruit
Abstract in English
In 2005, Carolino and co-workers isolated a neurotoxic fraction of Averrhoa carambola (star fruit) that was able to cause seizures in rats and mice and was named AcTx. It is believed that the amino acid caramboxine, present in this fraction, is one of the secondary metabolites responsible for poisoning by fruit intake by patients with chronic renal failure. Despite its structure has been elucidated by spectrometric analysis, the synthesis of this compound aiming structural characterization and biological evaluation has not been still accomplished. Thus, the objective of this project was the total synthesis of caramboxina aiming their structural characterization and biological testing of the compounds obtained. Four routes have been proposed and investigated, three of them using organometallic reagents. The route that didn't use organometallic intermediates appeared to be the most efficient.
 
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Release Date
2019-08-12
Publishing Date
2015-10-20
 
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