Synthetic studies aimed at preparation of caramboxina, an alpha-amino acid with potential biological activity.

Author(s)

Leandro Alves Bozzini

• Document type: Master's Dissertation
• Press: Ribeirão Preto.
• Institution: Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto (PCARP/BC)
• Defense date: 2015-06-12

Examining board members

Giuliano Cesar Clososki; Amanda Danuello Pivatto; Cristiano Raminelli

• Advisor: Giuliano Cesar Clososki

Abstract

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. (AU)

• FAPESP's process: 13/01388-2 - Synthetic Studies Aiming the Preparation of alpha amino acids with Potential Biological Activity
• Grantee: Leandro Alves Bozzini
• Support Opportunities: Scholarships in Brazil - Master