New catalytic reactions for the construction of peptides and carbohydrate hybrids

• Grant number: 14/16516-9
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• Start date: December 01, 2014
• End date: November 28, 2015
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Rosimeire Coura Barcelos
• Supervisor: Timothy James Donohoe
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: University of Oxford, England
• Associated to the scholarship: 12/24783-1 - Morita-Baylis-Hillman in medicinal chemistry: synthesis and neuroprotective, antimicrobial and antitumoral biological evaluations of new heterocycles, oximes and nitrones, BP.PD

Abstract

In recent years, there has been an increase in methodology reports aimed to synthesize the 1,2-aminoalcohol core. This key unit is highly sought because of its occurrence in many different organic compounds of value ranging from natural products to pharmaceutical agents. Methods that allow the regioselective and stereospecific addition of nitrogen and oxygen across an alkene are rare, and continue to be influenced by the osmium catalysed aminohydroxylation reaction, discovered by this research area's father, the Nobel Laureate K. B. Sharpless. This proposal is based in amino acids chemistry and the exploration of a fundamentally new route to synthesize peptides by using a hydroxyamination (oxidation) reaction of an alkene. Another objective is to join peptide sequences together by using alkene containing molecules rather than carbonyls as the reacting element, and also to join new peptides to other complex biomolecules, such as sugars, to create hybrids with definable properties. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

COLOMER, IGNACIO; BARCELOS, ROSIMEIRE COURA; CHRISTENSEN, KIRSTEN E.; DONOHOE, TIMOTHY J.. Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation. ORGANIC LETTERS, v. 18, n. 22, p. 5880-5883, NOV 18 2016. (14/16516-9)

COLOMER, IGNACIO; BARCELOS, ROSIMEIRE COURA; DONOHOE, TIMOTHY J.. Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri- and Tetrasubstituted Cyclobutanes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 55, n. 15, p. 4748-4752, APR 4 2016. (14/16516-9)