Pedro M. P. Gois
University of Lisbon
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Featured researches published by Pedro M. P. Gois.
Chemical Reviews | 2009
Nuno R. Candeias; Luís C. Branco; Pedro M. P. Gois; Carlos A. M. Afonso; Alexandre Trindade
Centro de Quı́mica-Fı́sica Molecular (CQFM) and Institute of Nanosciences and Nanotechnology (IN), Departamento de Engenharia Quı́mica e Biológica, Instituto Superior Técnico, 1049-001 Lisboa, Portugal, REQUIMTE, Departamento de Quı́mica, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal, and iMed.UL, Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal
Journal of the American Chemical Society | 2012
Pedro M. S. D. Cal; João B. Vicente; Elisabete Pires; Ana V. Coelho; Luis F. Veiros; Carlos Cordeiro; Pedro M. P. Gois
Protein modification has entered the limelight of chemical and biological sciences, since, by appending small molecules into proteins surfaces, fundamental biological and biophysical processes may be studied and even modulated in a physiological context. Herein we present a new strategy to modify the lysines ε-amino group and the proteins N-terminal, based on the formation of stable iminoboronates in aqueous media. This functionality enables the stable and complete modification of these amine groups, which can be reversible upon the addition of fructose, dopamine, or glutathione. A detailed DFT study is also presented to rationalize the observed stability toward hydrolysis of the iminoboronate constructs.
Chemical Communications | 2006
Luís C. Branco; Pedro M. P. Gois; Nuno M. T. Lourenço; Vanya B. Kurteva; Carlos A. M. Afonso
New chiral ionic liquids can be prepared simply by combining the tetra-n-hexyl-dimethylguanidinium cation with readily available chiral anions and used as an asymmetric inducing agent as demonstrated for catalytic Rh(II) carbenoid C-H insertion and Sharpless dihydroxylation.
Organic Letters | 2010
João N. Rosa; R. Sudarshan Reddy; Nuno R. Candeias; Pedro M. S. D. Cal; Pedro M. P. Gois
NHC-iron complexes prepared in situ very efficiently afforded benzoates via the aerobic oxidative aromatic esterification of aldehydes with boronic acids. This method uses equimolar amounts of both the aldehyde and the boronic acid allowing the preparation of benzoates in yields up to 97%.
Journal of Organic Chemistry | 2008
Alexandre Trindade; Pedro M. P. Gois; Luis F. Veiros; Vânia André; M. Teresa Duarte; Carlos A. M. Afonso; Stephen Caddick; F. Geoffrey N. Cloke
An efficient new methodology for the arylation of aldehydes is disclosed which uses dirhodium(II) catalysts and N-heterocyclic carbene (NHC) ligands. Complexes of Rh 2(OAc) 4 with one and two NHCs attached on the axial positions were successfully isolated, fully characterized, and used as catalysts in the reaction. The saturated monocomplex ((NHC 5)Rh 2(OAc) 4) 31 was shown to be the most active catalyst and was particularly efficient in the arylation of alkyl aldehydes. DFT calculations support participation of complexes with one axial NHC in the reaction as the catalysts active species and indicate that hydrogen bonds involving dirhodium unit, reactants, and solvent (alcohol) play an important role on the reaction mechanism.
Chemical Reviews | 2016
Nuno R. Candeias; Roberta Paterna; Pedro M. P. Gois
This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts. Reactions with diazoalkanes, aryldiazomethanes, trimethylsilyldiazomethane, α-diazo esters, and disubstituted diazo compounds are covered, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters. The recent reports on the enantioselective version of ketone homologation reactions are gathered in one section, followed by reports on the use of cyclic ketones ring expansion in total synthesis. Although the first reports of this reaction appeared in the literature almost one century ago, the recent achievements, in particular, for the asymmetric version, forecast the development of new breakthroughs in the synthetically valuable field of diazo chemistry.
Angewandte Chemie | 2014
Pedro M. S. D. Cal; Gonçalo J. L. Bernardes; Pedro M. P. Gois
Moving tracks from maleimide: New site-selective protein modification reactions at cysteine have been developed. Unlike conventional maleimide conjugation, which results in a labile thioether succinimide, the new bioconjugation reactions result in stable conjugates and provide opportunities to develop a new generation of homogeneous, stable, and therapeutically useful conjugates.
Chemical Communications | 2007
Carlos A. M. Afonso; Luís C. Branco; Nuno R. Candeias; Pedro M. P. Gois; Nuno M. T. Lourenço; Nuno M. M. Mateus; João N. Rosa
This feature article is a description of the achievements made on the development of attractive sustainable approaches to synthetic organic chemistry, namely, catalyst reuse by simple dissolution in water and ionic liquids and asymmetric transformations induced by readily available chiral ionic liquids.
Chemical Communications | 2005
Nuno R. Candeias; Pedro M. P. Gois; Carlos A. M. Afonso
Water is an efficient solvent for the Rh2(OAc)4 catalysed intramolecular C-H insertion of a range of diazo substrates without competitive water insertion. Due to the high solubility and stability of the catalyst in water, the catalyst can be efficiently reused.
Tetrahedron Letters | 2003
Pedro M. P. Gois; Carlos A. M. Afonso
Abstract α-Phosphono-lactams were obtained, with high regio and stereoselectivities via Rh 2 (OAc) 4 -catalysed intramolecular CH insertion in an ionic liquid. This system proved to be highly efficient over 5–6 cycles.