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Stereoselective Organic Synthesis Group

The Stereoselective Organic Synthesis Group has its origin in 1992, and is currently formed by 5 senior researchers and several PhD and undergraduate students. The main topic research is the synthesis, the conformational analysis and the study of the biological activity of natural and new glycopeptides. Our research is also focused on the synthesis of new compounds by stereoselective organic processes. As an applied research line, we are interested in the use of nuclear magnetic resonance to study different processes in wine and bacterial cultures.

Research lines

Synthesis, conformational analysis and activity of glycopeptides (+)

Synthesis, conformational analysis and activity of glycopeptides

In recent years, much attention has been paid to the design of novel molecules with improved biological properties with respect to the natural ones. In this regard, the synthesis of conformationally restricted amino acids and their further incorporation into a peptide or glycopeptide is an effective tool to obtain molecules that display a priori the required bioactive conformation. Based on this idea, we are carrying out a multidisciplinary research, which includes organic synthesis, molecular biology, state-of-the-art NMR experiments and molecular modeling. A set of building blocks synthesized in our group are used as starting material for the rational design of novel and structurally modified N-, S- and O-glycopeptides that mimic the natural ones. In the case of O-glycopeptides, we focused on the partially glycosylated mucins, since these antigens can be regarded as promising candidates for the development of cancer vaccines. In the case of S-glycosylation, we studied the corresponding glycopeptide derivatives from the point of view of their emergence in the field of bacteriocins. The N-glycosylation was used to design N-glycopeptides with complete defined structure with the help of CH-π interactions as the key stabilizing factors. Our first research work involved the synthesis of simplest model beta-O-glucosylated peptides derived from Ser and Thr and their conformational analysis. Following a protocol based on the use of NMR and molecular dynamics (MD), we could conclude that the beta-O-glucosylation of these model glycopeptides significantly affect the conformation of the peptidic moiety.

Stereoselective Organic Synthesis (+)

Stereoselective Organic Synthesis

The principal strategies of new stereoselective processes used by our research group are oriented to gain conformationally restricted glycopeptides or glycoproteins, which involve the replacement of some of the natural amino acids of the backbone by non-natural ones with a similar structure but presenting certain conformational rigidity. Our group has a wide experience in the synthesis of this kind of modified amino acids using well-defined synthetic methodologies developed in the last years

Applied Nuclear Magnetic Resonance (+)

Applied Nuclear Magnetic Resonance

Nuclear magnetic resonance (NMR) spectroscopy is a powerful analytical technique and has an outstanding position in the field of complex chemical analysis of agricultural and food products as a potent analytical procedure for chemical characterization. As an important beverage, wine consists of several hundred components, and these are present at different concentrations, with the major components being water, ethanol, glycerol, sugars and organic acids. The NMR spectroscopy of wine has proven to be useful for assessing wine quality, for example, in the verification of wine origin, age, and the effects of adulteration through the SNIF-NMR method.

In recent years, the use of high-resolution NMR techniques in the study of wine has attracted the interest of several groups. In our research project related to the use of NMR spectroscopy as a useful tool in wine chemistry, we have focused on the study of the the time course of the evolution of several compounds in the alcoholic and malolactic fermentation of grape must by quantitative 1H NMR spectroscopy using water suppression and an external standard.

By other side, NMR could be used as a rapid and efficient method for assessing antimicrobial drug susceptibility. NMR spectroscopy is potentially valuable in determining the metabolic composition of yeast suspensions incubated with a drug. In addition, it is a high performance automated method with low operating costs, so that operator time and reagent cost are both greatly reduced. These studies are developed with the Infectious diseases Group (Dr. José Antonio Oteo) from CIBIR

Group research

Latest publications

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Detection of Tumor-Associated Glycopeptides by Lectins: The Peptide Context Modulates Carbohydrate Recognition

D. Madariaga, N. Martínez-Sáez, V.J. Somovilla, H. Coelho, J. Valero-González, J. Castro-López, J.L. Asensio, J. Jiménez-Barbero, J.H. Busto, A. Avenoza, et al
ACS Chemical Biology, 2015

Conformational analysis of peptides and glycopeptides derived from the consensus sequence for β-O-glucosylation

V.J. Somovilla, N. Martínez-Sáez, A. Fernández-Tejada, B.G. de la Torre, D. Andreu, J. Jiménez-Barbero, J.L. Asensio, A. Avenoza, J.H. Busto, F. Corzana J.M. Peregrina
Current Topics in Medicinal Chemistry, 2015

I + D Projects

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Latest congress communications

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Latest invited conferences

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PhD thesis works

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Síntesis y Reactividad en Procesos de Metátesis de Sistemas Azabiciclo[2.2.n] Sustituidos en Posición Cabeza de Puente

Author: Javier Carreras Pérez-Aradros
Director: Alberto Avenoza Aznar y Jesús H. Busto Sancirián
Date: 05/02/2010
Universidad de La Rioja

Beta-O-Glicosilación de péptidos que incorporan aminoácidos no naturales

Author: Alberto Fernández Tejada
Director: Jesús Manuel Peregrina García y Francisco Corzana López
Date: 16/07/2009
Universidad de La Rioja

Master thesis works

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Cicloadición [2+2] formal entre alquenos derivados de carbohidratos y acrilatos.

Author: Iván García González
Director: Alberto Avenoza Aznar; J. Héctor Busto Sancirián
Course: 2010/11
Universidad de La Rioja

Estudios sobre el epítopo Gly-Ser-Thr-Ala del glicopéptido mucina MUC-1

Author: David Madariaga Merino
Director: Alberto Avenoza Aznar; J. Héctor Busto Sancirián
Course: 2010/11
Universidad de La Rioja

Resonancia magnética nuclear como técnica alternativa en estudios de susceptibilidad antimicrobianos

Author: Lara García Álvarez
Director: Jesús M. Peregrina García; José A. Oteo Revuelta; J. Héctor Busto Sancirián
Course: 2009/10
Universidad de La Rioja

Metátesis de reorganización de anillo (RRM) sobre el sistema 7-azabiciclo [2.2.1] hept-2-eno-1-carboxilato de metilo, sustituido en la posición cabeza de puente.

Author: Victor Rojas Ocariz
Director: Alberto Avenoza Aznar; J. Héctor Busto Sancirián
Course: 2009/10
Universidad de La Rioja

Participation in other master programs

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National and international relations

Cativiela Marín, Carlos. Facultad de Ciencias. departamento de Química Orgánica. Universidad de Zaragoza. España
Jiménez Barbero, Jesús. Centro de Investigaciones Biológicas, CSIC. España
García Laureiro, José Ignacio. Instituto de Ciencias de los Materiales de Aragón, CSIC. Zaragoza. España
Asensio, Juan Luís. Instituto de Química Orgánica, CSIC. España
Balling Engelsen, Soren. Centre for Advanced Food Studies (LMC), The Royal Veterinary and Agricultural University (KVL). Dinamarca