Bioorganic Chemistry Research Group
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Welcome to the Bioorganic Chemistry Research Group

The Bioorganic Chemistry group focus its activity on pursuing new insights in to our understanding of health related biological processes. With a wide experience on asymmetric organic synthesis the group is interested in the design and synthesis of small molecules for therapeutic application or their use in the elucidation of biological function. By combining a series of multidisciplin ary tools and techniques including in-house developed synthetic methodologies, computer-based molecular modelling (QM calculations, docking and Molecular Dynamics) and advanced spectroscopic techniques (i.e. STD-NMR), the main activity of the group concerns identification of small molecules as key modulators and/or inhibitors of target enzymes associated to specific biological functions. This approach provides target validation as well as starting points for further drug discovery.
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Pre-Doctoral Grant available.  
   
Ph.D. Thesis on glycomimetics en route to glycosyltransferases inhibitors
May 3, 2017
Mattia Ghirardello
Revealing the Essence of Chemical Reactivity by Addiing a Topological Perspective
Conferencia. P. Merino
Università di Pavia. Italia. 16/03/17
Cover Picture (Hot paper)
in Chem. Eur. J.
Congratulations Vero!
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Cover Picture (Editor`s choice) in
Chem. Biol. Drug Design
Congratulations Eduardo!
Posted February 10, 2017  
Our group has been awarded with a FPI pre-doctoral grant for carrying out Ph.D. studies in our laboratories on synthesis of inhibitors (glycomimetics) targeting glycosyltransferasas. The call will be published in the next call of FPI grants. If you are interested in joining us write to e-mail indicated under "Contact" or contact directly Prof. Pedro Merino or Prof. Tomas Tejero.  
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Organocatalytic Oxa-Michael Reactions  
Posted February 10, 2017  
A collaboration with Prof. Vicario's research group at the University of Basque Country (Bilbao, Spain) showed that 2-hydroxydihydropyran-5-ones behave as excellent polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic compounds are used as unconventional O-pronucleophiles in the initial oxa-Michael reaction, also leading to the formation of a single stereoisomer under a dynamic kinetic resolution (DKR) process.A complete experimental and computational study confirmed the initially proposed DKR process during the catalytic oxa-Michael/Michael cascade reaction and also explained the kinetic/thermodynamic pathway operating in each cases.   
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Invited Review on Inhibitors of Isoprenoid Synthesis  
Posted February 10, 2017  
A revision summarizing the approaches currently employed to synthesize new inhibitors of isoprenoid biosynthesis. Bisphosphonates are mainly prepared through reaction of carboxylic acids with phosphorus reagents, Michael addition to tetraethylvinylidenebisphosphonate and alkylation of tetralkylmethyl bisphosphonate. Approaches to non-bisphosphonate derivatives include a variety of methodologies depending on the structure of the target compound. Post-translational lipid modifications farnesylation and geranylgeranylation of proteins (protein prenylation) have been identified to mediate critical events in cancer, cardiovascular disorders, malaria and bone disorders like osteoporosis. To date eight compounds are commercialized for the treatment of bone disorders, and there are considerable efforts to develop selective small molecules that inhibit protein prenylation.  
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Highly Enantioselective Organocatalytic Reactions with Nitrone Ylides.  
Posted February 10, 2017  
A new publication from Vero's Ph.D. Thesis. Congratulations Vero!. The work made in collaboration with Prof. Vicario's research group at the University of Basque Country (Bilbao, Spain) established that reaction of nitrones with enals under iminium activation can be modulated by using cooperative H-bonding catalysis to induce the participation of a nitrone ylide (C-N-C) instead of the classical C-N-O dipole  
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Evidences of Carbocation Intermediates in Thionation of Alcohols  
Posted February 10, 2017  
Evidences that carbocations are involved in the mechanism of the thionation of alcohols with Lawesson's reagent have been found. The mechanism is completely different to that recently established for thionation of carbonyls. The presence of a phenyl ring at the alcoholic carbon exerts a pivotal role in the stability of the carbocation, enabling an S-π interaction which is crucial for favoring thionation instead undesired elimination. The study is in a complete agreement with the different behavior observed experimentally for primary, secondary and tertiary alcohols (bearing a phenyl ring or not) and predict the best conditions for minimizing undesired elimination.  
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Amino Acid-Nucleoside Conjugates.  
Posted November 2, 2016  
A new publication from Mattia's Ph.D. Thesis. Congratulations Mattia!. Representative derivatives of uridine-conjugate amino acids suitable protected for Fmoc solid-phase chemistry, have been prepared through efficient protocols using "click" reactions that include thio-ene radical reaction, copper-catalyzed azide alkyne cycloaddition (CuAAC) and a Staudinger-Vilarrasa reaction  
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Research Project from MINECO, Spain  
Posted September 27, 2016  
Our group has been awarded with a National Project for the next three years on the topic: Rational Design of Glycomimetics Inhibitors of Glycosyltransferases. CTQ2016-76155-R.
The project includes a pre-doctoral FPI grant
 
   
Ph.D. Thesis  
Posted September 7, 2016  
David Roca won his Ph.D. title (Estudio computacional de reacciones con nitronas que no son lo que parecen) last September 6. The commission formed by Prof. Jose M. Saa (president), Prof. Luis R. Domingo and Dr. Julia Contreras gave him the maximum vote: Sobresaliente cum laude
The Ph.D. Thesis has been awarded with the Prize to Excelence of Young Researchers given by the StFrancis-Prof. Thyagarajan Foundation (San Antonio, TX, USA)
 
   
Mechanism of Lawesson's thionation of carbonyl compounds  
Posted July 27, 2016  
The mechanism of Lawesson's thionation resembles the Wittig reaction and takes place in two steps without formation of any zwitterionic intermediate. Both steps are concerted, the second one being the rate-limiting step. Notably, an encounter pair is formed between the reagents before starting the reaction  
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Autocatalytic Processes with Nitrone Ylides  
Posted July 15, 2016  
A catalytic amount of n-BuLi is enough for launching a catalytic cycle in which a nitrone ylide reacts with an aldehyde to produce 3-oxazolines and a water molecule which is reutilized for regenerating the catalytic species. Water is autocatalytic and promotes loss of the next water molecule  
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This publication has been chosen to be highlighted on the ChemistryViews website  
   
The Role of Pyrophosphate in Glycosltransferases  
Posted June 12, 2016  
Computational and Structural studies with GalNAc-T2 provide further insights into the catalytic cycle mechanism of this family of enzymes and corroborate the requirement of beta-phosphate for binding.  
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Glycomimetics Targeting Transglycosylases  
Posted April 2, 2016  
A a minimum of three glucose units linked via a beta-(1,3) linkage are required for achieving molecular recognition at the binding donor site of transglycosylase ScGas2 a suitable model for designing new therapeutic agents against Aspergillus fumigatus  
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Revealing Stepwise Mechanisms in Dipolar Cycloadditions  
Posted February 2, 2016  
A DFT study of the reaction between nitrones and isocyanates revealed that the cycloaddition reaction takes place through a concerted mechanism in gas phase and in apolar solvents  but a stepwise mechanism in  polar solvents.  
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