Some of the SeRMN staff presented our last research work about chirality at The first International Conference on Symmetry, Symmetry 2017, that took place from16th to 18th October in Barcelona. Find below a summary of our contribution.
Míriam Pérez-Trujillo presented a lecture entitled: “Chiral Recognition by Dissolution Dynamic Nuclear Polarization NMR Spectroscopy”
Abstract: The recognition of enantiomeric molecules by chemical analytical techniques is still a challenge. A method based on d-DNP (dissolution dynamic nuclear polarization) NMR spectroscopy to study chiral recognition was described for the first time . DNP allows boosting NMR sensitivity by several orders of magnitude, overcoming one of the main limitations of NMR spectroscopy . A method integrating d-DNP and 13C NMR-aided enantiodifferentiation using chiral solvating agents (CSA) was developed, in which only the chiral analyte was hyperpolarized and selectively observed by NMR. The described method enhances the sensitivity of the conventional NMR-based procedure  and lightens the common problem of signal overlapping between analyte and CSA. As proof on concept, racemic metabolite 13C-labeled DL-methionine was enantiodifferentiated by a single-scan 13C NMR experiment. This method entails a step forward in the chiral recognition of small molecules by NMR spectroscopy; it opens new possibilities in situations where the sensitivity is limited, for example, when low analyte concentration available or when measurement of an insensitive nucleus required. The advantages and current limitations of the method, as well as future perspectives, are discussed.
“Chiral Recognition by Dissolution DNP NMR Spectroscopy of 13C-Labeled DL-Methionine” By Eva Monteagudo, Albert Virgili, Teodor Parella and Míriam Pérez-Trujillo.. Anal. Chem., 2017, 89 (9), pp 4939–4944 DOI: 10.1021/acs.analchem.7b00156
A method based on d-DNP NMR spectroscopy to study chiral recognition is described for the first time. The enantiodifferentiation of a racemic metabolite in a millimolar aqueous solution using a chiral solvating agent was performed. Hyperpolarized 13C-labeled DL-methionine enantiomers were differently observed with a single-scan 13C NMR experiment, while the chiral auxiliary at thermal equilibrium remained unobserved. The method developed entails a step forward in the chiral recognition of small molecules by NMR spectroscopy, opening new possibilities in situations where the sensitivity is limited, for example, when a low concentration of analyte is available or when the measurement of an insensitive nucleus, like 13C, is required. The advantages and current limitations of the method, as well as future perspectives, are discussed.
“Optimized polarization build-up times in dissolution DNP-NMR using a benzyl amino derivative of BDPA” by José Luis. Muñoz Gómez, Eva Monteagudo, Vega LLoveras, Teodor Parella, Jaume Veciana and José Vidal Gancedo. RSC Advances, 2016, 6, 27077. DOI: 10.1039/c6ra00635c
The synthesis of two novel BDPA-like radicals, a benzyl amino (BAm-BDPA, 7) and a cyano (CN-BDPA, 5) derivative, is reported and their behaviour as polarizing agents for fast dissolution Dynamic Nuclear Polarization (DNP) is evaluated. Continue reading Optimized polarization build-up times in dissolution DNP-NMR using a benzyl amino derivative of BDPA
“A Benzyl Alcohol Derivative of BDPA Radical for Fast Dissolution Dynamic Nuclear Polarization NMR Spectroscopy” by José Luis Muñoz Gómez, Eva Monteagudo, Vega Lloveras, Teodor Parella, Jaume Veciana and José Vidal Gancedo. Organic & Biomolecular Chemistry, 2015, 13:2689-2693. DOI: 10.1039/C4OB02356K
The synthesis, structural characterization and the successful application of a carbon centered radical derived from 1,3-bisdiphenylene-2-phenylallyl (BDPA), its benzyl alcohol derivative (BA-BDPA), as a polarizing agent for Dynamic Nuclear Polarization (DNP) are described. Continue reading A New Polarizing Agent for Dissolution-DNP
“Real-time assessment of 13C metabolism reveals an early lactate increase in the brain of rats with acute liver failure” by Laia Chavarria, Jordi Romero-Giménez, Eva Monteagudo, Silvia Lope-Piedrafita, Juan Cordoba. NMR in Biomedicine (2014) 28:17-23. DOI: 10.1002/nbm.3226
Intracranial hypertension is a severe complication of acute liver failure (ALF) secondary to brain edema. The pathogenesis of cerebral edema in ALF is not clear, but seems to be related to energy metabolism in which lactate may have an important role. The aim of this study was to follow the synthesis of brain lactate using a novel in vivo metabolic technology in a rat model of ALF. Continue reading Hyperpolarized 13C Magnetic Resonance in Acute Liver Failure Rats
Next week several SeRMN members will present our research work at the Joint Annual meeting ISMRM-ESMRMB 2014 that will take place in Milan (Italy) from 10th to 16th May. Find below a summary of our contributions.
Continue reading Presentations at the Joint Annual Meeting ISMRM-ESMRMB 2014
Find below an abstract of SeRMN contribution at 4th International DNP Symposium that will be held August 28-31, 2013, in Copenhagen (Denmak).
Enantiodiscrimination Studies by 13C DNP-NMR Spectroscopy
The determination of enantiomeric purity of drugs and/or endogenous molecules is crucial since its chirality could determine its pharmacological or biological behavior . Many analytical techniques are available to determine the enantiomeric excess (ee) such as, circular dichroism, capillary electrophoresis, chromatographic techniques with chiral stationary phases, etc.; having each of them drawbacks and advantages . Nuclear magnetic resonance (NMR) using a chiral solvating agent (CSA) as chiral auxiliary is an easy, fast and very powerful analytical tool that allows the measurement of ee by simple signal integration . Continue reading Poster presentation at 4th International DNP Symposium
- Date: Thursday 27th June, 2013
- Hour: 3 pm
- Location: SeRMN, Facultats de Ciències i Biociències, C2/-135
- Speaker: Eva Monteagudo, technician at SeRMN, UAB
Continue reading Enantiodiscrimination Studies by 13C DNP-NMR Spectroscopy
Dynamic Nuclear Polarization is the method for obtaining strongly polarised nuclear spins, resulting in enhanced NMR signals for 13C and 15N nuclei in solution-state
Our NMR facility (SeRMN) has recently installed a HyperSense® (Oxford Instruments), a new instrument capable of delivering a huge sensitivity enhancement for your in-vitro and in-vivo applications allowing an easy and quick switching between both applications.
Liquid-state NMR spectroscopy is an important technique into a wide range of applications. However, it is limited by an intrinsically lack of sensitivity due to the low gyromagnetic ratio and natural abundance of the nuclei usually under study (13C, 15N, etc.) as compared with other analytical methods. Continue reading What is DNP? Obtaining enhanced NMR signals for in-vitro and in-vivo applications
Magnetic resonance spectroscopic imaging (MRSI) of hyperpolarized [1-13C]pyruvate is a promising technique to noninvasively monitor metabolic changes in vivo. This method uses dynamic nuclear polarization (DNP) techniques to obtain tens of thousands fold enhancement in the polarization of [1-13C]pyruvate and its metabolic products, like lactate, providing sufficient MR signal for high spatial and temporal resolution spectroscopic imaging of these metabolites. Continue reading Hyperpolarized 13C magnetic resonance metabolic imaging in a mouse brain glioma model