Physical Organic Chemistry

NMR MS IMG_0840
IMG_0839 IMG_2064

All organic compounds contain carbon and hydrogen atoms, though their chemical diversity is mind breaking. For example, the number of theoretically plausible organic compounds formed by a total of 17 carbon, nitrogen, oxygen, sulfur and halogen atoms is more than 100 billion1. The large diversity is possible because the individual atoms can be connected in many ways to form molecules with different structures. Molecular structure is what determines the compound’s chemical and physical properties, therefore knowledge of a molecule’s structure is of fundamental importance. Physical organic chemistry uses physical methods to study the structure of organic molecules as well as the interrelationships between molecular structure and chemical, physical and biological properties of organic compounds.

The Laboratory of Physical Organic Chemistry at IOS features state-of-the-art equipment and high level expertise in nuclear magnetic resonance (NMR), X-ray diffraction, masspectrometry, electrochemistry, electron paramagnetic resonance (EPR), surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) to perform studies of the molecular structure and its relationships to chemical reactivity, (bio)physical properties and biological activity of organic compounds. Research activities in many diverse fields are mainly aimed at facilitating drug discovery efforts in the institute and include structural studies of small molecules by NMR, masspectrometry and X-ray diffraction, structural studies of biological macromolecules (proteins and DNA) by NMR, protein-small molecule binding studies by NMR, SPR and ITC, pharmacokinetic and metabolic studies by masspectrometry, mechanistic studies of redox reactions and electrochemical synthesis as well as studies of free radicals in animal tissues by EPR etc.

Selected references:

NMR spectroscopy
Petrova M., Muhamadejev R., Vigante B., Cekavicus B., Plotniece A., Duburs G. and Liepinsh E. Intramolecular C-H•••O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives. Molecules (2011) 16: 8041-8052. DOI
Jaudzems K., Jia X., Yagi H., Zhulenkovs D., Graham B., Otting G., Liepinsh E. Structural basis for 5′-end-specific recognition of single-stranded DNA by the R3H domain from human Sμbp-2. J. Mol. Biol. (2012) 424: 42-53. DOI

Read more on NMR group’s webpage

X-ray diffraction
Anatoly Mishnev and Glebs Kiselovs. New Crystalline Forms of Piroxicam. Z. Naturforsch. (2013), 68b, 168–174. DOI
Sarcevica I., Orola L., Veidis M.V., Podjava A., Belyakov S. Crystal and Molecular Structure and Stability of Isoniazid Cocrystals with Selected Carboxylic Acids. Crystal Growth and Design (2013), 13: 1082-1090. DOI

Masspectrometry
Grinberga, S., Dambrova, M., Latkovskis, G., Strele, I., Konrade, I., Hartmane, D., Sevostjanovs, E., Liepinsh, E., Pugovics, O. Determination of trimethylamine-N-oxide in combination with l-carnitine and γ-butyrobetaine in human plasma by UPLC/MS/MS. Biomed. Chromatogr. (2015), 29: 1670–1674.

EPR
Baumane L.; Krauze A.; Krasnova L.; Beļakovs S.; Dubur G.; Stradins J. Role of Steric Factors in Intramolecular H-bond Formation and Peculiarities of Electrochemical Oxidation of Ethyl 6-Alkylsulfanyl-5-Cyano-2-Methyl-4-Phenyl-1,4-Dihydropyridine-3-Carboxylates. Chem. Heterocycl. Comp. (Engl. Ed.) (2014), 49: 1623-1630.
Petukhov V.I.; Baumane L.H.; Dmitriev E.V.; Vanin A.F. Quantitative Shifts of Electrogenic Metals in Epidermal Cells in the Setting of Oxidative/Nitrosative Stress – What Could They Stand For? JSM Biotechnol. Bioorg. (2014), 2: 1045.
Zarins A.; Kizane G.; Supe A.; Knitter R.; Tiliks Jr. J.; Baumane L. Influence of chemisorption products of carbon dioxide and water vapour on radiolysis of tritium breeder. Fusion Eng. Des. (2014), 89: 1426-1430.

Electrochemistry
Malina I.; Kampars V.; Turovska B. Synthesis, optical and electrochemical properties of substituted 2-cinnamoyl-1, 3-indandione O-methyl ethers.  J. Mol. Struct. (2016), 1115: 241-249.
Batenko N.; Belyakov S.; Turovska B.; Valters R. A novel method for the synthesis of benzimidazole-based 1,4-quinone derivatives. Tetrahedron Lett. (2016),57: 292-295.
Turovska B.; Lund H.; Lūsis V.; Lielpētere A.; Liepinš E.; Beljakovs S.; Goba I.; Stradiņš J. Photoinduced 1,2,3,4-tetrahydropyridine ring conversions. Beilstein J. Org. Chem (2015), 11: 2166-2170.