Author, Institution: Gita Kasparavičienė, Kaunas University of Technology
Science area, field of science: Natural Sciences, Chemistry, N003
Scientific Supervisors: Prof. Dr. Hab. Algirdas Šačkus (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Assoc. Prof. Dr. Neringa Kleizienė (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Dissertation Defense Board of Chemistry Science Field:
Prof. Dr. Vytautas Getautis (Kaunas University of Technology, Natural Sciences, Chemistry, N003) – chairperson
Chief Researcher Dr. Linas Labanauskas (State Research Institute Center for Physical Sciences and Technology, Natural Sciences, Chemistry, N003)
Prof. Dr. Hab. Vytautas Mickevičius (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Assoc. Prof. Dr. Jolanta Rousseau (Artois University, France, Technological Sciences, Chemical Engineering, T005)
Dr. Ingrida Tumosienė (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Dissertation defense meeting will be at Rectorate Hall of Kaunas University of Technology (K. Donelaičio 73-402, Kaunas)
The doctoral dissertation is available at the library of Kaunas University of Technology (Gedimino 50, Kaunas) and on the internet: G. Kasparavičienė el. dissertation (PDF)
Annotation: Stereoselective and regioselective synthesis of novel heterocyclic amino acids in their N-Boc and O-Me protected forms has been developed from commercially available chiral or achiral carboxylic acids. New 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates have been synthesized from piperidine-4-carboxylic acid via β-ketoester which was converted into β-enamino ketone and coupled with aryl and alkyl hydrazines. Cyclocondensation of β-enamino ketones from piperidine-4-carboxylic, enantiomerically pure (R)- and (S)-piperidine-2-carboxylic, and (R)- and (S)-pyrrolidine-2-carboxylic acids with 55% hydrazine hydrate solution followed by N-alkylation with alkyl iodides afforded a library of chiral and achiral 3-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates and 3-(N-Boc-pyrrolidin-2-yl)-1H-pyrazole-4-carboxylates. New highly stereopure enantiomeric and diastereomeric methyl 2-[(Boc-amino)cycloamin-1-yl]alkanoates have been synthesized from enantiopure α-monosubstituted 2-hydroxyalkanoic acids via a three-step synthetic approach. The nucleophilic substitution of the chiral and achiral azaheterocyclic amines and the corresponding chiral triflate esters is followed by the inversion of reacting C-2 of triflate esters. The subsequent modification of synthesized methyl 2-[(Boc-amino)cycloamin-1-yl]alkanoates has led to new chiral N-Boc- and N-nosyl-dipeptides with a fragment of L-phenylalanine. In general, these new synthetic azaheterocyclic amino acids are excellent building blocks for peptide synthesis and wider synthetic manipulations for pharmaceutical use.
June 18 d. 11:00
Rectorate Hall at Kaunas University of Technology (K. Donelaičio 73-402, Kaunas)
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