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Selection of conditions for attaining choosen nucleoaminoacid

Tomasz Ryszard Mazurek

Abstract

Introduction The purpose of my study was to investigate the possibility of adapting the alkylation reaction described in the literature[1] for the synthesis of (S)-tert-butyl [1-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-phenylethyl]carbamate as a potential precursor of willardiine. Results and discussion I started by examining the possibility of alkylation of thymine 25, based on the procedure found in the literature [1]. After obtaining promising results I began to investigate the alkylation reaction of uracil 1, first with a derivative of O-mesylo-L-serine 24, but the results were not satisfactory. I moved to a series of reactions with iodide 2 as alkylating agent for uracil 1. The obtained performance was satisfactory (55% and 57%). During my studies I discovered that the enantiomeric excess of 3 amino acid changes with time of the reaction. After further studies I noted a significant decrease in the angle of specific rotation, and its complete decay after 26 days of the reaction. I have proposed a new mechanism of reaction, taking into account the possibility of alkylation of the uracil 1 by alkene 20 which is created from a retro-Michael reaction of the primary reaction product, the amino acid 3. Summary My research has led to the development of new method of synthesis and (S)-tert-butyl [1-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-phenylethyl]carbamate which is a precursor for the synthesis of willardiine. The crucial point seems to be the time of alkylation reaction, which significantly affects the enantiomeric excess in the final product. In addition, a change in the mechanism of the reaction with time is not completely clear and requires further studies.
Diploma type
Engineer's / Bachelor of Science
Diploma type
Engineer's thesis
Author
Tomasz Ryszard Mazurek (FC) Tomasz Ryszard Mazurek,, Faculty of Chemistry (FC)
Title in Polish
Dobór warunków otrzymywania wybranego nukleoaminokwasu
Supervisor
Mariola Koszytkowska-Stawińska (FC/DOC) Mariola Koszytkowska-Stawińska,, Department Of Organic Chemistry (FC/DOC)Faculty of Chemistry (FC)
Certifying unit
Faculty of Chemistry (FC)
Affiliation unit
Department Of Organic Chemistry (FC/DOC)
Study subject / specialization
, Biotechnologia
Language
(pl) Polish
Status
Finished
Defense Date
09-02-2016
Issue date (year)
2016
Reviewers
Zbigniew Ochal (FC/CDSB) Zbigniew Ochal,, Chair of Drug and Cosmetics Biotechnology (FC/CDSB)Faculty of Chemistry (FC) Mariola Koszytkowska-Stawińska (FC/DOC) Mariola Koszytkowska-Stawińska,, Department Of Organic Chemistry (FC/DOC)Faculty of Chemistry (FC)
Keywords in Polish
willardiina, uracyl, reakcja alkilowania
Keywords in English
willardiine, uracil, alkilation reaction
Abstract in Polish
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Uniform Resource Identifier
urn:pw-repo:WUT1c7f042869ad44a1950f1bbeb2a998ce