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Identifier |
000395116 |
Title |
Χημειοενζυμική σύνθεση οπτικώς καθαρών φυσικών προϊόντων και χειρομορφών ενδιάμεσων |
Alternative Title |
Chemoenzymatic synthesis of optically pure natural products and chiral intermediates |
Author
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Μπαριωτάκη, Άννα
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Thesis advisor
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Σμόνου, Ιουλία
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Reviewer
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Στρατάκης, Μανώλης
Ξενάκης, Αριστοτέλης
Κατερινόπουλος, Χαράλαμπος Ε.
Βασιλικογιαννάκης, Γεώργιος Ε.
Μπουριώτης, Βασίλης
Βελώνια, Κέλλυ
|
Abstract |
In the present thesis the stereoselective enzymatic reductions with NADPHdependent
ketoreductases for the synthesis of important chiral intermediates were
studied and more specifically for the synthesis of optically pure hydroxy-keto
esters,1,3-dihydroxy esters and α- or γ-substituted hydroxy-keto esters. Also, a
chemoenzymatic approach for the synthesis of the natural product (R)-
Goniothalamin has been accomplished. All products derived from enzymatic
reductions were analyzed and characterized and their absolute configuration was
determined by NMR spectroscopy. These research projects were accomplished
under the Research Program HRAKLEITOS II.
In the first part, the enzymatic reduction of tert-butyl 3,5-dioxo-hexanoate
for the synthesis of 3,5-dihydroxy esterswas completed, in a two-step, one-pot
method in the same reaction vessel, without the isolation of the intermediate.
These products were synthesized with excellent optical purity and chemical yield.
Ketoreductases proved to be excellent catalysts with high stereoselectivity and
chemoselectivity.
The next part included the studies for the enzymatic reduction of tert-butyl-
2-methyl-3,5-dioxo-hexanoate for the synthesis of 2-methyl-5-hydroxy-3-keto
esters. The products were formed in excellent optical and chemical purity with high
enantiomeric and diastereomeric excess.
Also, the enzymatic reduction of tert-butyl-4-methyl-3,5-dixo-haxanoate was
studied for the synthesis of 4-methyl-5-hydroxy-3-keto esters and 4-methyl-3-
hydroxy-5-keto esters with high stereoselectivity and high enantiomeric and
diastereomeric excesses.
In the next part the chemoenzymatic approach for the synthesis of the
natural product (R)-Goniothalamin, an anti-proliferative agent is presented.
In the last part the investigation of a new photocatalyst of graphitic Carbon
Nitride, for the oxidation of cyclohexanol to cyclohexanone, is described.
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Language |
Greek |
Subject |
Biocatalysis |
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Enzymatic oxidation |
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Enzymatic reduction |
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Graphitic Carbon Nitride |
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Ketoreductases |
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NADPH |
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Oxidoreductases |
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Βιοκατάλυση |
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Ενζυμική αναγωγή |
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Ενζυμική οξείδωση |
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Κετορεδουκτάσες |
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Κυκλοεξανόνη |
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Οξειδορεδουκτάσες |
Issue date |
2015-07-13 |
Collection
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School/Department--School of Sciences and Engineering--Department of Chemistry--Doctoral theses
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Type of Work--Doctoral theses
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Permanent Link |
https://elocus.lib.uoc.gr//dlib/e/d/b/metadata-dlib-1436346647-312304-4578.tkl
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Views |
567 |