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Identifier 000413027
Title α) Στερεοεκλεκτικές βιοαναγωγές α-αμιδο-β-κετο εστέρων β) Στερεοεκλεκτική σύνθεση οπτικά ενεργών γ-βουτυρολακτονών μέσω ενζυμικών αναγωγών 2-μονο- και 2,2-δι-υποκατεστημένων 1,3-δικετονών
Alternative Title a) Stereoselective bioreduction of α-amido-β-keto esters b) Stereoselective synthesis of optically pure β,γ-disubstituted and trisubstituted γ-butyrolactones via enzymatic reduction of 2-substituted and 2,2-disubstituted 1,3-diketones
Author Γιαννόπουλος, Βασίλειος Π.
Thesis advisor Σμόνου, Ιουλία
Reviewer Στρατάκης, Εμμανουήλ
Βασιλικογιαννάκης, Γεώργιος
Abstract The subject of the present thesis is the study of stereoselective enzymatic reductions with ketoreductases for the preparation of compounds, which are useful chiral intermediates-building blocks for the synthesis of high added value natural products. In the first part, the stereoselective bioreduction of α-amido-β-keto esters using various isolated ketoreductases for the synthesis of optically pure β-hydroxy-α-amido esters is presented. In particular, the stereoselective synthesis of the β-hydroxy-α-amido esters, which are derivatives of allo-threonine and β-hydroxy leucine, using NADPH-dependent ketoreductases was achieved with excellent reaction rates and excellent diastereoselectivity. In the case of the β-hydroxy-α-amido ester, which is derivative of allo-threonine, the appropriate ketoreductase, which led to the synthesis of anti-tert-butyl 2-acetamido-3-hydroxybutanoate in high enantioselectivity, was also determined. In the second part, the stereoselective synthesis of optically pure β,γ-disubstituted and trisubstituted γ-butyrolactones via enzymatic reduction of 2-substituted and 2,2-disubstituted 1,3-diketones using ketoreductases is described and has resulted in the synthesis of three different γ-butyrolactones in high chemical yields, high diastereoselectivity and in some cases with good enantioselectivity. One remarkable result is that, one of the three γ-butyrolactones was synthesized successfully in a one-pot process without isolation of the intermediate products and using only one enzyme.
Language Greek
Subject Chiral intermediates
Ketoreductases
Stereoselective bioreduction
Κετορεδουκτάσες
Στερεοεκλεκτική βιοαναγωγή
Χειρόμορφα ενδίαμεσα
β-hydroxy-α-amido esters
β-υδρόξυ-α-αμιδο εστέρες
γ-butyrolactones
γ-βουτυρολακτόνες
Issue date 2017-11-23
Collection   Faculty/Department--Faculty of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
Permanent Link https://elocus.lib.uoc.gr//dlib/c/2/a/metadata-dlib-1512557550-458716-16842.tkl Bookmark and Share
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