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Identifier 000429195
Title Στερεοεκλεκτικές αναγωγές α-φθορο-β-κετο εστέρων καταλυόμενες από NADPH- εξαρτώμενες κετορεδουκτάσες
Alternative Title Stereoselective reductions of α-fluoro-β-keto esters catalyzed by isolated NADPH-dependent ketoreductases
Author Μελαμπιανάκη, Σοφία Χ.
Thesis advisor Σμόνου, Ιουλία
Reviewer Στρατάκης, Εμμανουήλ
Νεοχωρίτης. Κωνσταντίνος
Abstract In the present thesis, the activity of various isolated ketoreductases on stereoselective bioreductions of perfluorinated carbonyl substrates was investigated for the synthesis of the corresponding optically pure alcohols. These compounds have been the focus of intensive research efforts, due to the benefits on physicochemical and bioactive properties induced in their molecular structure by a C-F bond. At first, the synthesis of 10 substrates in the form of α-fluoro-β-ketoesters is presented and then their enzymatic reductions using a series of NADPH-dependent ketoreductases for the synthesis of optically pure β-hydroxy-α-fluoro esters was studied. In particular, the stereoselective synthesis of a series of p-aryl substituted- αfluoro-β-ketoesters with different ester groups, has been successfully accomplished. Moreover, the fluorination via an electrophilic fluorination step has been achieved with high yields. The reaction conditions were optimized for the reduction reaction. For some substrates ketoreductases proved to be very efficient catalysts which showed good to high activity and excellent diastereo and enantioselectivity. Finally, a number of enzymes was determined that showed specific enantioselectivity without any dependence on the size of the ester group or the substituent on the aromatic ring.
Language Greek
Subject Biocatalysis
Chiral intermediates
Enzymatic reduction
Βιοκατάλυση
Ενζυμική αναγωγή
Χειρόμορφα ενδιάμεσα
β-hydroxy-α-fluoro esters
β-υδροξυ-αφθορο- εστέρες
Issue date 2020-03-27
Collection   School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
Permanent Link https://elocus.lib.uoc.gr//dlib/f/4/d/metadata-dlib-1585733294-744653-6651.tkl Bookmark and Share
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