Data di Pubblicazione:
2009
Citazione:
Synthesis of chiral bioactive molecules by Catalytic Asymmetric Reduction / D.s. Zerla ; Tutor: Edoardo Cesarotti ; Coordinatore: Franco Cozzi. DIPARTIMENTO DI CHIMICA INORGANICA, METALLORGANICA E ANALITICA "Lamberto Malatesta", 2009 Dec 16. 22. ciclo, Anno Accademico 2008/2009.
Abstract:
Synthesis of chiral bioactive molecules by Catalytic Asymmetric Reduction
1) Carnosine is an endogenous dipeptide (β-alanyl-L-histidine) presents in the human muscles and nerve tissue which has a protective and detoxifying effect on the toxic metabolites. D-Carnosine is cited as an equivalent to L-carnosine, but due to its durability to hydrolysis by the carnosinases, seems to produce better therapeutic results than the L-form. To study the bioavailability and pharmacokinetic profile of D-carnosine, a deuterium labelled derivative is needed.
The optically active D or L histidine for carnosine synthesis can be preparated by asymmetric hydrogenation of the corresponding dehydro-aminoacid using Rh(I)-diphosphine complexes in presence of strong non coordinating acid.
2) The great success of Diphosphine-Ru systems in the reduction of
funzionalized ketones was reappraised by low activity in the
hydrogenation of un-funzionalized ketones which need the presence of an ancillary ligand in the complex for its reduction. In this thesis the effect of a rigid chirality on the ancillary diamine ligand using an ampy analogue, 8-amino-5,6,7,8-hydro-quinoline (CAMPY), will be studied in asymmetric hydrogenation and asymmetric transfer hydrogenation reactions.
Tipologia IRIS:
13 - Tesi di dottorato discussa entro ottobre 2010
Elenco autori:
D.S. Zerla
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