Expanding the scope of enzyme catalysis with β-amino acids and metal cofactors

182 Pages·2014·4.16 MB·English

ETH Library
Expanding the scope of enzyme
catalysis with β-amino acids and
metal cofactors
Doctoral Thesis
Author(s):
Mayer, Clemens
Publication date:
2014
Permanent link:
https://doi.org/10.3929/ethz-a-010104099
Rights / license:
In Copyright - Non-Commercial Use Permitted
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DISS. ETH N° 21658

Expanding the scope of enzyme catalysis
with β-amino acids and metal cofactors
A thesis submitted to attain the degree of
DOCTOR OF SCIENCES of ETH ZÜRICH
(Dr. sc. ETH Zurich)
presented by
CLEMENS MAYER
Dipl. Ing., Technische Universität Graz
born on 06.05.1985
citizen of Austria
accepted on the recommendation of
Prof. Dr. Donald Hilvert, examiner

Prof. Dr. Helma Wennemers, co-examiner
2014

I would take the awe of understanding over the awe of ignorance
any day.
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ACKNOWLEDGMENTS
Experiencing the screams, manic laughter, somber tragedies, and the sense of
awe and agony that underpins the doctorial life span would not have been such
a pleasure without the help and support of the kind people around me. This
Acknowledgment section provides me with an opportunity to say thank you to
a few of them.
I am grateful to my PhD supervisor, Don Hilvert, who kept a sense of humor
when I had lost mine and attempted – with his maddening attention to detail –
to teach me the English language and how to punctuate prose. His constant
support and the granted freedom were the cornerstones to the success of my
PhD thesis.
I would also like to thank Helma Wennemers for agreeing to co-examine my
thesis and Peter Kast for his advice to every biological problem I encountered
over the past 5½ years. I am indebted to Sam Gellman for providing his
unmatched knowledge about α/β-peptides to the work described in Chapter 4
and his group for providing cyclic building blocks when they were needed. I
would like to further acknowledge Novartis for financial support.
Particular thanks go to my undergraduate students Andreas Küchler, Raoul
Rosenthal, Anja Pabst, Thomas Wucherpfennig, Marjorie Corrales Carnero, and
Benita Heiz for their contributions and their interest in my research.
Over the years, I benefited tremendously from the great atmosphere in the
Hilvert group. Foremost, I am grateful to Dennis Gillingham and Manuel Müller
V
for teaching me the basics of science & life in the Hilvert group and for showing
me the ins and outs of the day & nightlife in Zürich. From the plethora of
undergrads, PhD students, postdocs, visiting scientists, etc., that I had the
pleasure to meet, I would like to thank those who accompanied me for most of
my time at ETH: Hajo Kries for his open tap policy concerning lunch & coffee
invitations, when I once again did not have any money, Nathalie Preiswerk for
her honesty and friendship, Richard Obexer for his delicious cooking, Cindy
Schulenburg and An Vandemeulebroucke for taking the time to listen and cheer
me up, David Niquille and Sabine Studer for continuing some of the projects
described in this thesis, Reinhard Zschoche for providing milk for my coffee,
and Clement Dince for making day-to-day lab life and the after-work parties
such an enjoyable experience.
I am deeply thankful for all the wonderful friendships in Zürich and Austria
that make my life such a pleasure to live. In this respect, special thanks goes to
Johannes Reiter and Tobias Abel for having put up with me for such a long time.
Lastly, I would like to thank my family for all the support and my Natalie for
always being there for me.
VI

Parts of this thesis have been
published

A genetically-encodable ligand for transfer hydrogenation
Mayer, C.; Hilvert, D.
Eur. J. Org. Chem., 2013, 17, 3427-3431

An artificial metalloenzyme for olefin metathesis
Mayer, C.; Gillingham, D. G.; Ward, T. R.; Hilvert, D.,
Chem. Comm. 2011, 47 (44), 12068-12070
IX