Preparation of ß-Amino Acids and Synthesis of ß-Peptides with Novel Secondary Structures

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Preparation of beta-amino acids
and synthesis of beta-peptides
with novel secondary structures
Doctoral Thesis
Author(s):
Abele, Stefan
Publication date:
1999
Permanent link:
https://doi.org/10.3929/ethz-a-003824143
Rights / license:
In Copyright - Non-Commercial Use Permitted
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Diss. ETH No. 13203
Preparation of ß-Amino Acids and
Synthesis of ß-Peptides with Novel Secondary Structures
A dissertation submitted to the
SWISS FEDERAL INSTITUTE OF TECHNOLOGY
ZÜRICH
for the degree of
Doctor of Natural Sciences
Presented by
Stefan ABELE
Dipl. Chem. University of Konstanz
born January 21, 1970 in Waiblingen, Germany
Accepted on the recommendation of
Prof. Dr. Dieter Seebach, examiner
Prof. Dr. Donald Hilvert, co-examiner
Zürich 1999

For Isabelle
and my parents

I am deeply indebted to my
'Doktorvater'
Prof. Dr. Dieter Seebach
for his encouraging guidance and generous support over the course of my
thesis. The granted freedom for the design and execution of the projects, his
confidence, as well as his constant interest in the progress of my work have
made the past years a great and 'compact' experience.
fi!»--
M/
Parts of this thesis have been published:
Publications
G. Guichard, S. Abele, D. Seebach
'Preparation of N-Fmoc-Protected ß2- and ß3-Amino Acids and Their Use as
Building Blocks for the Solid-Phase Synthesis of ß-Peptides'
Helv. Chim. Acta 1998, 81, 187-206.
D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun,
J.L. Matthews, J.V. Schreiber, L. Oberer, U. Hommel, H. Widmer
'ß2- and ß3-Peptides with Proteinaceous Side Chains Synthesis and
-
Solution Structures of Constitutional Isomers, a Novel Helical Secondary
Structure and the Influence of Solvation and Hydrophobic Interactions on
Folding'
Helv. Chim. Acta 1998, 81, 932-982.
S. Abele, G. Guichard, D. Seebach
'(S)-ß3-Homolysine and (S)-ß3-Homoserine Containing ß-Peptides: CD
Spectra in Aqueous Solution'
Helv. Chim. Acta 1998, 81, 2141-2156.
D. Seebach, S. Abele, T. Sifferlen, M. Hänggi, S. Grüner, P. Seiler
'Preparation and Structure of ß-Peptides Consisting of Geminally
Disubstituted ß2'2- and ß3,3-Amino Acids. A Turn Motif for ß-Peptides'
Helv. Chim. Acta 1998, 81, 2218-2243.
D. Seebach, S. Abele, J.V. Schreiber, B. Martinoni, A.K. Nussbaum, H. Schild,
H. Schulz, H. Hennecke, R. Wössner, F. Bitsch
'Biological and Pharmacokinetic Studies with ß-Peptides'
Chimia 1998, 53(12), 734-739.
\
S. Abele, R. Wössner, F. Bitsch, D. Seebach
'New Secondary Structures of ß-Peptides and First Animal Experiments'
in 'Peptides 1998, Proceedings of the 25th European Peptide Symposium
-
August 30 September 4,1998 Budapest, Hungary)', Eds. S. Bajusz, F.
-
Hudecz, Akadémiai Kiadö, Budapest, 1999, 408-409.
D. Seebach, S. Abele, K. Gademann, B. Jaun
'Faltblätter und Schleifen von ß-Peptiden mit proteinogenen Seitenketten'
Angew. Chem. 1999,111, 1700-1703;
'Pleated Sheets and Turns of ß-Peptides with Proteinogenie Side Chains'
Angew. Chem. Int. Ed. 1999, 38, 1595-1597.
S. Abele, D. Seebach
'Preparation of Achiral and of Enantiopure Geminally Disubstituted ß-
Amino Acids for ß-Peptide Synthesis'
Eur. J. Org. Chem. 1999, in press.
S. Abele, K. Vögtli, D. Seebach
'Oligomers of ß2- and of ß3-Homoproline. What are the Secondary
Structures of ß-Peptides Lacking H-Bonds?'
Helv. Chim. Acta 1999, 82, in press.
S. Abele, P. Seiler, D. Seebach
'Synthesis, Crystal Structures, and Modelling of ß-Oligopeptides Consisting
of l-(Aminomethyl)cyclopropanecarboxylic Acid. Ribbon-Type Arrangement
of Eight-Membered H-Bonded Rings'
Helv. Chim. Acta 1999, 82, in press.
M. Werder, S. Abele, H. Hauser, D. Seebach
'Inhibition of Cholesterol Uptake by ß-Peptides'
in preparation.
Poster Presentations
T. Hintermann, S. Abele, B. Jaun, J.L. Matthews, J.V. Schreiber, L. Oberer, U.
Hommel, H. Widmer, D. Seebach
'Synthesis of small ß-peptides and investigation of their secondary
structure', 36th IUPAC Congress, 17.-22.8.1997, Geneva, Switzerland.
S. Abele, K. Gademann, D. Seebach
'Searching for new secondary structures of ß-peptides', 'Peptide and Protein
Drugs' Meeting, 2.10.1997, Zürich, Switzerland; Herbstversammlung der
Neuen Schweizerischen Chemischen Gesellschaft, 15.10.1997, Lausanne,
Switzerland.
M. Werder, S. Abele, D. Seebach, H. Hauser
'Inhibition of cholesterol uptake in the small intestinal brush border
membrane', D-BIOL Symposium ETH Zürich, 21.-23.5.1998, Davos,
Switzerland.
S. Abele, R. Wössner, F. Bitsch, M. Hänggi, S. Grüner, D. Seebach
'New secondary structures of ß-peptides. First animal experiments', 25'
European Peptide Symposium, 30.8.-4.9.1998, Budapest, Hungary.