TY  - JOUR
AU  - Hegedüs, Zsófia
AU  - Wéber, Edit
AU  - Kriston-Pál, Éva
AU  - Makra, Ildikó
AU  - Czibula, Ágnes
AU  - Monostori, Éva
AU  - Martinek, Tamás
TI  - Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity
JF  - JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
J2  - J AM CHEM SOC
VL  - 135
PY  - 2013
IS  - 44
SP  - 16578
EP  - 16584
PG  - 7
SN  - 0002-7863
DO  - 10.1021/ja408054f
UR  - https://m2.mtmt.hu/api/publication/2459240
ID  - 2459240
AB  - The principles of beta-sheet folding and design for alpha-peptidic sequences are well established, while those for sheet mimetics containing homologated amino acid building blocks are still under investigation. To reveal the structure-function relations of beta-amino-acid-containing foldamers, we followed a top-down approach to study a series of alpha/beta-peptidic analogs of anginex, a beta-sheet-forming antiangiogenic peptide. Eight anginex analogs were developed by systematic alpha --> beta(3) substitutions and analyzed by using NMR and CD spectroscopy. The foldamers retained the beta-sheet tendency, though with a decreased folding propensity. beta-Sheet formation could be induced by a micellar environment, similarly to that of the parent peptide. The destructuring effect was higher when the alpha --> beta(3) exchange was located in the beta-sheet core. Analysis of the beta-sheet stability versus substitution pattern and the local conformational bias of the bulky beta(3)V and beta(3)I residues revealed that a mismatch between the H-bonding preferences of the alpha- and beta-residues played a minor role in the structure-breaking effect. Temperature-dependent CD and NMR measurements showed that the hydrophobic stabilization was scaled-down for the alpha/beta-peptides. Analysis of the biological activity of the foldamer peptides showed that four anginex derivatives dose-dependently inhibited the proliferation of a mouse endothelial cell line. The alpha --> beta(3) substitution strategy applied in this work can be a useful approach to the construction of bioactive beta-sheet mimetics with a reduced aggregation tendency and improved pharmacokinetic properties.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Fülöp, Ferenc
AU  - Martinek, Tamás
AU  - Tóth, Gábor
TI  - Application of alicyclic beta-amino acids in peptide chemistry
JF  - CHEMICAL SOCIETY REVIEWS
J2  - CHEM SOC REV
VL  - 35
PY  - 2006
IS  - 4
SP  - 323
EP  - 334
PG  - 12
SN  - 0306-0012
DO  - 10.1039/B501173F
UR  - https://m2.mtmt.hu/api/publication/1012938
ID  - 1012938
N1  - Megjegyzés-21956224
Z9: 133
WC: Chemistry, Multidisciplinary
Megjegyzés-21957808
Z9: 133
WC: Chemistry, Multidisciplinary
CAplus AN 2006:279672; MEDLINE PMID: 16565749 (Journal; General Review; Article; Research Support, Non-U.S. Gov't; Review);
AB  - The self-organizing beta-peptides have attracted considerable interest in the fields of foldamer chemistry and biochemistry. These compounds exhibit various stable secondary structure motifs that can be exploited to construct biologically active substances and nanostructured tertiary structures. The secondary structures can be controlled via the beta-amino acid sequence, and cyclic beta-amino acid residues play a crucial role in the design. The most important procedures for the preparation of cyclic beta-amino acid monomers and peptides are discussed in this tutorial review. Besides the secondary structure design principles, the methods of folded structure detection are surveyed.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Martinek, Tamás
AU  - Tóth, Gábor
AU  - Vass, Elemér
AU  - Hollósi, Miklós
AU  - Fülöp, Ferenc
TI  - cis-2-aminocyclopentanecarboxylic acid oligomers adopt a sheetlike structure: Switch from helix to nonpolar strand
JF  - ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
J2  - ANGEW CHEM INT EDIT
VL  - 41
PY  - 2002
IS  - 10
SP  - 1718
EP  - 1721
PG  - 4
SN  - 1433-7851
DO  - 10.1002/1521-3773(20020517)41:10<1718::AID-ANIE1718>3.0.CO;2-2
UR  - https://m2.mtmt.hu/api/publication/1013825
ID  - 1013825
LA  - English
DB  - MTMT
ER  -