Reuter, Cedric, Kleczka, Margarethe, de Mazancourt, Sarah, Neudoerfl, Joerg-Martin, Kuehne, Ronald and Schmalz, Hans-Guenher (2014). Stereoselective Synthesis of Proline- Derived Dipeptide Scaffolds ( ProM-3 and ProM-7) Rigidified in a PPII Helix Conformation. Eur. J. Org. Chem., 2014 (13). S. 2664 - 2668. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

Following a peptide coupling/metathesis-based strategy, the two diastereomeric scaffolds ProM-3 and ProM-7 were stereoselectively synthesized (as 9-fluorenylmethoxycarbonyl derivatives), and their configuration was unambiguously proven by means of X-ray crystallography. The required dehydroisoleucine building blocks were prepared by applying the enantioselective Kazmaier-Claisen rearrangement. The target compounds represent dipeptide analogs rigidified in a PPII helix conformation, which are of interest for the development of new proteomimetics that selectively bind to protein domains specialized in the recognition of ligands adopting a PPII helix secondary structure.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Reuter, CedricUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kleczka, MargaretheUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
de Mazancourt, SarahUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kuehne, RonaldUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuenherUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-439986
DOI: 10.1002/ejoc.201301875
Journal or Publication Title: Eur. J. Org. Chem.
Volume: 2014
Number: 13
Page Range: S. 2664 - 2668
Date: 2014
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1099-0690
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PROTEIN-PROTEIN INTERACTIONS; SMALL MOLECULES; AMINO-ACIDS; LIGANDS; INHIBITION; MODULATION; PEPTIDES; DESIGN; ACTINMultiple languages
Chemistry, OrganicMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/43998

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