Universität zu Köln

Klein, Marco T., Krause, Bernhard M., Neudorfl, Jorg-Martin, Kuhne, Ronald and Schmalz, Hans-Gunther (2022). Design and synthesis of a tetracyclic tripeptide mimetic frozen in a polyproline type II (PP2) helix conformation. Org. Biomol. Chem., 20 (47). S. 9368 - 9378. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1477-0539

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Abstract

A synthesis of the new tetracyclic scaffold ProM-19, which represents a XPP tripeptide unit frozen in a PPII helix conformation, was developed. As a key building block, N-Boc-protected ethyl (1S,3S,4R)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate was prepared through a diastereoselective aza-Diels-Alder reaction and subsequent hydrogenolytic removal of the chiral N-1-phenylethyl substituent under temporary protection of the double bond through dihydroxylation and reconstitution by Corey-Winter olefination. The target compound Boc-[ProM-19]-OMe was then prepared via subsequent peptide coupling and Ru-catalyzed ring-closing metathesis steps employing (S)-N-Boc-allylgylcine and cis-5-vinyl-proline methyl ester as additional building blocks. In addition, Ac-[2-Cl-Phe]-[Pro]-[ProM-19]-OMe was prepared by solution phase peptide synthesis as a potential ligand for the ena-VASP EVH1 domain.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Klein, Marco T. UNSPECIFIED UNSPECIFIED UNSPECIFIED Krause, Bernhard M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudorfl, Jorg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Kuhne, Ronald UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Gunther UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-663912
DOI:	10.1039/d2ob01857h
Journal or Publication Title:	Org. Biomol. Chem.
Volume:	20
Number:	47
Page Range:	S. 9368 - 9378
Date:	2022
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1477-0539
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language PROTEIN-PROTEIN INTERACTIONS; STEREOSELECTIVE-SYNTHESIS; PROLINE OLIGOPEPTIDES; ASYMMETRIC-SYNTHESIS; ACID-DERIVATIVES; SMALL MOLECULES; PEPTIDE; REARRANGEMENT; RECOGNITION; METATHESIS Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/66391