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
Full text not available from this repository.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: |
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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: |
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URI: | http://kups.ub.uni-koeln.de/id/eprint/66391 |
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