Synthesis 2018; 50(22): 4377-4382
DOI: 10.1055/s-0037-1609547
paper
© Georg Thieme Verlag Stuttgart · New York

Effect of γ-Substituted Proline Derivatives on the Performance of the Peptidic Catalyst H-dPro-Pro-Glu-NH2

Tobias Schnitzer
Laboratory of Organic Chemistry, D-CHAB, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: Helma.Wennemers@org.chem.ethz.ch
,
Laboratory of Organic Chemistry, D-CHAB, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: Helma.Wennemers@org.chem.ethz.ch
› Author Affiliations
Swiss National Science Foundation (Grant No. 200020_169423) and Fonds der Chemischen Industrie (Germany).
Further Information

Publication History

Received: 27 May 2018

Accepted after revision: 18 June 2018

Publication Date:
02 July 2018 (eFirst)

Dedicated to Professor Scott E. Denmark

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday

Abstract

Substituents at Cγ of proline are valuable probes to tune the trans/cis ratio of Xaa–Pro bonds. We investigated the effect of Cγ-substituents on the reactivity and stereoselectivity of the peptidic catalyst H-dPro-Pro-Glu-NH2. Derivatives that bear electron-withdrawing and -donating substituents (OH, F, N3, and SMe) at Cγ of the middle Pro-residue were examined. The results show that substituents at a 4R-configured Cγ hardly affect the stereoselectivity of the peptidic catalyst whereas substituents at a 4S-configured Cγ can be used to tune and improve the catalytic performance.

Supporting Information

 
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