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

Tobias Schnitzer; Helma Wennemers

doi:10.1055/s-0037-1609547

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(22): 4377-4382
DOI: 10.1055/s-0037-1609547

paper

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

,

Helma Wennemers *

Laboratory of Organic Chemistry, D-CHAB, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland eMail: Helma.Wennemers@org.chem.ethz.ch

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Abstract

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Dedicated to Professor Scott E. Denmark

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

Key words

proline - peptides - trans/cis isomerization - organocatalysis - conjugate addition reactions

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