Asymmetric 1,4‐Addition Reactions Catalyzed by N‐Terminal Thiourea‐Modified Helical l‐Leu Peptide with Cyclic Amino Acids

K Sato, T Umeno, A Ueda, T Kato… - … –A European Journal, 2021 - Wiley Online Library
N‐terminal thiourea‐modified l‐Leu‐based peptide {(3, 5‐diCF3Ph) NHC (= S)‐(l‐Leu‐l‐
Leu‐Ac5c) 2‐OMe} with five‐membered ring α, α‐disubstituted α‐amino acids (Ac5c) …

E-Selective Ring-Closing Metathesis in α-Helical Stapled Peptides Using Carbocyclic α,α-Disubstituted α-Amino Acids

A Ueda, Y Makura, S Kakazu, T Kato, T Umeno… - Organic …, 2022 - ACS Publications
We present an E-selective ring-closing metathesis reaction in α-helical stapled peptides at
positions i and i+ 4. The use of two chiral carbocyclic α, α-disubstituted α-amino acids,(1 S, 3 …

Helical foldamer-catalyzed enantioselective 1, 4-addition reaction of dialkyl malonates to cyclic enones

T Umeno, A Ueda, M Doi, T Kato, M Oba, M Tanaka - Tetrahedron Letters, 2019 - Elsevier
The introduction of a five-membered ring α, α-disubstituted α-amino acid into l-Leu-based
heptapeptides preferentially induced right-handed (P) helical structures. Using 5∼ 20 mol …

[HTML][HTML] Conformational Analysis and Organocatalytic Activity of Helical Stapled Peptides Containing α-Carbocyclic α, α-Disubstituted α-Amino Acids

A Iyoshi, A Ueda, T Umeno, T Kato, K Hirayama, M Doi… - Molecules, 2024 - mdpi.com
Conformational freedom-restricted peptides, such as stapled peptides, play a crucial role in
the advancement of functional peptide development. We synthesized stapled octapeptides …

Six-membered ring systems: With O and/or S atoms

CMM Santos, AMS Silva - Progress in Heterocyclic Chemistry, 2021 - Elsevier
The most interesting chemistry published in 2020 on the synthesis of O-and S-six-membered
heterocycles is reviewed. This personal overview is focused on the developments made on …

Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling

A Ueda, M Higuchi, K Sato, T Umeno, M Tanaka - Molecules, 2020 - mdpi.com
We designed and synthesized helical short oligopeptides with an l-proline on the N-terminus
and hydrocarbon stapling on the side chain. Side-chain stapling is a frequently used method …

X-ray Crystallographic Structure of α-Helical Peptide Stabilized by Hydrocarbon Stapling at i,i + 1 Positions

Y Makura, A Ueda, T Kato, A Iyoshi, M Higuchi… - International Journal of …, 2021 - mdpi.com
Hydrocarbon stapling is a useful tool for stabilizing the secondary structure of peptides.
Among several methods, hydrocarbon stapling at i, i+ 1 positions was not extensively …