☆ 4.0 Article

Optimized stereoselective and scalable synthesis of five-membered cyclic trans-β-amino acid building blocks via reductive amination

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Versatile Post-synthetic Modifications of Helical β-Peptide Foldamers Derived from a Thioether-Containing Cyclic β-Amino Acid

Danim Lim et al.

Summary: We introduce a novel cyclic β-amino acid, trans-(3S,4R)-4-aminotetrahydrothiophene-3-carboxylic acid (ATTC), as a versatile building block for designing peptide foldamers with controlled secondary structures. Our findings reveal that ATTC-containing foldamers can adopt 12-helical conformations similar to their isosteres and offer the possibility of fine-tuning their properties via post-synthetic modifications. In particular, chemoselective conjugation strategies demonstrate that ATTC provides unique post-synthetic modification opportunities, which expand their potential applications across diverse research areas.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Conformational Adaptation of β-Peptide Foldamers for the Formation of Metal-Peptide Frameworks

Seoneun Jeong et al.

Summary: This study presents the first metal-coordination-mediated assembly of beta-peptide foldamers with 12-helical folding propensity, resulting in unique entangled metal-peptide frameworks. The formation of network structures is accompanied by notable conformational distortions of the foldamer ligands. This work is expected to be an important benchmark for further structural evolution and mechanistic investigation in the field of metal-peptide frameworks.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Two-dimensional Zn(II) coordination polymer and hydrogen bond-mediated two-dimensional Cu(II) network based on trans-2-aminocyclopentanecarboxylate

Sung Hyun Yoo et al.

Summary: This study reported transition metal complexes from an unnatural beta-amino acid, showing different coordination modes and structural features.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Morphology Transformation of Foldamer Assemblies Triggered by Single Oxygen Atom on Critical Residue Switch

Byung-Chang Oh et al.

Summary: This study explores the challenging task of synthesizing well-defined peptidic materials via self-assembly for biocompatible functional materials. By introducing oxygen-containing beta-amino acid and systematic self-assembly studies, a minimal structural change that alters the self-assembled morphology is identified. The study demonstrates the potential for creating complex and biofunctional assemblies with nonspherical shapes through stepwise morphology transformation.

SMALL (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Water-Insensitive Synthesis of Poly-β-Peptides with Defined Architecture

Min Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Ligand-Enabled Monoselective β-C(sp3)-H Acyloxylation of Free Carboxylic Acids Using a Practical Oxidant

Zhe Zhuang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Foldamer Catalysis

Zebediah C. Girvin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Ribosomal synthesis and de novo discovery of bioactive foldamer peptides containing cyclic β-amino acids

Takayuki Katoh et al.

NATURE CHEMISTRY (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Foldectures: 3D Molecular Architectures from Self-Assembly of Peptide Foldamers

Sung Hyun Yoo et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Add to Collection

Article Chemistry, Medicinal

Peptides Containing β-Amino Acid Patterns: Challenges and Successes in Medicinal Chemistry

Chiara Cabrele et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Add to Collection

Review Biochemistry & Molecular Biology

Biosynthesis of natural products containing β-amino acids

Fumitaka Kudo et al.

NATURAL PRODUCT REPORTS (2014)

Add to Collection

Review Chemistry, Multidisciplinary

Application of alicyclic beta-amino acids in peptide chemistry

F Fulop et al.

CHEMICAL SOCIETY REVIEWS (2006)

Add to Collection

Article Chemistry, Organic

(+)- and (-)-2-aminocyclobutane-1-carboxylic acids and their incorporation into highly rigid β-peptides:: Stereoselective synthesis and a structural study

S Izquierdo et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

Add to Collection

Article Chemistry, Organic

Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

ME Bunnage et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2004)

Add to Collection

Review Biochemistry & Molecular Biology

β-amino acids:: Versatile peptidomimetics

DL Steer et al.

CURRENT MEDICINAL CHEMISTRY (2002)

Add to Collection

Article Chemistry, Organic

An efficient route to either enantiomer of trans-2-aminocyclopentanecarboxylic acid

PR LePlae et al.

JOURNAL OF ORGANIC CHEMISTRY (2001)

Add to Collection

Article Chemistry, Organic

An efficient route to either enantiomer of orthogonally protected trans-3-aminopyrrolidine-4-carboxylic acid

HS Lee et al.

JOURNAL OF ORGANIC CHEMISTRY (2001)

Add to Collection

© Peeref 2019-2024. All rights reserved.