Peptide macrocyclization by transition metal catalysis

DG Rivera, GM Ojeda-Carralero, L Reguera… - Chemical Society …, 2020 - pubs.rsc.org
Peptide macrocyclization has traditionally relied on lactam, lactone and disulfide bond-
forming reactions that aim at introducing conformational constraints into small peptide …

Indole-Based Macrocyclization by Metal-Catalyzed Approaches

SR Cheekatla, D Barik, G Anand, R Mol KM, M Porel - Organics, 2023 - mdpi.com
This review is dedicated to the different varieties of macrocycles synthesis bearing indole
units in their architecture by metal-catalyzed strategies. The progress of the new …

Mild and chemoselective thioacylation of amines enabled by the nucleophilic activation of elemental sulfur

M Saito, S Murakami, T Nanjo… - Journal of the …, 2020 - ACS Publications
A mild and chemoselective method for the thioacylation of amines using α-keto acids and
elemental sulfur has been developed. The key to the success of this transformation is the …

A general strategy to install amidine functional groups along the peptide backbone

EA O'Brien, KK Sharma, J Byerly-Duke… - Journal of the …, 2022 - ACS Publications
Amidines are a structural surrogate for peptide bonds, yet have received considerably little
attention in peptides due to limitations in existing methods to access them. The synthetic …

Site Specific Preparation of N‐Glycosylated Peptides: Thioamide‐Directed Activation of Aspartate

AB Taresh, CA Hutton - Angewandte Chemie, 2022 - Wiley Online Library
Site Specific Preparation of N‐Glycosylated Peptides: Thioamide‐Directed Activation of
Aspartate - Taresh - 2022 - Angewandte Chemie - Wiley Online Library Skip to Article Content …

Depsipeptide synthesis using a late-stage Ag (i)-promoted macrolactonisation of peptide thioamides

S Shabani, CA Hutton - Chemical Communications, 2021 - pubs.rsc.org
Macrolactonisation of peptides to generate cyclic depsipeptides is often challenging due to
the low nucleophilicity of hydroxyl groups, epimerisation, cyclodimerisation, and potential …

Ring expansion of thiolactams via imide intermediates: An amino acid insertion strategy

J Shang, VJ Thombare, CL Charron… - … A European Journal, 2021 - Wiley Online Library
The AgI‐promoted reaction of thiolactams with N‐Boc amino acids yields an N‐(α‐
aminoacyl) lactam that can rearrange through an acyl transfer process. Boc‐deprotection …

Zn-catalyzed nicotinate-directed transamidations in peptide synthesis

C Hollanders, E Renders, C Gadais, D Masullo… - ACS …, 2020 - ACS Publications
A chemoselective and catalytic transamidation for peptide synthesis is described.
Transamidation under Zn catalysis is chemoselectively achieved by amino acid …

Modern Macrolactonization Techniques

M Van Hoof, G Force, D Lebœuf - Synthesis, 2024 - thieme-connect.com
The study of macrolactonization processes has been a steady endeavor for synthetic
chemists to access macrocycles that are fundamental in the development of numerous high …

A bottom-up approach to preserve thioamide residue stereochemistry during Fmoc solid-phase peptide synthesis

LA Camacho III, BJ Lampkin, B VanVeller - Organic letters, 2019 - ACS Publications
Thioamides are useful biophysical probes for the study of peptide structure and folding. The
α-C stereochemistry of thioamide amino acids, however, is easily epimerized during solid …