Synthesis of Peptides by Silver‐Promoted Coupling of Carboxylates and Thioamides: Mechanistic Insight from Computational Studies

CA Hutton, J Shang, U Wille - Chemistry–A European Journal, 2016 - Wiley Online Library
The mechanism of the recently described N→ C direction peptide synthesis through silver‐
promoted coupling of N‐protected amino acids with thioacetylated amino esters was …

A new method for peptide synthesis in the N→ C direction: amide assembly through silver-promoted reaction of thioamides

A Pourvali, JR Cochrane, CA Hutton - Chemical communications, 2014 - pubs.rsc.org
The Ag (I)-promoted coupling of amino acids and peptides with amino ester thioamides
generates peptide imides without epimerisation. The peptide imides undergo regioselective …

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

V Adebomi, M Sriram, X Streety, M Raj - Organic Letters, 2021 - ACS Publications
Here we solve a long-standing challenge of the site-selective modification of secondary
amides and present a simple two-step, metal-free approach to selectively modify a particular …

Amide bond formation: beyond the dilemma between activation and racemisation

W Muramatsu, T Hattori, H Yamamoto - Chemical Communications, 2021 - pubs.rsc.org
The development of methods for amide bond formation without recourse to typical
condensation reagents has become an emerging research area and has been actively …

Effect of copper salts on peptide bond formation using peptide thioesters

R Ingenito, H Wenschuh - Organic Letters, 2003 - ACS Publications
In the present paper, systematic studies revealed that Cu (I) salts in general and Cu (II) salts
under certain circumstances promote effective reaction between peptide thiol esters and the …

Amine Activation:“Inverse” Dipeptide Synthesis and Amide Function Formation through Activated Amino Compounds

E Tosi, JM Campagne… - The Journal of Organic …, 2022 - ACS Publications
A copper (II)/HOBt-catalyzed procedure for the synthesis of dipeptides and “general” amides
has been developed using microwave irradiation to considerably hasten the reaction. As an …

Metal-free approach for hindered amide-bond formation with hypervalent iodine (iii) reagents: application to hindered peptide synthesis

HJ Lee, X Huang, S Sakaki, K Maruoka - Green Chemistry, 2021 - pubs.rsc.org
A new bio-inspired approach is reported for amide and peptide synthesis using α-amino
esters that possess a potential activating group (PAG) at the ester residue. To activate the …

Fmoc-Based Synthesis of Peptide Thioacids for Azide Ligations via 2-Cyanoethyl Thioesters

R Raz, J Rademann - Organic letters, 2012 - ACS Publications
Rapid and efficient preparation of peptide thioacids from 2-cyanoethyl peptide thioesters has
been accomplished. S-2-Cyanoethyl peptide thioesters were obtained cleanly without the …

Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C (sp 3)–H arylation

L Liu, YH Liu, BF Shi - Chemical Science, 2020 - pubs.rsc.org
Amino acids and peptides with bulky side chains are of significant importance in organic
synthesis and modern medicinal chemistry. The efficient synthesis of these molecules with …

Understanding the structure/reactivity of aminium/uronium salts as coupling reagents in peptide synthesis

JM Bofill, F Albericio - Tetrahedron Letters, 1999 - Elsevier
Coupling reagents based on onium (aminium/uronium) salts based on HOBt and HOAt are
more frequently used in solid-phase peptide synthesis than the classical carbodiimide …