Radical‐based synthesis and modification of amino acids

FJ Aguilar Troyano, K Merkens, K Anwar… - Angewandte Chemie …, 2021 - Wiley Online Library
Amino acids (AAs) are key structural motifs with widespread applications in organic
synthesis, biochemistry, and material sciences. Recently, with the development of milder …

Applications of thiol-ene chemistry for peptide science

MD Nolan, EM Scanlan - Frontiers in chemistry, 2020 - frontiersin.org
Radical thiol-ene chemistry has been demonstrated for a range of applications in peptide
science, including macrocyclization, glycosylation and lipidation amongst a myriad of others …

Alkene 1, 1-difunctionalizations via organometallic-radical relay

D Wu, W Kong, Y Bao, D Zhao, Y Li, G Yin - Nature Catalysis, 2023 - nature.com
Radical reactions play an important role in modern organic synthetic chemistry. The
generation of carbon radicals from the homolytic cleavage of carbon–metal bonds has been …

Stereoselective alkyl C-glycosylation of glycosyl esters via anomeric C–O bond homolysis: efficient access to C-glycosyl amino acids and C-glycosyl peptides

A Chen, S Zhao, Y Han, Z Zhou, B Yang, LG Xie… - Chemical …, 2023 - pubs.rsc.org
C-Glycosyl peptides possess excellent metabolic stability and therapeutic properties and
thus play critical roles in biological studies as well as drug discoveries. However, the limited …

Combining flavin photocatalysis with parallel synthesis: a general platform to optimize peptides with non-proteinogenic amino acids

JR Immel, M Chilamari, S Bloom - Chemical Science, 2021 - pubs.rsc.org
Most peptide drugs contain non-proteinogenic amino acids (NPAAs), born out through
extensive structure–activity relationship (SAR) studies using solid-phase peptide synthesis …

Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes

P Palamini, EMD Allouche, J Waser - Organic Letters, 2023 - ACS Publications
An iron-catalyzed alkylazidation of dehydroamino acids using peroxides as alkyl radical
precursors is described. Non-natural azidated amino esters bearing an α-alkyl chain could …

Allenamides as a Powerful Tool to Incorporate Diversity: Thia‐Michael Lipidation of Semisynthetic Peptides and Access to β‐Keto Amides

TU Na, V Sander, AJ Davidson, R Lin… - Angewandte Chemie …, 2024 - Wiley Online Library
Lipopeptides are an important class of biomolecules for drug development. Compared with
conventional acylation, a chemoselective lipidation strategy offers a more efficient strategy …

Synthesis of γ-oxo-α-amino acids via radical acylation with carboxylic acids

K Merkens, FJ Aguilar Troyano, K Anwar… - The Journal of …, 2021 - ACS Publications
Herein we present a highly efficient, light-mediated, deoxygenative protocol to access γ-oxo-
α-amino acid derivatives. This radical methodology employs photoredox catalysis, in …

Thiyl radicals: versatile reactive intermediates for cyclization of unsaturated substrates

DM Lynch, EM Scanlan - Molecules, 2020 - mdpi.com
Sulfur centered radicals are widely employed in chemical synthesis, in particular for alkene
and alkyne hydrothiolation towards thioether bioconjugates. The steadfast radical chain …

Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

M Zhang, P He, Y Li - Chemical Research in Chinese Universities, 2021 - Springer
A s one of the most common unnatural amino acids (uAAs), α, β-dehydroamino acids (α, β-
dhAAs) can be found in various ribosomally synthesized and post-translationally modified …