Macrocyclization and backbone modification in RiPP biosynthesis

H Lee, WA Van Der Donk - Annual review of biochemistry, 2022 - annualreviews.org
The past decade has seen impressive advances in understanding the biosynthesis of
ribosomally synthesized and posttranslationally modified peptides (RiPPs). One of the most …

Dehydroamino acid residues in bioactive natural products

S Wang, K Wu, YJ Tang, H Deng - Natural Product Reports, 2024 - pubs.rsc.org
Covering: 2000 to up to 2023 α, β-Dehydroamino acids (dhAAs) are unsaturated
nonproteinogenic amino acids found in a wide array of naturally occurring peptidyl …

Class V lanthipeptide cyclase directs the biosynthesis of a stapled peptide natural product

ZF Pei, L Zhu, R Sarksian… - Journal of the …, 2022 - ACS Publications
Lanthipeptides are a class of cyclic peptides characterized by the presence of one or more
lanthionine (Lan) or methyllanthionine (MeLan) thioether rings. These cross-links are …

Mechanistic studies on dehydration in class V lanthipeptides

H Liang, IJ Lopez, M Sánchez-Hidalgo… - ACS chemical …, 2022 - ACS Publications
Lanthipeptides are ribosomally synthesized and post-translationally modified peptides
characterized by lanthionine (Lan) and/or methyllanthionine (MeLan) residues. Four classes …

Association of Radical Chemistry with LanD Flavoprotein Activity for C‐Terminal Macrocyclization of a Ribosomal Peptide by Formation of an Unsaturated Thioether …

B Cheng, J Huang, Y Duan… - Angewandte Chemie …, 2023 - Wiley Online Library
LanD flavoproteins catalyze oxidative decarboxylation of the C‐terminal Cys residue of a
peptide to produce an enethiol. This enethiol is highly reactive and can be coupled with an …

Total in vitro biosynthesis of the thioamitide thioholgamide and investigation of the pathway

A Sikandar, M Lopatniuk, A Luzhetskyy… - Journal of the …, 2022 - ACS Publications
Thioholgamides are ribosomally synthesized and posttranslationally modified peptides
(RiPPs), with potent activity against cancerous cell lines and an unprecedented structure …

Aminovinyl cysteine containing peptides: a unique motif that imparts key biological activity

ES Grant-Mackie, ET Williams, PWR Harris… - Jacs Au, 2021 - ACS Publications
Natural products that contain distinctive chemical functionality can serve as useful starting
points to develop Nature's compounds into viable therapeutics. Peptide natural products, an …

Hijacking a linaridin biosynthetic intermediate for lanthipeptide production

L Chu, J Cheng, C Zhou, T Mo, X Ji, T Zhu… - ACS Chemical …, 2022 - ACS Publications
Linaridins and lanthipeptides are two classes of natural products belonging to the
ribosomally synthesized and posttranslationally modified peptide (RiPP) superfamily …

Enzymatic Generation of Thioaldehyde Motifs by Flavin-Dependent Cysteine Decarboxylases for Peptide Bioconjugation and Macrocyclization

Y Xia, Y Yi, Y Shi, T Long, H Wang - Organic Letters, 2023 - ACS Publications
Thioaldehyde is a highly electrophilic group under aqueous conditions and can be
generated via oxidative enzymatic modifications of cysteine residues in peptides and …

Unusual cysteine modifications in natural product biosynthesis

Y Gao, Y Zhu, T Awakawa, I Abe - RSC Chemical Biology, 2024 - pubs.rsc.org
L-Cysteine is a highly reactive amino acid that is modified into a variety of chemical
structures, including cysteine sulfinic acid in human metabolic pathways, and sulfur …