Nonribosomal peptide synthesis—principles and prospects

RD Süssmuth, A Mainz - Angewandte Chemie International …, 2017 - Wiley Online Library
Nonribosomal peptide synthetases (NRPSs) are large multienzyme machineries that
assemble numerous peptides with large structural and functional diversity. These peptides …

Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds

CT Walsh, RV O'Brien, C Khosla - … Chemie International Edition, 2013 - Wiley Online Library
Freestanding nonproteinogenic amino acids have long been recognized for their
antimetabolite properties and tendency to be uncovered to reactive functionalities by the …

Heteroatom–heteroatom bond formation in natural product biosynthesis

AJ Waldman, TL Ng, P Wang, EP Balskus - Chemical reviews, 2017 - ACS Publications
Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X,
where X= N, O, S, and P) are a small yet intriguing group of metabolites. The reactivity and …

Targeted and logical discovery of piperazic acid-bearing natural products based on genomic and spectroscopic signatures

D Shin, WS Byun, S Kang, I Kang, ES Bae… - Journal of the …, 2023 - ACS Publications
A targeted and logical discovery method was devised for natural products containing
piperazic acid (Piz), which is biosynthesized from ornithine by l-ornithine N-hydroxylase …

The hidden enzymology of bacterial natural product biosynthesis

TA Scott, J Piel - Nature Reviews Chemistry, 2019 - nature.com
Bacterial natural products display astounding structural diversity, which, in turn, endows
them with a remarkable range of biological activities that are of significant value to modern …

A heme-dependent enzyme forms the nitrogen–nitrogen bond in piperazate

YL Du, HY He, MA Higgins, KS Ryan - Nature Chemical Biology, 2017 - nature.com
Molecules containing a nitrogen–nitrogen (N–N) linkage have a variety of structures and
biological activities; however, no enzyme has yet been demonstrated to catalyze N–N bond …

Free piperazic acid as a precursor to nonribosomal peptides

ZW Wei, H Niikura, KD Morgan… - Journal of the …, 2022 - ACS Publications
Piperazic acid (Piz) is a nonproteinogenic amino acid possessing a rare nitrogen–nitrogen
bond. However, little is known about how Piz is incorporated into nonribosomal peptides …

Beyond ethylmalonyl-CoA: the functional role of crotonyl-CoA carboxylase/reductase homologs in expanding polyketide diversity

MC Wilson, BS Moore - Natural product reports, 2012 - pubs.rsc.org
Covering: up through August 2011 This review covers the emerging biosynthetic role of
crotonyl-CoA carboxylase/reductase (CCR) homologs in extending the structural and …

Discovery of unprecedented hydrazine-forming machinery in bacteria

K Matsuda, T Tomita, K Shin-Ya… - Journal of the …, 2018 - ACS Publications
Recent studies described several different routes that facilitate nitrogen–nitrogen bond
formation in natural product biosynthesis. We report herein the identification of …

Piperazic acid-containing natural products: structures and biosynthesis

KD Morgan, RJ Andersen, KS Ryan - Natural Product Reports, 2019 - pubs.rsc.org
Covering: up to the end of 2018 Piperazic acid is a cyclic hydrazine and a non-proteinogenic
amino acid found in diverse non-ribosomal peptide (NRP) and hybrid NRP–polyketide (PK) …