ArticleAngewandte Chemie (International ed. in English)2018
In Vitro Biosynthesis of the Nonproteinogenic Amino Acid Methoxyvinylglycine.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
13 citing papers in PubMed, 33 citations in OpenAlex.
- PEARL-Catalyzed Peptide Bond Formation after Chain Reversal by Ureido-Forming Condensation Domains.ACS central science · 2024Article
- Structural insights into the substrate-bound condensation domains of non-ribosomal peptide synthetase AmbB.Scientific reports · 2022Article
- Nonribosomal Peptide Synthesis Definitely Working Out of the Rules.Microorganisms · 2022Review
- Acyl Donor Stringency and Dehydroaminoacyl Intermediates in β-Lactam Formation by a Non-ribosomal Peptide Synthetase.ACS chemical biology · 2021Article
- Structures of a non-ribosomal peptide synthetase condensation domain suggest the basis of substrate selectivity.Nature communications · 2021Article
- Evolutionary and functional analysis of an NRPS condensation domain integrates β-lactam, ᴅ-amino acid, and dehydroamino acid synthesis.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Genome Mining and Metabolomics Uncover a Rare d-Capreomycidine Containing Natural Product and Its Biosynthetic Gene Cluster.ACS chemical biology · 2020Article
- Exploring modular reengineering strategies to redesign the teicoplanin non-ribosomal peptide synthetase.Chemical science · 2020Article
- A proof-reading mechanism for non-proteinogenic amino acid incorporation into glycopeptide antibiotics.Chemical science · 2019Article
- Discovery and Biosynthesis of Azabicyclene, a Conserved Nonribosomal Peptide in Pseudomonas aeruginosa.Organic letters · 2019Article
- Targeted Rediscovery and Biosynthesis of the Farnesyl-Transferase Inhibitor Pepticinnamin E.Chembiochem : a European journal of chemical biology · 2019Article
- Article
- The biosynthetic implications of late-stage condensation domain selectivity during glycopeptide antibiotic biosynthesis.Chemical science · 2019Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Oxyvinylglycines are a family of nonproteinogenic amino acids featuring an essential vinyl ether conferring mechanism-based inhibition of pyridoxal phosphate enzymes. The gene clusters for a few oxyvinylglycines are known, yet the biosynthetic origin of the vinyl ether is elusive. The in vitro biosynthesis of methoxyvinylglycine or l-2-amino-4-methoxy-trans-3-butenoic acid (AMB) is reported. It is shown that AMB is made from glutamate as an alanyl-AMB dipeptide and the rationale is provided for the N-term Ala. Using a chemical capture method, the order and timing of the modifications on non-ribosomal peptide synthetase (NRPS)-bound substrates was determined, including a cryptic hydroxylation of the Glu β-carbon. Eliminating this hydroxy group likely generates a key α,β-dehydroamino acid intermediate that facilitates decarboxylation. This work sheds light on vinyl ether biosynthesis and uncovers new NRPS chemistry.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.