ArticleJournal of the American Chemical Society2016
Biosynthesis of Strained Piperazine Alkaloids: Uncovering the Concise Pathway of Herquline A.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 65 citations in OpenAlex.
- Revolutionizing microbial treasure troves: innovative strategies for natural products discovery.Natural products and bioprospecting · 2026Review
- Gymnosperm-specific CYP90Js enable biflavonoid biosynthesis and microbial production of amentoflavone.Nature communications · 2025Article
- Tuning and functionalization of logic gates for time resolved programming of bacterial populations.Nucleic acids research · 2025Article
- Fragment-Guided Genome Mining of Octacyclic Cyclophane Alkaloids from Fungi.Journal of the American Chemical Society · 2024Article
- Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.Angewandte Chemie (International ed. in English) · 2023Article
- Characterization and catalytic investigation of fungal single-module nonribosomal peptide synthetase in terpene-amino acid meroterpenoid biosynthesis.Journal of industrial microbiology & biotechnology · 2023Article
- Total Heterologous Biosynthesis of Fungal Natural Products inJournal of natural products · 2022Review
- Enzymatic Synthesis of Diverse Heterocycles by a Noncanonical Nonribosomal Peptide Synthetase.ACS chemical biology · 2021Article
- Lentzeacins A-E, New Bacterial-Derived 2,5- and 2,6-Disubstituted Pyrazines from a BGC-Rich Soil BacteriumMolecules (Basel, Switzerland) · 2021Article
- Secondary metabolite biosynthetic diversity in the fungal familyStudies in mycology · 2021Article
- Ideality in Context: Motivations for Total Synthesis.Accounts of chemical research · 2021Article
- Biosynthesis of the Immunosuppressant (-)-FR901483.Journal of the American Chemical Society · 2021Article
- Discovery and biosynthesis of guanipiperazine from a NRPS-like pathway.Chemical science · 2021Article
- Piperazine ring formation by a single-module NRPS and cleavage by an α-KG-dependent nonheme iron dioxygenase in brasiliamide biosynthesis.Applied microbiology and biotechnology · 2020Article
- Complete Stereoinversion of l-Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase.Journal of the American Chemical Society · 2019Article
- Structure-guided function discovery of an NRPS-like glycine betaine reductase for choline biosynthesis in fungi.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Enantioselective synthesis ofChemical science · 2019Article
- Concise Total Synthesis of Herqulines B and C.Journal of the American Chemical Society · 2019Article
- Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions.Biochemistry · 2018Review
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Nature synthesizes many strained natural products that have diverse biological activities. Uncovering these biosynthetic pathways may lead to biomimetic strategies for organic synthesis of such compounds. In this work, we elucidated the concise biosynthetic pathway of herquline A, a highly strained and reduced fungal piperazine alkaloid. The pathway builds on a nonribosomal peptide synthetase derived dityrosine piperazine intermediate. Following enzymatic reduction of the P450-cross-linked dicyclohexadienone, N-methylation of the piperazine serves as a trigger that leads to a cascade of stereoselective and nonenzymatic transformations. Computational analysis of key steps in the pathway rationalizes the observed reactivities.
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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.