ArticleNature2017
Synergy of synthesis, computation and NMR reveals correct baulamycin structures.
Article in Nature, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 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.
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Who cites it
34 citing papers in PubMed.
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- Isolation of Verrucosins A-E from a MarineJournal of natural products · 2025Article
- Size-Programmable Matteson-Type Annulation: Construction of Spirocycles from Simple Cyclic Ketones.Angewandte Chemie (International ed. in English) · 2025Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A.Nature synthesis · 2025Article
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Mechanochemical Synthesis of α-halo Alkylboronic Esters.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- EFG-CS: Predicting chemical shifts from amino acid sequences with protein structure prediction using machine learning and deep learning models.Protein science : a publication of the Protein Society · 2024Article
- Synergy of Prediction Rule and Total Synthesis in Solving the Stereochemical Puzzle of Valactamides.Precision chemistry · 2024Article
- Base-mediated homologative rearrangement of nitrogen-oxygen bonds ofChemical science · 2023Article
- Ensemble determination by NMR data deconvolution.Nature reviews. Chemistry · 2023Review
- Posttranslational, site-directed photochemical fluorine editing of protein sidechains to probe residue oxidation state viaNature protocols · 2023Review
- Application of Lithiation-Borylation to the Total Synthesis of (-)-Rakicidin F.Organic letters · 2022Article
- Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters.Journal of the American Chemical Society · 2022Article
- In Situ Real-Time Quantitative Determination in Electrochemical Nuclear Magnetic Resonance Spectroscopy.Sensors (Basel, Switzerland) · 2021Article
- Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four-Membered Sulfur-Containing Cycles.Angewandte Chemie (International ed. in English) · 2021Article
- Real-time prediction ofChemical science · 2021Article
- Solubility Prediction from Molecular Properties and Analytical Data Using an In-phase Deep Neural Network (Ip-DNN).ACS omega · 2021Article
- Nuclear magnetic resonance free ligand conformations and atomic resolution dynamics.Magnetic resonance (Gottingen, Germany) · 2021Article
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7 authors.
Funding
Abstract
Small-molecule, biologically active natural products continue to be our most rewarding source of, and inspiration for, new medicines. Sometimes we happen upon such molecules in minute quantities in unique, difficult-to-reach, and often fleeting environments, perhaps never to be discovered again. In these cases, determining the structure of a molecule-including assigning its relative and absolute configurations-is paramount, enabling one to understand its biological activity. Molecules that comprise stereochemically complex acyclic and conformationally flexible carbon chains make such a task extremely challenging. The baulamycins (A and B) serve as a contemporary example. Isolated in small quantities and shown to have promising antimicrobial activity, the structure of the conformationally flexible molecules was determined largely through J-based configurational analysis, but has been found to be incorrect. Our subsequent campaign to identify the true structures of the baulamycins has revealed a powerful method for the rapid structural elucidation of such molecules. Specifically, the prediction of nuclear magnetic resonance (NMR) parameters through density functional theory-combined with an efficient sequence of boron-based synthetic transformations, which allowed an encoded (labelled) mixture of natural-product diastereomers to be prepared-enabled us rapidly to pinpoint and synthesize the correct structures.
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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.