ArticleJournal of natural products2012
Case study of empirical and computational chemical shift analyses: reassignment of the relative configuration of phomopsichalasin to that of diaporthichalasin.
Article in Journal of natural products, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 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
11 citing papers in PubMed.
- Improving the accuracy ofBeilstein journal of organic chemistry · 2023Article
- Progress in the Chemistry of Cytochalasans.Progress in the chemistry of organic natural products · 2021Article
- Oxygenated Theonellastrols: Interpretation of Unusual Chemical Behaviors Using Quantum Mechanical Calculations and Stereochemical Reassignment of 7Marine drugs · 2020Article
- Altercrasins A⁻E, Decalin Derivatives, from a Sea-Urchin-DerivedMarine drugs · 2019Article
- An automated framework for NMR chemical shift calculations of small organic molecules.Journal of cheminformatics · 2018Article
- Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical-Shift Analysis: Insights into their Mechanism of Action.Angewandte Chemie (International ed. in English) · 2015Article
- Isolation and Total Synthesis of Stolonines A-C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera.Marine drugs · 2015Article
- A guide to small-molecule structure assignment through computation of (¹H and ¹³C) NMR chemical shifts.Nature protocols · 2014Article
- Analysis of seven-membered lactones by computational NMR methods: proton NMR chemical shift data are more discriminating than carbon.The Journal of organic chemistry · 2014Article
- Structure reassignment of laurefurenynes A and B by computation and total synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Navigating the fungal polyketide chemical space: from genes to molecules.The Journal of organic chemistry · 2012Article
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.
Funding
Abstract
Phomopsichalasin was isolated and assigned structure 1 over 15 years ago. Analysis of its proton NMR data led us to hypothesize that not all aspects of the relative configuration of this structure were correct. We have used both empirical and computational methods to propose an alternative structure. Diaporthichalasin was reported several years ago, and its structure was assigned as 7, a diastereomer of structure 1, and confirmed by a single-crystal X-ray study. We have shown that diaporthichalasin and phomopsichalasin are identical; that is, both have structure 7. Additional aspects of NMR interpretation that provide guidance for avoiding some of the pitfalls that can lead to incorrect structure assignments are discussed. These recommendations/reminders include (i) the use of complementary solvents for acquiring NMR data that break accidental chemical shift degeneracy, (ii) the importance of assigning coupling constants as extensively as possible, and (iii) exercising caution when interpreting correlations in 2D spectra where overlapping resonances are involved.
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.