Literature DB >> 32520016

Synergism of anisotropic and computational NMR methods reveals the likely configuration of phormidolide A.

Ikenna E Ndukwe1, Xiao Wang2, Nelson Y S Lam3, Kristaps Ermanis3, Kelsey L Alexander4, Matthew J Bertin5, Gary E Martin6, Garrett Muir7, Ian Paterson3, Robert Britton7, Jonathan M Goodman3, Eric J N Helfrich8, Jörn Piel8, William H Gerwick9, R Thomas Williamson10.   

Abstract

Characterization of the complex molecular scaffold of the marine polyketide natural product phormidolide A represents a challenge that has persisted for nearly two decades. In light of discordant results arising from recent synthetic and biosynthetic reports, a rigorous study of the configuration of phormidolide A was necessary. This report outlines a synergistic effort employing computational and anisotropic NMR investigation, that provided orthogonal confirmation of the reassigned side chain, as well as supporting a further correction of the C7 stereocenter.

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Year:  2020        PMID: 32520016      PMCID: PMC7436192          DOI: 10.1039/d0cc03055d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  27 in total

1.  Total Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure-Activity Relationship Study.

Authors:  Yuma Wakamiya; Makoto Ebine; Nobuaki Matsumori; Tohru Oishi
Journal:  J Am Chem Soc       Date:  2020-02-06       Impact factor: 15.419

2.  The optimal DFT approach in DP4 NMR structure analysis - pushing the limits of relative configuration elucidation.

Authors:  Kristaps Ermanis; Kevin E B Parkes; Tatiana Agback; Jonathan M Goodman
Journal:  Org Biomol Chem       Date:  2019-05-31       Impact factor: 3.876

3.  Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium Phormidium sp.

Authors:  R Thomas Williamson; Anna Boulanger; Alexandra Vulpanovici; Mary A Roberts; William H Gerwick
Journal:  J Org Chem       Date:  2002-11-15       Impact factor: 4.354

4.  Order matrix analysis of residual dipolar couplings using singular value decomposition.

Authors:  J A Losonczi; M Andrec; M W Fischer; J H Prestegard
Journal:  J Magn Reson       Date:  1999-06       Impact factor: 2.229

5.  Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors:  Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

6.  Unequivocal determination of complex molecular structures using anisotropic NMR measurements.

Authors:  Yizhou Liu; Josep Saurí; Emily Mevers; Mark W Peczuh; Henk Hiemstra; Jon Clardy; Gary E Martin; R Thomas Williamson
Journal:  Science       Date:  2017-04-07       Impact factor: 47.728

7.  The Phormidolide Biosynthetic Gene Cluster: A trans-AT PKS Pathway Encoding a Toxic Macrocyclic Polyketide.

Authors:  Matthew J Bertin; Alexandra Vulpanovici; Emily A Monroe; Anton Korobeynikov; David H Sherman; Lena Gerwick; William H Gerwick
Journal:  Chembiochem       Date:  2015-12-23       Impact factor: 3.164

8.  Thermoresponsive Alignment Media in NMR Spectroscopy: Helix Reversal of a Copolyaspartate at Ambient Temperatures.

Authors:  Mira Schwab; Volker Schmidts; Christina M Thiele
Journal:  Chemistry       Date:  2018-08-30       Impact factor: 5.236

9.  Automated structure prediction of trans-acyltransferase polyketide synthase products.

Authors:  Eric J N Helfrich; Reiko Ueoka; Alon Dolev; Michael Rust; Roy A Meoded; Agneya Bhushan; Gianmaria Califano; Rodrigo Costa; Muriel Gugger; Christoph Steinbeck; Pablo Moreno; Jörn Piel
Journal:  Nat Chem Biol       Date:  2019-07-15       Impact factor: 15.040

10.  Enhanced measurement of residual chemical shift anisotropy for small molecule structure elucidation.

Authors:  Yizhou Liu; Ryan D Cohen; Kirk R Gustafson; Gary E Martin; R Thomas Williamson
Journal:  Chem Commun (Camb)       Date:  2018-04-24       Impact factor: 6.222

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  5 in total

Review 1.  The Chemistry, Biochemistry and Pharmacology of Marine Natural Products from Leptolyngbya, a Chemically Endowed Genus of Cyanobacteria.

Authors:  Yueying Li; C Benjamin Naman; Kelsey L Alexander; Huashi Guan; William H Gerwick
Journal:  Mar Drugs       Date:  2020-10-06       Impact factor: 5.118

2.  The Natural Products Atlas 2.0: a database of microbially-derived natural products.

Authors:  Jeffrey A van Santen; Ella F Poynton; Dasha Iskakova; Emily McMann; Tyler A Alsup; Trevor N Clark; Claire H Fergusson; David P Fewer; Alison H Hughes; Caitlin A McCadden; Jonathan Parra; Sylvia Soldatou; Jeffrey D Rudolf; Elisabeth M-L Janssen; Katherine R Duncan; Roger G Linington
Journal:  Nucleic Acids Res       Date:  2022-01-07       Impact factor: 16.971

Review 3.  The Tetrahydrofuran Motif in Polyketide Marine Drugs.

Authors:  Laura Fernández-Peña; Carlos Díez-Poza; Paula González-Andrés; Asunción Barbero
Journal:  Mar Drugs       Date:  2022-02-03       Impact factor: 5.118

4.  The DP5 probability, quantification and visualisation of structural uncertainty in single molecules.

Authors:  Alexander Howarth; Jonathan M Goodman
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

5.  Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements.

Authors:  Ikenna E Ndukwe; Yu-Hong Lam; Sunil K Pandey; Bengt E Haug; Annette Bayer; Edward C Sherer; Kirill A Blinov; R Thomas Williamson; Johan Isaksson; Mikhail Reibarkh; Yizhou Liu; Gary E Martin
Journal:  Chem Sci       Date:  2020-09-21       Impact factor: 9.825

  5 in total

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