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

Abstract

<p>A combined computational and anisotropic NMR investigation defined likely configuration of phormidolide.</p>

Polyketide β-branching: diversity, mechanism and selectivity

“…It should be noted that an ambiguity in labelling of ECH 1 and ECH 2 domains was identied and analysis of the sequences deposited in genbank suggest that PhmO is in fact the ECH 1 domain and PhmN is the ECH 2 domain. Using chemical synthesis, computation and NMR analysis, the stereochemistry of phormidolide has also been reassigned by Ndukwe et al [117][118][119]…”

Computational 1H and 13C NMR of the trimeric monoterpenoid indole alkaloid strychnohexamine: Selected spectral updates

“…Philippe and coauthors described the isolation [19] and complete structural elucidation [19,20] of strychnohexamine by employing correlation spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), heteronuclear multiple quantum coherence (HMQC), heteronuclear single quantum coherence (HSQC), total correlation spectroscopy (TOCSY), and rotating-frame nuclear Overhauser effect spectroscopy (ROESY) NMR pulse techniques, which was the starting point of the present study. Strychnohexamine is indeed one of the largest natural products ever isolated from nature; however, much larger natural alkaloids are known, being exemplified here with maitotoxin 1 (1), [22] phormidolide A (2), [23] and palytoxin (3) shown, accordingly, in Figures 1-3.…”

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

“…Simultaneously, a reanalysis of the biosynthetic gene cluster suggested additional revisions in configuration were possibly required [ 70 ]. These findings stimulated a concerted computational and NMR-based re-investigation of phormidolide’s complex 3-dimensional structure, leading to a revision in several stereocenters ( 42 ) [ 71 ].…”