Absolute Configurations of Naturally Occurring [5]- and [3]-Ladderanoic Acids: Isolation, Chiroptical Spectroscopy, and Crystallography.

Raghavan V, Johnson JL, Stec DF, Song B, Zajac G, Baranska M, Harris CM, Schley ND, Polavarapu PL, Harris TM
J Nat Prod. 2018 81 (12): 2654-2666

PMID: 30562024 · DOI:10.1021/acs.jnatprod.8b00458

We have isolated mixtures of [5]- and [3]-ladderanoic acids 1a and 2a from the biomass of an anammox bioreactor and have separated the acids and their phenacyl esters for the first time by HPLC. The absolute configurations of the naturally occurring acids and their phenacyl esters are assigned as R at the site of side-chain attachment by comparison of experimental specific rotations with corresponding values predicted using quantum chemical (QC) methods. The absolute configurations for 1a and 2a were independently verified by comparison of experimental Raman optical activity spectra with corresponding spectra predicted using QC methods. The configurational assignments of 1a and 2a and of the phenacyl ester of 1a were also confirmed by X-ray crystallography.

MeSH Terms (10)

Biomass Bioreactors Circular Dichroism Crystallography, X-Ray Esters Lipids Molecular Conformation Molecular Structure Spectrum Analysis, Raman Stereoisomerism

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