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

Vijay Raghavan, Jordan L. Johnson, Donald F. Stec, Bongkeun Song, Grzegorz Zajac, Malgorzata Baranska, Constance M. Harris, Nathan D. Schley, Prasad L. Polavarapu, Thomas M. Harris
Journal of natural products 2018 v.81 no.12 pp. 2654-2666
X-ray diffraction, anaerobic ammonium oxidation, biomass, bioreactors, crystallography, esters, high performance liquid chromatography, optical properties, quantum mechanics, spectroscopy
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.