Confirmation of the absolute stereochemistry of a polymeric natural product from a macroalgal endophyte
Loading...
Date
2018
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
University of New Brunswick
Abstract
The bioactive biopolymer, poly(3,5-dihydroxyhexanoic acid), was previously isolated from an unidentified fungal endophyte of the marine macroalga Scytosiphon lamentaria. Literature reports for this compound failed to provide adequate details about poly(3,5-dihydroxyhexanoic acid) to allow for its complete characterization, thus requiring additional methods to be employed to determine the absolute stereochemistry of poly(3,5-dihydroxyhexanoic acid). Saponification of poly(3,5-dihydroxyhexanoic acid) yielded the lactone, 4-hydroxy-6-methyltetrahydro-2H-pyran-2-one. Nuclear magnetic resonance spectroscopy and polarimetry confirmed that the lactone was the 3R, 5R enantiomer, thus, the biopolymer isolated was confirmed to be poly(3R,5R-dihydroxyhexanoic acid).