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A Surprising Shift in the Biosynthesis of Marine Meroterpenoids
Author(s) -
Miles Zachary,
Deithelm Stefan,
George Jonathan,
Moore Bradley
Publication year - 2016
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.30.1_supplement.608.4
Subject(s) - halogenation , biosynthesis , chemistry , stereochemistry , enzyme , organic chemistry
A disproportionate number of halogenated natural products are derived from marine sources primarily due to the stark difference in elemental availability of halides in oceanic environments in comparison to their terrestrial cohorts. Vanadium‐dependent haloperoxidases (VHPOs), one class of enzymes that install these atoms, have historically been associated with non‐specific halogenation of compounds in various fungal and seaweed species. We previously characterized VHPOs from marine bacteria that control regiospecificity of halogenation to facilitate complex cyclizations in the biosynthesis of antimicrobial natural products. Recently, we observed a surprising chlorine‐mediated rearrangement reaction that accounts for the structures of two compounds from the merochlorin series of antibiotics that had yet to be explained. Ultimately, this observation appears to unexpectedly unify the biosyntheses of many related meroterpenoid natural products and expands the biochemical function of VHPOs. Support or Funding Information This work was supported by NIH grant AI047818 awarded to B.M.