Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase

Meirong Jia, Terrence E. O'Brien, Yue Zhang, Justin Siegel, Dean J. Tantillo, Reuben J. Peters

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Sclareol synthase from Salvia sclarea (SsSS) naturally acts on 8α-hydroxy-copalyl diphosphate (1), stereoselectively adding water to produce (13R)-sclareol (2a), and similarly yields hydroxylated products with many-fold other such bicyclic diterpene precursors. Here, a key residue for this addition of water was identified. Strikingly, substitution with glutamine switches stereochemical outcome with 1, leading to the selective production of (13S)-sclareol (2b). Moreover, changes to the stereospecificity of water addition with the structurally closely related substrate copalyl diphosphate (4) could be accomplished with alternative substitutions. Thus, this approach is expected to provide biosynthetic access to both epimers of 13-hydroxylated derivatives of many-fold labdane-related diterpenes.

Original languageEnglish (US)
Pages (from-to)3133-3137
Number of pages5
JournalACS Catalysis
Volume8
Issue number4
DOIs
StatePublished - Apr 6 2018

ASJC Scopus subject areas

  • Catalysis

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    Jia, M., O'Brien, T. E., Zhang, Y., Siegel, J., Tantillo, D. J., & Peters, R. J. (2018). Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase. ACS Catalysis, 8(4), 3133-3137. https://doi.org/10.1021/acscatal.8b00121