Preprint Communication Version 1 This version is not peer-reviewed

Proposed “Biosynthesis” of Primarolides A and B from a Common 2-Formylbenzophenone Precursor

Version 1 : Received: 4 November 2019 / Approved: 6 November 2019 / Online: 6 November 2019 (02:53:57 CET)

How to cite: Schmalz, H. Proposed “Biosynthesis” of Primarolides A and B from a Common 2-Formylbenzophenone Precursor. Preprints 2019, 2019110051 (doi: 10.20944/preprints201911.0051.v1). Schmalz, H. Proposed “Biosynthesis” of Primarolides A and B from a Common 2-Formylbenzophenone Precursor. Preprints 2019, 2019110051 (doi: 10.20944/preprints201911.0051.v1).

Abstract

The structures of recently discovered primarolides A and B suggest their non-enzymatic formation from a common 2-formylbenzophenone precursor. This hypothesis is based on the experimentally proven facile conversion of pestalone (also a 2-formyl-benzophenone) either into the isomeric lactone pestalalactone or the structurally related isoindolinone pestalachloride A. In a related fashion, the racemic isoindolinone natural product mariline A is supposed to biosynthetically originate from the corresponding keto-aldehyde and an aniline, as experimentally supported by model studies. Due to the close structural relationship with known systems, it appears highly probable that primarolides A and B were generated under the fermentation conditions from a massarinin-related 2-formylbenzophenone (proprimarolide) by reaction either with aniline or a nucleophilic catalyst, respectively. Suberoylanilide hydroxamic acid (SAHA), used as an additive during the fermentation, is supposed to act both as a source of aniline and as a nucleophilic catalyst.

Subject Areas

lactones; lactames; isoindolinones; non-enzymatic biosynthesis; benzophenones; polyketides; reactive natural products; saha; aniline; hydroxamic acids

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