Total synthesis of a peptide diatom sex pheromone bearing an unusual sulfated aspartic acid

30 May 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The peptide Sex Inducing Pheromone SIP+ bearing an unusual sulfated aspartic acid residue induces sexual reproduction in diatom populations. Herein, we report the first total synthesis of SIP+ using both a sulfated building block approach and a SPPS compatible late-stage sulfation strategy to assemble the natural product. The modular approaches provide concise routes to useful quantities of the natural product for future SAR investigations examining the role of SIP+ in diatom biology.

Keywords

Total synthesis
Sex Inducing Pheromone
SIP+
Peptide
Sulfate
Diatom
SPPS

Supplementary materials

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A description of experimental protocols and characterization data.
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