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Total synthesis of the proposed structure of talarolide A

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 16, Issue: 29, Page: 5286-5293
2018
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Article Description

The proposed structure of talarolide A, a cycloheptapeptide featuring a hydroxamate moiety within the peptide backbone, was successfully synthesized. An initial attempt to synthesize a linear peptide precursor containing a C-terminal N-benzyloxy glycine residue was problematic due to an unreported on-resin reduction of N-benzyloxy glycine to glycine. After repositioning the peptide cyclization point, a new linear peptide sequence was successfully prepared using Fmoc-solid-phase peptide synthesis. Subsequent solution-phase cyclization and removal of protecting groups furnished the synthetic talarolide A in good yield. Despite the mismatch of the NMR data between the synthetic talarolide A and the natural product, a detailed structural analysis using 2D NMR spectroscopy, together with re-synthesis of the same synthetic material using two additional cyclization sites, confirmed that our synthetic product has the reported structure of talarolide A.

Bibliographic Details

Zhang, Shengping; De Leon Rodriguez, Luis M; Huang, Renjie; Leung, Ivanhoe K H; Harris, Paul W R; Brimble, Margaret A

Royal Society of Chemistry (RSC)

Biochemistry, Genetics and Molecular Biology; Chemistry

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