Stereoselective synthesis and structural elucidation of dicarba peptides

Ellen C Gleeson, Zhen J Wang, Samuel D Robinson, Sandeep Chhabra, Christopher A MacRaild, W Roy Jackson, Raymond S Norton, Andrea J Robinson

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Abstract

A facile stereoselective synthesis of cis and trans unsaturated dicarba peptides has been established using preformed diaminosuberic acid derivatives as bridging units. In addition, characteristic spectral differences in the 13C-NMR spectra of the cis- and trans-isomers show that the chemical shift of carbons in the Δ4,5-diaminosuberic acid residue can be used to assign stereochemistry in unsaturated dicarba peptides formed from ring closing metathesis of linear peptide sequences.

Original languageEnglish
Pages (from-to)4446-4449
Number of pages4
JournalChemical Communications
Volume52
Issue number24
DOIs
Publication statusPublished - 2016

Cite this

Gleeson, E. C., Wang, Z. J., Robinson, S. D., Chhabra, S., MacRaild, C. A., Jackson, W. R., Norton, R. S., & Robinson, A. J. (2016). Stereoselective synthesis and structural elucidation of dicarba peptides. Chemical Communications, 52(24), 4446-4449. https://doi.org/10.1039/c5cc10540d