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

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

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., ... Robinson, A. J. (2016). Stereoselective synthesis and structural elucidation of dicarba peptides. Chemical Communications, 52(24), 4446-4449. https://doi.org/10.1039/c5cc10540d
Gleeson, Ellen C ; Wang, Zhen J ; Robinson, Samuel D ; Chhabra, Sandeep ; MacRaild, Christopher A ; Jackson, W Roy ; Norton, Raymond S ; Robinson, Andrea J. / Stereoselective synthesis and structural elucidation of dicarba peptides. In: Chemical Communications. 2016 ; Vol. 52, No. 24. pp. 4446-4449.
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Gleeson, EC, Wang, ZJ, Robinson, SD, Chhabra, S, MacRaild, CA, Jackson, WR, Norton, RS & Robinson, AJ 2016, 'Stereoselective synthesis and structural elucidation of dicarba peptides', Chemical Communications, vol. 52, no. 24, pp. 4446-4449. https://doi.org/10.1039/c5cc10540d

Stereoselective synthesis and structural elucidation of dicarba peptides. / Gleeson, Ellen C; Wang, Zhen J; Robinson, Samuel D; Chhabra, Sandeep; MacRaild, Christopher A; Jackson, W Roy; Norton, Raymond S; Robinson, Andrea J.

In: Chemical Communications, Vol. 52, No. 24, 2016, p. 4446-4449.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Gleeson, Ellen C

AU - Wang, Zhen J

AU - Robinson, Samuel D

AU - Chhabra, Sandeep

AU - MacRaild, Christopher A

AU - Jackson, W Roy

AU - Norton, Raymond S

AU - Robinson, Andrea J

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Gleeson EC, Wang ZJ, Robinson SD, Chhabra S, MacRaild CA, Jackson WR et al. Stereoselective synthesis and structural elucidation of dicarba peptides. Chemical Communications. 2016;52(24):4446-4449. https://doi.org/10.1039/c5cc10540d