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Issue 24, 2016
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Stereoselective synthesis and structural elucidation of dicarba peptides

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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.

Graphical abstract: Stereoselective synthesis and structural elucidation of dicarba peptides

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Publication details

The article was received on 24 Dec 2015, accepted on 10 Feb 2016 and first published on 10 Feb 2016


Article type: Communication
DOI: 10.1039/C5CC10540D
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Chem. Commun., 2016,52, 4446-4449

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    Stereoselective synthesis and structural elucidation of dicarba peptides

    E. C. Gleeson, Z. J. Wang, S. D. Robinson, S. Chhabra, C. A. MacRaild, W. R. Jackson, R. S. Norton and A. J. Robinson, Chem. Commun., 2016, 52, 4446
    DOI: 10.1039/C5CC10540D

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