Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides

Iman Kavianinia; Sung-Hyun Yang; Harveen Kaur; Paul W. R. Harris; Renwick C. J. Dobson; Antony J. Fairbanks; Margaret A. Brimble

doi:10.1039/C7CC05025A

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Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides†

Iman Kavianinia,

^ab Sung-Hyun Yang,^a Harveen Kaur,

^a Paul W. R. Harris,^ab Renwick C. J. Dobson,

^bcd Antony J. Fairbanks

^e and Margaret A. Brimble

*^abf

Author affiliations

* Corresponding authors

^a School of Biological Sciences, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand

^b Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds St, Auckland, New Zealand

^c Biomolecular Interaction Centre and School of Biological Sciences University of Canterbury, Private Bag 4800, Christchurch, New Zealand

^d Department of Biochemistry and Molecular Biology, University of Melbourne, Parkville, Australia

^e Biomolecular Interaction Centre and Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand

^f School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand
E-mail: m.brimble@auckland.ac.nz

Abstract

Advanced lipid peroxidation end-products (ALEs) accumulate with ageing and oxidative stress-related diseases. Despite their potential therapeutic value, there are no suitably protected ALE building blocks reported in the literature to enable their site-specific incorporation into synthetic peptides. The synthesis of an Fmoc-protected ALE building block, N^∈-(3-methylpyridinium)lysine (MP-lysine) and its incorporation into collagen model peptides is reported.

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Article information

DOI: https://doi.org/10.1039/C7CC05025A
Article type: Communication
Submitted: 29 Jun 2017
Accepted: 06 Jul 2017
First published: 06 Jul 2017

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Chem. Commun., 2017,53, 8459-8462

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Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides

I. Kavianinia, S. Yang, H. Kaur, P. W. R. Harris, R. C. J. Dobson, A. J. Fairbanks and M. A. Brimble, Chem. Commun., 2017, 53, 8459 DOI: 10.1039/C7CC05025A

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Chemical Communications

Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides†

Abstract

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Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides

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