Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

Chemical Science
Marcos San Segundo, Arkaitz Correa

Abstract

The development of useful synthetic tools to label amino acids within a peptide framework for the ultimate modification of proteins in a late-stage fashion is a challenging task of utmost importance within chemical biology. Herein, we report the first Pd-catalyzed C-H acylation of a collection of Tyr-containing peptides with aldehydes. This water-compatible tagging technique is distinguished by its site-specificity, scalability and full tolerance of sensitive functional groups. Remarkably, it provides straightforward access to a high number of oligopeptides with altered side-chain topology including mimetics of endomorphin-2 and neuromedin N, thus illustrating its promising perspectives toward the diversification of structurally complex peptides and chemical ligation.

References

Dec 9, 2004·Journal of the American Chemical Society·Neel S JoshiMatthew B Francis
Jan 26, 2006·Journal of the American Chemical Society·S David Tilley, Matthew B Francis
Oct 5, 2006·Journal of the American Chemical Society·Woo-Jin Yoo, Chao-Jun Li
May 22, 2007·Journal of Medicinal Chemistry·Nicolas BasseJoëlle Vidal
Dec 12, 2007·Bioconjugate Chemistry·Dante W Romanini, Matthew B Francis
May 24, 2008·Journal of the American Chemical Society·Jesse M McFarlandMatthew B Francis
Feb 13, 2009·Chemical Reviews·Arani Chanda, Valery V Fokin
Jan 14, 2010·Journal of the American Chemical Society·Hitoshi BanCarlos F Barbas
Oct 5, 2011·Journal of the American Chemical Society·Kristen L SeimMatthew B Francis
Apr 13, 2012·Journal of the American Chemical Society·Mathew W JonesDavid M Haddleton
Aug 25, 2012·Future Medicinal Chemistry·Fernando Albericio, Hendrik G Kruger
Mar 27, 2013·Chemical Society Reviews·Manoj B GawandeRajender S Varma
Sep 11, 2013·Chemistry : a European Journal·Wenbo Ma, Lutz Ackermann
Apr 1, 2014·Chemical Communications : Chem Comm·Jing WangAiwen Lei
Aug 22, 2014·Chemical Reviews·Anaïs F M Noisier, Margaret A Brimble
Dec 17, 2014·The Journal of Organic Chemistry·Alison E Metz, Marisa C Kozlowski
Mar 11, 2015·Accounts of Chemical Research·Olafs DaugulisLy Dieu Tran
Jul 3, 2015·Chemistry : a European Journal·Xiao-Feng Wu
Jan 23, 2016·Nature Chemistry·Nikolaus KrallGonçalo J L Bernardes
Dec 3, 2016·Angewandte Chemie·Anaïs F M NoisierFernando Albericio
Apr 7, 2017·Angewandte Chemie·Muhammad JbaraAshraf Brik
Jun 28, 2017·Biochemistry·Justine N deGruyterPhil S Baran
Jul 20, 2017·Bioorganic & Medicinal Chemistry·Jolene L Lau, Michael K Dunn
Jul 25, 2017·Journal of Medicinal Chemistry·Antoine HenninotJohn M Nuss
Feb 27, 2018·Phytochemistry·Craig A Schenck, Hiroshi A Maeda
Apr 16, 2018·Current Opinion in Chemical Biology·Lara R Malins
May 16, 2018·Journal of the American Chemical Society·Younong YuZhi-Cai Shi
May 22, 2018·Chemical Science·Naoko IchiishiShane W Krska
Jun 9, 2018·Angewandte Chemie·Wei WangLutz Ackermann
Jul 4, 2018·Angewandte Chemie·Wei WangLutz Ackermann
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Aug 1, 2018·Chemistry : a European Journal·Cecilia Bottecchia, Timothy Noël

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Citations

Jan 13, 2021·Chemistry : a European Journal·Paula Andrade-SampedroArkaitz Correa
Sep 4, 2021·Organic Letters·Iñaki UrruzunoArkaitz Correa

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Methods Mentioned

BETA
acylation
column chromatography

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