PMID: 11902882Mar 21, 2002Paper

Influence of silaproline on peptide conformation and bioactivity

Journal of the American Chemical Society
F CavelierMichel Marraud

Abstract

The analogue gamma-(dimethylsila)-proline, denoted silaproline (Sip), was synthesized in both enantiomerically pure forms by diastereoselective alkylation of a chiral glycine equivalent with use of Schöllkopf's bis-lactim ether method. The effect of replacing a proline residue in model peptides by this new proline surrogate has been examined in the crystal state by X-ray diffraction and in solution by IR absorption and NMR techniques. Silaproline and proline-containing sequences exhibit very similar conformational properties. Silaproline was also substituted for proline in a neurotensin (8-13) analogue that retained biological activity and exhibited enhanced resistance to biodegradation.

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Citations

Oct 18, 2011·Amino Acids·C MartinF Cavelier
Oct 16, 2012·Journal of Medicinal Chemistry·Annaliese K Franz, Sean O Wilson
May 8, 2009·Chemical Society Reviews·Matthew MortensenCarsten Bolm
Feb 27, 2015·Amino Acids·Roberto FanelliFlorine Cavelier
Jan 12, 2008·Advanced Drug Delivery Reviews·Sílvia Pujals, Ernest Giralt
Mar 31, 2004·The Journal of Peptide Research : Official Journal of the American Peptide Society·F CavelierS Sagan
Dec 17, 2009·Journal of Peptide Science : an Official Publication of the European Peptide Society·Georgios A DalkasFlorine Cavelier
Sep 3, 2016·Journal of Medicinal Chemistry·Mark A T Blaskovich
Feb 12, 2005·Organic Letters·Guodong Liu, Scott McN Sieburth
Jul 27, 2017·Journal of the American Chemical Society·Huaquan FangZheng Huang
Mar 28, 2018·Journal of Peptide Science : an Official Publication of the European Peptide Society·Vladimir Kubyshkin, Nediljko Budisa
Aug 11, 2016·Organic & Biomolecular Chemistry·E CordeauC Enjalbal
Sep 13, 2014·Chemistry : a European Journal·Charlotte MartinFlorine Cavelier
Aug 18, 2018·Angewandte Chemie·Boris MinkovichYitzhak Apeloig
Jun 21, 2006·Journal of Peptide Science : an Official Publication of the European Peptide Society·Florine CavelierMichel Marraud
May 16, 2013·Organic & Biomolecular Chemistry·Rossella De MarcoLuca Gentilucci
Feb 10, 2012·Organic & Biomolecular Chemistry·Rossella De MarcoLuca Gentilucci
Jun 14, 2020·European Journal of Pharmacology·Pascal TétreaultPhilippe Sarret
Feb 27, 2020·The Journal of Organic Chemistry·Yassin M ElbatrawiJuan R Del Valle
Feb 20, 2021·Behavioural Brain Research·Mélanie VivancosPhilippe Sarret
Sep 6, 2020·Bioconjugate Chemistry·Roberto FanelliFlorine Cavelier
Apr 29, 2010·The Journal of Organic Chemistry·Dácil HernándezTroels Skrydstrup
Oct 19, 2017·Journal of Medicinal Chemistry·Remya Ramesh, D Srinivasa Reddy
May 16, 2018·Journal of the American Chemical Society·Scott J Barraza, Scott E Denmark
Jan 31, 2019·The Journal of Organic Chemistry·Raghunath ChowdhurySunil K Ghosh
Mar 6, 2019·Organic Letters·Toshimichi OhmuraMichinori Suginome
Jun 29, 2006·Journal of the American Chemical Society·Sílvia PujalsErnest Giralt
Jul 4, 2003·The Journal of Organic Chemistry·Claude CommandeurMax Malacria

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