A homobifunctional rhodamine for labeling proteins with defined orientations of a fluorophore

Bioconjugate Chemistry
J E CorrieV R Munasinghe

Abstract

The synthesis and characterization of a bifunctional rhodamine dye bearing 2-(iodoacetamido)ethyl substituents on the 3'- and 6'-nitrogen atoms is described. Aspects of the conversion of chloroacetamides to iodoacetamides are discussed, including a remarkably mild dehalogenation of an aromatic haloacetamide in the presence of NaI and camphorsulfonic acid. The bifunctional rhodamine has been designed for two-site, 1:1 labeling of proteins that contain two suitably disposed cysteine residues and is intended to constrain the orientation of the rhodamine absorption and emission dipoles in a predictable relationship to the protein structure.

Citations

Jun 27, 2002·Journal of Molecular Biology·Seth C HopkinsYale E Goldman
Dec 7, 2000·Progress in Biophysics and Molecular Biology·J N ForkeyY E Goldman
Dec 14, 2006·ACS Chemical Biology·Luke D LavisRonald T Raines
Apr 7, 2010·Nature Structural & Molecular Biology·Yujie SunYale E Goldman
Jul 23, 2009·Chemical Society Reviews·Mariana BeijaJosé M G Martinho
Feb 1, 2012·The Journal of General Physiology·John H LewisYale E Goldman
Jul 23, 2004·The Journal of Chemical Physics·Jose A B Ferreira, Silvia M B Costa
Mar 13, 2014·Proceedings of the National Academy of Sciences of the United States of America·Luca FusiMalcolm Irving
Nov 15, 2006·Proceedings of the National Academy of Sciences of the United States of America·Yin-Biao SunMalcolm Irving
Nov 19, 2008·The Journal of Physiology·Yin-Biao SunMalcolm Irving
Sep 6, 2015·Journal of Molecular and Cellular Cardiology·Ian M RobertsonBrian D Sykes
Jul 16, 2008·Biophysical Journal·Andrea C KnowlesMalcolm Irving
Oct 1, 2005·Protein Science : a Publication of the Protein Society·Lakmal Jayasinghe, Hagan Bayley
Dec 27, 2007·Molecular Cell·Yujie SunYale E Goldman
Mar 27, 2013·Biophysical Journal·John F BeausangYale E Goldman
Mar 15, 2015·American Journal of Physiology. Heart and Circulatory Physiology·D DuggalJ Borejdo
Nov 29, 2013·American Journal of Physiology. Regulatory, Integrative and Comparative Physiology·Divya DuggalJulian Borejdo
May 8, 2014·Organic & Biomolecular Chemistry·Michaela KotaskovaMark Helm
Apr 30, 2003·Molecular Cell·Roisean E FergusonMalcolm Irving
May 3, 2012·Cold Spring Harbor Protocols·John F BeausangYale E Goldman

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