Synthesis of an azido-tagged low affinity ratiometric calcium sensor

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Caldwell, Stuart T. and Cairns, Andrew G. and Olson, Marnie and Chalmers, Susan and Sandison, Mairi and Mullen, William and McCarron, John G. and Hartley, Richard C. (2015) Synthesis of an azido-tagged low affinity ratiometric calcium sensor. Tetrahedron, 71 (51). 9571–9578. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2015.10.052)

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Abstract

Changes in high localized concentrations of Ca2+ ions are fundamental to cell signalling. The synthesis of a dual excitation, ratiometric calcium ion sensor with a Kd of 90 μM, is described. It is tagged with an azido group for bioconjugation, and absorbs in the blue/green and emits in the red region of the visible spectrum with a large Stokes shift. The binding modulating nitro group is introduced to the BAPTA core prior to construction of a benzofuran-2-yl carboxaldehyde by an allylation-oxdiation-cyclization sequence, which is followed by condensation with an azido-tagged thiohydantoin. The thiohydantoin unit has to be protected with an acetoxymethyl (AM) caging group to allow CuAAC click reaction and incorporation of the KDEL peptide endoplasmic reticulum (ER) retention sequence.

ORCID iDs

Caldwell, Stuart T., Cairns, Andrew G., Olson, Marnie, Chalmers, Susan ORCID logoORCID: https://orcid.org/0000-0002-8073-7576, Sandison, Mairi ORCID logoORCID: https://orcid.org/0000-0003-1021-1461, Mullen, William, McCarron, John G. ORCID logoORCID: https://orcid.org/0000-0002-3302-3984 and Hartley, Richard C.;
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