Synthesis of Fluorogenic Dye MaP655-Halo

The fluorogenic dye MaP655-Halo was synthesized as described previously (where the fluorogenic dye was initially named “Probe 29”)^{29 (link)}, stored at –20 °C in anhydrous dimethyl sulfoxide (DMSO, Sigma-Aldrich), and diluted in water (+/− DNA) to a 10-fold stock solution just before the expression experiments were started. Briefly, MaP655-Halo was synthesized upon protection of the 6-carboxy group of 6-carboxy silicon rhodamine using allyl bromide in the presence of Et₃N and K₂CO₃. Subsequently, the acyl chloride was formed by means of POCl₃ followed by nucleophilic acyl substitution with 3,5-difluorobenzenesulfonamide. Deprotection of the allyl ester using Pd(PPh₃)₄ and 1,3-dimethylbarbituric acid as well as coupling of the chloroalkane ligand to the 6-carboxy group by means of PyBOP and DIPEA yielded MaP655-Halo.

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Greiss F., Lardon N., Schütz L., Barak Y., Daube S.S., Weinhold E., Noireaux V, & Bar-Ziv R. (2024). A genetic circuit on a single DNA molecule as an autonomous dissipative nanodevice. Nature Communications, 15, 883.

Publication 2024

DMSO

Corresponding Organization : Weizmann Institute of Science

Other organizations : Max Planck Institute for Medical Research, RWTH Aachen University, University of Minnesota

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Variable analysis

independent variables

Protection of the 6-carboxy group of 6-carboxy silicon rhodamine using allyl bromide in the presence of Et3N and K2CO3
Formation of the acyl chloride by means of POCl3
Nucleophilic acyl substitution with 3,5-difluorobenzenesulfonamide
Deprotection of the allyl ester using Pd(PPh3)4 and 1,3-dimethylbarbituric acid
Coupling of the chloroalkane ligand to the 6-carboxy group by means of PyBOP and DIPEA

dependent variables

Synthesis of the fluorogenic dye MaP655-Halo

control variables

Stored at -20 °C in anhydrous dimethyl sulfoxide (DMSO, Sigma-Aldrich)
Diluted in water (+/- DNA) to a 10-fold stock solution just before the expression experiments were started

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