Synthesis of recognition components for fluorescent proteomimetics

ORGN 382

Emilia Vesper, mheagy@nmt.edu, Department of Chemistry, New Mexico Tech, 801 Leroy Avenue, Socorro, NM 87801 and Michael D Heagy, mheagy@nmt.edu, Department of Chemistry, New Mexico Institute of Mining & Technology, Jones Hall RM 259, Socorro, NM 87801.
As part of our continuing work with fluorescent proteomimetics a current focus has been on functionalizing 4,4'-biaryls. These compounds will be incorporated into our fluorescent platforms as functionalized ter-aryl systems. The synthetic plan involves using bromobenzaldehyde with commercially available grignard reagents as shown below. The resulting alcohol will then be reduced via sodium borohydride to give the necessary hydrocarbon proteomimetic. The penultimate step involves Suzuki coupling of the bromoarene with another functionalized aminobenzeneboronic acid.