Synthesis of a sensitive and selective potassium-sensing fluoroionophore.
An efficient synthesis is reported that delivers in 5 steps and 52% overall yield a new structurally simplified fluorescent K(+) sensor with improved K(+) sensitivity and selectivity over existing K(+) sensors. The synthesis procedure utilizes a new template-directed oxidative C-N bond-forming macrocyclization reaction and reports new approaches to Pd(0), Sandmeyer-like and metal-free aminoarylations, as well as organotitanium additions to vinylogous sulfonates.
Department of Medicine, Cardiovascular Research Institute, University of California, San Francisco, California, USA.
Richard D
RD
Carpenter
A S
AS
Verkman
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007476:Ionophores / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D008872:Microwaves; D015394:Molecular Structure; D011188:Potassium / Q000032:analysis*; D013237:Stereoisomerism
D000588:Amines; D005456:Fluorescent Dyes; D007476:Ionophores; D008024:Ligands; D011188:Potassium