Wehner, Mark; Schrader, Thomas; Finocchiaro, Paolo; Failla, Salvatore; Consiglio, Giuseppe:

A Chiral Sensor for Arginine and Lysine.

In: Organic letters (Org.Lett.), Jg. 2 (2000) ; Nr. 5, S. 605-608
ISSN: 1523-7060
Zeitschriftenaufsatz / Fach: Chemie
We provide access to a new class of C1- or C2-sym. host mols. (I) and (II) based on a spirobisindane skeleton. Whereas I is selective for short, rigid diamines, II prefers longer a,w-dications. Of all the amino acid Me esters, only those of lysine and arginine with the correct distance between their cationic groups form strong 1:1 complexes in DMSO with II. NMR titrns. reveal high assocn. consts. as well as discrimination between the enantiomers of lysine and arginine.