Nanometer-scale, water-soluble macrocyclic receptors from iota-peptides

ORGN 269

Sang-Woo Kang, University of California, Irvine and James S. Nowick, jsnowick@uci.edu, Department of Chemistry, University of California, Irvine, 4126 Natural Sciences 1, Irvine, CA 92697-2025.
This paper introduces a new class of nanometer-sized, water-soluble macrocycles from the iota-amino acid aminodiphenylmethanecarboxylic acid (Adc). The functionalized variant AdcK, which has a lysine-like side chain for water solubility, is synthesized on a multigram scale by means of the Suzuki reaction. The macrocyclic tetramer cyclo(AdcK)4 is obtained by solid-phase synthesis of linear tetramer H-(AdcK(Boc))4-OH, followed by macrocyclization, deprotection, and RP-HPLC purification. 1H NMR Job plot and titration experiments show that cyclo(AdcK)4 forms a strong 1:1 complex (K=10000 M-1) with sodium cholate at tenth-millimolar concentrations. Current studies focus on the preparation of macrocyclic Adc tetramers bearing a series of different substituents in sequence. The ability to present a series of different substituents makes these macrocyclic Adc structures unique and valuable, as sequence cannot be easily achieved in cyclodextrins, calixarenes, porphyrins, and other important macrocycles.

 

Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006