Synthesis of semirubins having phosphonic and sulfonic acid moieties

ORGN 373

Suchitra Datta, dattas@unr.nevada.edu and David A. Lightner. Department of Chemistry, University of Nevada, 1664 North Virginia Street, MS-216, Reno, NV 89557
[6]-Semirubin is dipyrrinone model for one-half of bilirubin, the yellow-orange neurotoxic pigment of jaundice. It is found to engage in intramolecular hydrogen bonding, between the carboxylic acid and the dipyrrinone lactam and pyrrole. Carboxylic acid and dipyrrinone moieties form a strongly attractive complementary hydrogen bonding pair. Although the carboxylic acid groups appears to be a perfect match for a dipyrrinone receptor, we have extended our study of hydrogen bonding to new [6]-semirubin analogs with CO2H group replaced by PO3H2 and SO3H. Their synthesis and hydrogen bonding studies will be presented.
 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008