Synthesis of and investigation of enantioselective properties of covalently linked vancomycin dimer

CHED 246

Matthew Oglesbee, oglesmd@millsaps.edu1, Keith Parsons1, Erin Redman1, Beth A. Baker, bakerba@millsaps.edu2, and Timothy J. Ward, wardtj@millsaps.edu2. (1) Chemistry Department, Millsaps College, 1701 North State St., Jackson, MS 39210, (2) Department of Chemistry, Millsaps College, Box 150306, 1701 North State Street, Jackson, MS 39210
The macrocyclic antibiotics contain functional groups and spatial arrangement that provide stereospecific interactions for chiral recognition. Previously, vancomycin monomer has been used to separate chiral compounds; however it is known that it is the assembly of dimers in solution when using native vancomycin that leads to enantioselectivity. In this work, vancomycin dimers attached via covalent bonding were used to separate chiral solutes. The separation using covalently linked dimers - synthesized by linking monomers via the primary amine on the sugar group - was compared with separation via self-assembled dimers of native vancomycin. Amino acids and NSAID's were used as target compounds. We noted significant differences in the separation effectiveness between the covalent dimers and the dimers of native vancomycin as well as in their physiochemical properties. A new synthesis is in progress in hopes to optimize the enantioselectivity of the covalently linked vancomycin dimer.
 

Undergraduate Research Poster Session: Analytical Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

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