Synthesis of aminoacylated dinucleotide, pdCpA-Baa, for ribosome-mediated biosynthesis of peptide sequence including Bucky amino acid (Baa)

ORGN 602

Amanda Strom, astrom@rice.edu, Department of Chemistry, Rice University, 6100 Main St, 410 Dell Butcher Hall, Houston, TX 77005 and Andrew R. Barron, arb@rice.edu, Department of Chemistry, Smalley Institute for Nanoscale Science and Technology, Rice University, 6100 Main Street, Houston, TX 77005.
Solid phase peptide synthesis (SPPS) is the standard method of peptide synthesis and is necessary when incorporating unnatural amino acids to a peptide sequence. However, SPPS is limited by significant errors and low yield occurring in peptide sequences of more than 20-30 amino acid residues. For this reason we are exploring a ribosome-mediated biosynthetic pathway which will incorporate the synthetic bucky-amino acid (Baa) to a peptide sequence. Initially, the hybrid dinucleotide pdCpA was chemically synthesized and aminoacylated with the synthetic bucky-amino acid. Misacylation is used to ligate pdCpA-Baa to a truncated suppressor tRNACUA(-CA) to make a chemically aminoacylated suppressor tRNA capable of translation. This process attempts to afford site-specific incorporation of a synthetic amino acid to a peptide sequence through ribosome-mediated biosynthesis of a synthetic peptide including bucky-amino acid in the sequence.
 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006