TY - JOUR
T1 - Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide
AU - Kise, Kenneth J.
AU - Bowler, Bruce E.
N1 - Funding Information:
We wish to thank John Stewart and Eunice York from the University of Colorado Health Sciences Center for their assistance with peptide synthesis, MALDI-TOF mass spectrometry, and for use of their polarimeter. Acknowledgment is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this work.
PY - 1998/9/18
Y1 - 1998/9/18
N2 - The synthesis of a bipyridyl amino acid, 2-amino-3-(4'-methyl-2,2'- bipyridin-4-yl) propanoic acid, is described. A short three step synthesis from commercially available 4,4'-dimethyl-2,2'-bipyridine provides the amino acid in 65% enantiomeric excess (ee). An enzyme-mediated chiral resolution increases the ee to 95% in two additional steps. The amino acid was incorporated into a 22 amino acid peptide composed predominantly of alanine. The peptide was found to be 88% α-helical in aqueous solution at 1°C by circular dichroism (CD) spectropolarimetry, indicating a high helical propensity for this amino acid. This amino acid can provide a means to incorporate a metal into structure-forming peptides.
AB - The synthesis of a bipyridyl amino acid, 2-amino-3-(4'-methyl-2,2'- bipyridin-4-yl) propanoic acid, is described. A short three step synthesis from commercially available 4,4'-dimethyl-2,2'-bipyridine provides the amino acid in 65% enantiomeric excess (ee). An enzyme-mediated chiral resolution increases the ee to 95% in two additional steps. The amino acid was incorporated into a 22 amino acid peptide composed predominantly of alanine. The peptide was found to be 88% α-helical in aqueous solution at 1°C by circular dichroism (CD) spectropolarimetry, indicating a high helical propensity for this amino acid. This amino acid can provide a means to incorporate a metal into structure-forming peptides.
UR - http://www.scopus.com/inward/record.url?scp=0032544781&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(98)00350-4
DO - 10.1016/S0957-4166(98)00350-4
M3 - Article
AN - SCOPUS:0032544781
SN - 0957-4166
VL - 9
SP - 3319
EP - 3324
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 18
ER -