An unnatural biopolymer.
A highly efficient method has been developed for the solid-phase synthesis of an "unnatural biopolymer" consisting of chiral aminocarbonate monomers linked via a carbamate backbone. Oligocarbamates were synthesized from N-protected p-nitrophenyl carbonate monomers, substituted with a variety of side chains, with greater than 99 percent overall coupling efficiencies per step. A spatially defined library of oligocarbamates was generated by using photochemical methods and screened for binding affinity to a monoclonal antibody. A number of high-affinity ligands were then synthesized and analyzed in solution with respect to their inhibition concentration values, water/octanol partitioning coefficients, and proteolytic stability. These and other unnatural polymers may provide new frameworks for drug development and for testing theories of protein and peptide folding and structure.
Cho
C Y
CY
Department of Chemistry, University of California, Berkeley 94720.
Moran
E J
EJ
Cherry
S R
SR
Stephans
J C
JC
Fodor
S P
SP
Adams
C L
CL
Sundaram
A
A
Jacobs
J W
JW
Schultz
P G
PG
D000595:Amino Acid Sequence; D000818:Animals; D000911:Antibodies, Monoclonal / Q000276:immunology; D001704:Biopolymers; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D000939:Epitopes; D051379:Mice; D008807:Mice, Inbred BALB C; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000737:chemistry
D000911:Antibodies, Monoclonal; D001704:Biopolymers; D002254:Carbonates; D000939:Epitopes; D009842:Oligopeptides