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 varie...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 1993-09, Vol.261 (5126), p.1303-1305
Main Authors: Cho, Charles Y., Moran, Edmund J., Cherry, Sara R., Stephans, James C., Stephen P. A. Fodor, Adams, Cynthia L., Sundaram, Arathi, Jacobs, Jeffrey W., Schultz, Peter G.
Format: Article
Language:English
Subjects:
400201 - Chemical & Physicochemical Properties
AMINES
Amino Acid Sequence
Amino acids
Animals
Antibodies
Antibodies, Monoclonal - immunology
Applied sciences
Biochemistry
Biopolymers
CARBAMATES
CARBON COMPOUNDS
CARBONATES
Carbonates - chemical synthesis
Carbonates - chemistry
Carbonates - immunology
CARBONIC ACID DERIVATIVES
CARBOXYLIC ACID SALTS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
Epitopes
Exact sciences and technology
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Libraries
Ligands
Mice
Mice, Inbred BALB C
Miscellaneous
Molecular Sequence Data
Monomers
NITRO COMPOUNDS
Oligopeptides - chemistry
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
Physicochemistry of polymers
POLYMERIZATION
POLYMERS
Resins
SYNTHESIS
Synthetic biopolymers
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Summary: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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.7689747