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STRUCTURE/PEPTOIDS

Polymers are among the most important materials in modern society. Yet, when synthetic polymeric materials are compared to those found in biological organisms, they appear extremely limited in their applications. The major problem is that traditional synthetic polymer chemistry lacks one powerful capability that biological organisms have: the ability to precisely control the monomer sequence. Biopolymers (DNA, RNA, proteins, and some carbohydrates) are synthesized with specific monomer sequences. Information is encoded in the monomer sequence which specifies the unique fold and function of the molecule.

Design and synthesis of a new class of polymers, the "peptoids", has been initiated to address this problem. Peptoids are N-substituted polyglycine chains. A variety of designed or protein-like side chains can be attached sequence-specifically at the amide nitrogens along the molecule (rather than the C-alpha positions, like in proteins). Thus, on paper, peptoids resemble proteins. In three dimensions, however, their structures can be very different from protein structures and provide an interesting application and test for modern molecular modeling techniques. In collaboration with other groups, we are involved in the theoretical as well as the experimental research on peptoids.

References:

Burkoth TS, Beausoleil E, Kaur S, Tang D, Cohen FE, Zuckermann RN. (2002) Toward the synthesis of artificial proteins. The discovery of an amphiphilic helical peptoid assembly. Chem Biol 2002, 9: 647-654. [PDF]