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peptoid
Peptoids, or poly-''N''-substituted glycines, are a class of peptidomimetics whose side chains are appended to the nitrogen atom of the peptide backbone, rather than to the α-carbons (as they are in amino acids).
==Chemical structure and synthesis==
In peptoids the side chain is connected to the nitrogen of the peptide backbone, instead of the α-carbon as in peptides. Notably, peptoids lack the amide hydrogen which is responsible for many of the Secondary structure elements in peptides and proteins. Peptoids were first invented by Reyna J. Simon, Paul Bartlett and Daniel V. Santi to mimic protein/peptide products to aid in the discovery of protease-stable small molecule drugs.〔Reyna J Simon, Robert S Kania, Ronald N Zuckermann, Verena D Huebner, David A Jewell, Steven Banville, Simon Ng, Liang Wang, Steven Rosenberg, Charles K Marlowe, David C Spellmeyer, Ryoying Tan, Alan D Frankel, Daniel V Santi, Fred E Cohen, and Paul A Bartlett, "Peptoids: a modular approach to drug discovery" Proceedings of the National Academy of Sciences USA, (1992), 89(20), 9367-9371〕〔Reyna J Simon, Paul A Bartlett, Daniel V Santi, "Peptoid Mixtures", US Patent 5,811,387, Sept 22, 1998〕
Following the sub-monomer protocol originally created by Ron Zuckermann,〔Ronald N. Zuckermann, Janice M. Kerr, Stephen B. H. Kent, Walter H. Moos, ''Efficient method for the preparation of peptoids (glycines) ) by submonomer solid-phase synthesis'' Journal of the American Chemical Society, (1992), 114(26), 10646-10647 〕 each residue is installed in two steps: acylation and displacement. In the acylation step a haloacetic acid, typically bromoacetic acid activated by diisopropylcarbodiimide reacts with the amine of the previous residue. In the displacement step (a classical SN2 reaction), an amine displaces the halide to form the ''N''-substituted glycine residue. The submonomer approach allows the use of any commercially available or synthetically accessible amine with great potential for Combinatorial chemistry.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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