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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
Stereospecific radical polymerization of N-triphenylmethylmethacrylamides leading to highly isotactic helical
Naohiro Hoshikawa1, Yuji Hotta, Yoshio Okamoto
1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.
Abstract:
N-Triphenylmethylmethacrylamide (TrMAM) and N-[di(4-butylphenyl)phenylmethyl]methacrylamide (DBuTrMAM) were polymerized using radical initiators. The polymer PTrMAM obtained from TrMAM was insoluble in the common solvents, but was dissolved in sulfuric acid to quantitatively give polymethacrylamide. The 1H NMR spectrum of PTrMAM in sulfuric acid-d2 indicated that the derived polymethacrylamide was nearly 100% isotactic. On the other hand, DBuTrMAM yielded the polymer PDBuTrMAM, which was soluble in THF and chloroform and whose NMR pattern in sulfuric acid-d2 was similar to that of PTrMAM. The polymerization of TrMAM and DBuTrMAM in an optically active solvent, (-)- or (+)-menthol, afforded the optically active polymers having a prevailing one-handed helical structure. The monomers were not solvolized in a methanol-chloroform mixture. TrMAM was not polymerized by anionic initiators.
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