Rapid Multistep Synthesis of a Bioactive Peptidomimetic Oligomer for the Undergraduate Laboratory.

作者: Yeliz Utku , Abhinav Rohatgi , Barney Yoo , Kent Kirshenbaum , Ronald N. Zuckermann

DOI: 10.1021/ED100202F

关键词:

摘要: Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive “peptoid” trimer. The six-step protocol is conducted on solid-phase resin, enabling to be performed by undergraduate organic chemistry students. This lab was successfully completed within one 4-h session second-year procedures relatively inexpensive and versatile, modifications generate variety oligomer sequences from commercially available reagents including bromoacetic acid diverse set primary amines.

参考文章(16)
Richard J. Simmonds, The synthesis of an amino acid derivative and spectroscopic monitoring of dipeptide formation Journal of Chemical Education. ,vol. 64, pp. 966- ,(1987) , 10.1021/ED064P966
Richard A. Blatchly, Timothy R. Allen, Dirk T. Bergstrom, Yuji Shinozaki, Microscale synthesis and analysis of a dipeptide Journal of Chemical Education. ,vol. 66, pp. 965- ,(1989) , 10.1021/ED066P965
Neel H. Shah, Glenn L. Butterfoss, Khanh Nguyen, Barney Yoo, Richard Bonneau, Dallas L. Rabenstein, Kent Kirshenbaum, Oligo(N-aryl glycines): A New Twist on Structured Peptoids Journal of the American Chemical Society. ,vol. 130, pp. 16622- 16632 ,(2008) , 10.1021/JA804580N
Nir Qvit, Yaniv Barda, Chaim Gilon, Deborah E. Shalev, A Laboratory Preparation of Aspartame Analogs Using Simultaneous Multiple Parallel Synthesis Methodology. Journal of Chemical Education. ,vol. 84, pp. 1988- 1991 ,(2007) , 10.1021/ED084P1988
Barney Yoo, Kent Kirshenbaum, Peptoid architectures: elaboration, actuation, and application Current Opinion in Chemical Biology. ,vol. 12, pp. 714- 721 ,(2008) , 10.1016/J.CBPA.2008.08.015
Susan M. Miller, Reyna J. Simon, Simon Ng, Ronald N. Zuckermann, Janice M. Kerr, Walter H. Moos, Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers Drug Development Research. ,vol. 35, pp. 20- 32 ,(1995) , 10.1002/DDR.430350105
Dennis G. Peters, Chang Ji, A Multistep Synthesis for an Advanced Undergraduate Organic Chemistry Laboratory Journal of Chemical Education. ,vol. 83, pp. 290- 291 ,(2006) , 10.1021/ED083P290
Cindy W Wu, Shannon L Seurynck, Ka Yee C Lee, Annelise E Barron, Helical peptoid mimics of lung surfactant protein C. Chemistry & Biology. ,vol. 10, pp. 1057- 1063 ,(2003) , 10.1016/J.CHEMBIOL.2003.10.008
Ray Bakhtiar, Steven A. Hofstadler, Richard D. Smith, Electrospray Ionization Mass Spectrometry: Part II: Applications in Characterization of Peptides and Proteins Journal of Chemical Education. ,vol. 73, ,(1996) , 10.1021/ED073PA118
Benjamin C. Gorske, Sarah A. Jewell, Emily J. Guerard, Helen E. Blackwell, Expedient synthesis and design strategies for new peptoid construction. Organic Letters. ,vol. 7, pp. 1521- 1524 ,(2005) , 10.1021/OL0502984