Convergent synthesis of aminomethylene peptidomimetics

作者: Naila Assem , Andrei K Yudin

DOI: 10.1038/NPROT.2012.066

关键词:

摘要: This protocol describes a convergent synthesis of reduced amide bond peptidomimetics using thioacid-terminated peptides and aziridine-containing peptide conjugates. approach could be used to produce proteins with modified backbones. The conjugates are made readily available aziridine aldehydes. is demonstrated through the preparation long short fragments an aminomethylene group incorporated within them. transformation amenable bonds at cysteine alanine. procedure each component highlights ease peptidomimetics, takes about 3 d complete.

参考文章(25)
Luisa F. Carreño, Martha P. Alba, Yahson Varela, Manuel E. Patarroyo, José Manuel Lozano, A New Approach to Obtaining N α-t-Boc-Amino Acid Aldehydes from Asparagine and Glutamine for Reduced Amide Pseudopeptide Solid-Phase Synthesis Chemical Biology & Drug Design. ,vol. 78, pp. 603- 611 ,(2011) , 10.1111/J.1747-0285.2011.01182.X
Jan Weber, Pavel Majer, Jaroslav Litera, Jan Urban, Milan Souček, Jiřı́ Vondrášek, Jan Konvalinka, Petr Novek, Juraj Sedláček, Petr Štrop, Hans-Georg Kräusslich, Iva Pichová, None, POTENCY COMPARISON OF PEPTIDOMIMETIC INHIBITORS AGAINST HIV-1 AND HIV-2 PROTEINASES: DESIGN OF EQUIPOTENT LEAD COMPOUNDS Archives of Biochemistry and Biophysics. ,vol. 341, pp. 62- 69 ,(1997) , 10.1006/ABBI.1997.9945
Matthew G. Bursavich, Daniel H. Rich, Designing non-peptide peptidomimetics in the 21st century: inhibitors targeting conformational ensembles. Journal of Medicinal Chemistry. ,vol. 45, pp. 541- 558 ,(2002) , 10.1021/JM010425B
Mi-Sun Park, Hyun-Sik Oh, Hyeongjin Cho, Keun-Hyeung Lee, Microwave-assisted solid-phase synthesis of pseudopeptides containing reduced amide bond Tetrahedron Letters. ,vol. 48, pp. 1053- 1057 ,(2007) , 10.1016/J.TETLET.2006.11.151
Liang Z. Yan, Philip E. Dawson, Synthesis of Peptides and Proteins without Cysteine Residues by Native Chemical Ligation Combined with Desulfurization Journal of the American Chemical Society. ,vol. 123, pp. 526- 533 ,(2001) , 10.1021/JA003265M
Ryan Hili, Andrei K. Yudin, Readily available unprotected amino aldehydes. Journal of the American Chemical Society. ,vol. 128, pp. 14772- 14773 ,(2006) , 10.1021/JA065898S
M. Szelke, B. Leckie, A. Hallett, D. M. Jones, J. Sueiras, B. Atrash, A. F. Lever, Potent new inhibitors of human renin Nature. ,vol. 299, pp. 555- 557 ,(1982) , 10.1038/299555A0
Robert W. Dugger, John A. Ragan, David H. Brown Ripin, Survey of GMP Bulk Reactions Run in a Research Facility between 1985 and 2002 Organic Process Research & Development. ,vol. 9, pp. 253- 258 ,(2005) , 10.1021/OP050021J
Vincenzo Santagada, Francesco Frecentese, Ferdinando Fiorino, Donatella Cirillo, Elisa Perissutti, Beatrice Severino, Sara Terracciano, Giuseppe Caliendo, A Valuable Synthesis of Reduced Peptide Bond by Microwave Irradiation Qsar & Combinatorial Science. ,vol. 23, pp. 899- 901 ,(2004) , 10.1002/QSAR.200420037
Eriko Inokuchi, Ai Yamada, Kentaro Hozumi, Kenji Tomita, Shinya Oishi, Hiroaki Ohno, Motoyoshi Nomizu, Nobutaka Fujii, Design and synthesis of amidine-type peptide bond isosteres: application of nitrile oxide derivatives as active ester equivalents in peptide and peptidomimetics synthesis Organic and Biomolecular Chemistry. ,vol. 9, pp. 3421- 3427 ,(2011) , 10.1039/C0OB01193B