Photoaffinity-Labeled Peptoids and Depsipeptides by Multicomponent Reactions

Abstract

Photoaffinity tags can be incorporated easily into peptoids and congeners by the Ugi and Passerini multicomponent reactions. Products related to photo-methionine and photo-leucine can be accomplished by diazirine-containing building blocks. The same protocols can be used to synthesize derivatives with benzophenone photo cross-linkers.

Key words

photo-methionine - photo-leucine - Ugi reaction - Passerini­ reaction - peptoids

References

• 1a Kawakami T. Murakami H. Suga H. J. Am. Chem. Soc.  2008,  130:  16861 
• 1b Masip I. Pérez-Payá E. Messeguer A. Comb. Chem. High Throughput Screening  2005,  8:  235 
• 1c Shah NH. Butterfoss GL. Nguyen K. Yoo B. Bonneau R. Rabenstein DL. Kirshenbaum K. J. Am. Chem. Soc.  2008,  130:  16622 
• 1d Zuckermann RN. Kodadek T. Curr. Opin. Mol. Ther.  2009,  11:  299 
• 2 Kwon YU. Kodadek T. J. Am. Chem. Soc.  2007,  129:  1508 
• 3 Domling A. Chem. Rev.  2006,  106:  17 ; and references cited therein
• 4 Fowler SA. Blackwell HE. Org. Biomol. Chem.  2009,  7:  1508 ; and references cited therein
• 5 Gorske BC. Stringer JR. Bastian BL. Blackwell HE. J. Am. Chem. Soc.  2009,  131:  16555 ; and references cited therein
• 6a Wang HX. Nakata E. Hamachi I. ChemBioChem  2009,  10:  2560 
• 6b Collet M. Lenger J. Jenssen K. Plattner HP. Sewald N. J. Biotechnol.  2007,  129:  316 
• 7 Song ZQ. Zhang QS. Org. Lett.  2009,  11:  4882 
• 8 Hulme C. Dietrich J. Mol. Diversity  2009,  13:  195 
• 9 Wessjohann LA. Rivera DG. Vercillo OE. Chem. Rev.  2009,  109:  796 
• 10a Jiao CY. Alves ID. Point V. Lavielle S. Sagan S. Chassaing G. Bioconjugate Chem.  2010,  21:  352 
• 10b Fleming SA. Tetrahedron  1995,  51:  1249 
• 11a Suchanek M. Radzikowska A. Thiele C. Nature Meth.  2005,  2:  261 
• 11b Durek T. Zhang J. He C. Kent SBH. Org. Lett.  2007,  9:  5497 
• 11c Sieber SA. Niessen S. Hoover HS. Cravatt BF. Nature Chem. Biol.  2006,  2:  274 
• 12 Church RFR. Weiss MJ. J. Org. Chem.  1970,  35:  2465 
• 13 Ngouansavanh T. Zhu JP. Angew. Chem. Int. Ed.  2006,  45:  3495 
• 14 Kreye O. Westermann B. Wessjohann LA. Synlett  2007,  3188 
• 15 Kuhn C. S. Lehmann J. Sandhoff K. Bioconjugate Chem.  1992,  3:  230 
• 16 Pittelkow M. Lewinsky R. Christensen JB. Synthesis  2002,  2195