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Synthesis 2010(17): 2997-3003
DOI: 10.1055/s-0030-1258182
DOI: 10.1055/s-0030-1258182
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Photoaffinity-Labeled Peptoids and Depsipeptides by Multicomponent Reactions
Further Information
Received
18 February 2010
Publication Date:
16 July 2010 (online)
Publication History
Publication Date:
16 July 2010 (online)
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
-
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