RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2011(1): 83-90
DOI: 10.1055/s-0030-1258345
DOI: 10.1055/s-0030-1258345
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides
Weitere Informationen
Received
2 September 2010
Publikationsdatum:
30. November 2010 (online)
Publikationsverlauf
Publikationsdatum:
30. November 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201101/lookinside/thumbnails/10.1055-s-0030-1258345-1.jpg)
Abstract
α-Aminoxy acid conjugates and hybrid α-aminoxy dipeptide conjugates showing blue to green fluorescence (with quantum yields 0.23-0.71) were synthesized (75-92% yield) from N-acylbenzotriazoles. 7-Methoxycoumarin derivatives were obtained (quantum yields φ 0.35-0.71) that could be suitable for peptide assays. The wavelengths of the absorption maxima (λAbs) and the fluorescence emission maxima (λEm) and the quantum yields (φ) of some coumarin-3-ylcarbonyl aminoxy acid conjugates were comparable to those of the analogous amino acid derivatives.
Key words
fluorescence - acylations - amino acids - aminoxy acids - peptides
- Supporting Information for this article is available online:
- Supporting Information
- 1
Giepmans BN.Adams SR.Ellisman MH.Tsien RY. Science 2006, 312: 217 - 2
Mayer A.Neuenhofer S. Angew. Chem., Int. Ed. Engl. 1994, 33: 1044 - 3
Zimmer M. Chem. Rev. 2002, 102: 759 - 4
Katritzky AR.Narindoshvili T. Org. Biomol. Chem. 2009, 7: 627 - 5
Reetz MT. Angew. Chem. Int. Ed. 2001, 40: 284 - 6
Battersby BJ.Lawrie GA.Trau M. Drug Discovery Today 2001, 6: S19-S26 - 7
Farrer RA.Copeland GT.Previte MJR.Okamoto MM.Miller SJ.Fourkas JT. J. Am. Chem. Soc. 2002, 124: 1994 - 8
Dragulescu-Andrasi A.Rao J. ChemBioChem 2007, 8: 1099 - 9
Hohsaka T.Ashizuka Y.Taira H.Murakami H.Sisido M. Biochemistry 2001, 40: 11060 - 10
Hohsaka T.Sato K.Sisido M.Takai K. FEBS Lett. 1994, 344: 171 - 11
Yang D.Zhang Y.-H.Li B.Zhang D.-W.Chan JC.-Y.Zhu N.-Y.Luo S.-W.Wu Y.-D. J. Am. Chem. Soc. 2004, 126: 6956 - 12
Briggs MT.Morley JS. J. Chem. Soc., Perkin Trans. 1 1979, 2138 - 13
Hill DJ.Mio MJ.Prince RB.Hughes TS.Moore JS. Chem. Rev. 2001, 101: 3893 - 14
Yang D.Zhang D.-W.Hao Y.Wu Y.-D.Luo S.-W.Zhu N.-Y. Angew. Chem. Int. Ed. 2004, 43: 6719 - 15
Li X.Yang D. Chem. Commun. 2006, 3367 - 16
Jimenez-Castells C.de la Torre BG.Gallego RG.Andreu D. Bioorg. Med. Chem. Lett. 2007, 17: 5155 - 17
Carrasco MR.Nguyen MJ.Burnell DR.MacLaren MD.Hengel SM. Tetrahedron Lett. 2002, 43: 5727 - 18
Carrasco MR.Brown RT. J. Org. Chem. 2003, 68: 8853 - 19
Vanderesse R.Thevenet L.Marraud M.Boggetto N.Reboud M.Corbier C. J. Pept. Sci. 2003, 9: 282 - 20
Wu Y.-D.Wang D.-P.Chan KWK.Yang D. J. Am. Chem. Soc. 1999, 121: 11189 - 21
Chandrasekhar S.Rao CL.Reddy MS.Sharma GD.Kiran MU.Naresh P.Chaitanya GK.Bhanuprakash K.Jagadeesh B. J. Org. Chem. 2008, 73: 9443 - 22
Chen F.Song K.-S.Wu Y.-D.Yang D. J. Am. Chem. Soc. 2008, 130: 743 - 23
Esteves AP.Rodrigues LM.Silva ME.Gupta S.Oliveira-Campos AMF.Machalicky O.Mendonça AJ. Tetrahedron 2005, 61: 8625 - 24
Sui G.Kele P.Orbulescu J.Huo Q.Leblanc RM. Lett. Pept. Sci. 2002, 8: 47 - 25
Heiner S.Detert H.Kuhn A.Kunz H. Bioorg. Med. Chem. 2006, 14: 6149 - 26
Katritzky AR.Narindoshvili T.Angrish P. Synthesis 2008, 2013 - 27
Sivakumar K.Xie F.Cash BM.Long S.Barnhill HN.Wang Q. Org. Lett. 2004, 6: 4603 - 28
Zhou Z.Fahrni CJ. J. Am. Chem. Soc. 2004, 126: 8862