Novel Fluorescent Aminoxy Acids
and Aminoxy Hybrid Peptides

Alan R. Katritzky; Abdelmotaal Abdelmajeid; Srinivasa R. Tala; M. S. Amine; Peter J. Steel

doi:10.1055/s-0030-1258345

PAPER

Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides

Alan R. Katritzky*^a, Abdelmotaal Abdelmajeid^a,b, Srinivasa R. Tala^a, M. S. Amine^b, Peter J. Steel^c
^a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)3920554; e-Mail: katritzky@chem.ufl.edu;
^b Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt
^c Chemistry Department, University of Canterbury, Christchurch, New Zealand

Abstract

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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 (λ_Abs) and the fluorescence emission maxima (λ_Em) 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

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References

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

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