A photoactivable amino acid based on a novel functional coumarin-6-yl-Alanine

Amino Acids

Volumn 43, Issue 6, 2012, Pages 2329-2338

  Fonseca, Andrea Sc ^a   Goncalves, M Sameiro T ^a   Costa, Susana P G ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Amino acid conjugates; Coumarin; Coumarin 6 yl Alanine; Fluorescence; Photolysis

Indexed keywords

ALANINYL COUMARIN 6 YL ALANINE ESTER CONJUGATE; AMINO ACID; COUMARIN 6 YL ALANINE METHYL ESTER CONJUGATE; LEVO CHLOROMETHYLCOUMARIN 6 YL ALANINE; N ACETYL (4 CHLOROMETHYL) COUMARIN 6 YL ALANYLALANINE METHYL ESTER; N ACETYL LEVO (3 CHLOROMETHYL)BEZOFURAN 5 YL ALANINE METHYL ESTER; N ACETYL LEVO (4 CHLOROMETHYL)COUMARIN 6 YL ALANINE METHYL ESTER; N ACETYL LEVO ALANINYL (4 CHLOROMETHYL) COUMARIN 6 YL ALANINE METHYL ESTER; N ACETYLALANYLTYROSINE METHYL ESTER; N ACETYLTYROSINYLALANINE METHYL ESTER; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; PHOTOCHEMICAL REACTOR; PHOTOLYSIS; PHOTOREACTIVITY; PRIORITY JOURNAL; REACTOR; ULTRAVIOLET RADIATION;

ALANINE; COUMARINS; FLUORESCENCE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; SPECTROMETRY, FLUORESCENCE; TYROSINE;

EID: 84872686114     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-012-1310-2     Document Type: Article

References (25)

1. Bennett FA, Barlow DJ, Dodoo ANO, Hider RC, Lansley AB, Lawrence MJ, Marriott C, Bansal SS (1997) L-(6,7-Dimethoxy-4-coumaryl) alanine: An intrinsic probe for the labelling of peptides. Tetrahedron Lett 38:7449-7452 (Pubitemid 27435152)
2. Brun MP, Bischoff L, Garbay C (2004) A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids. Angew Chem Int Ed 43:3432-3436 (Pubitemid 39257556)
3. Corrie JET, Furuta T, Givens R, Yousef AL, Goeldner M (2005) In: Goeldner M, Givens RS (eds.) Dynamic studies in biology: phototriggers photoswitches and caged biomolecules. Wiley, Weinheim, pp 1-94
4. Fernandes MJG, Goncalves MST, Costa SPG (2008) Comparative study of polyaromatic and polyheteroaromatic fluorescent photocleavable protecting groups. Tetrahedron 64:3032-3038
5. Fonseca ASC, Goncalves MST, Costa SPG (2007) Photocleavage studies of fluorescent amino acid conjugates bearing different types of linkages. Tetrahedron 63:1353-1359 (Pubitemid 44969415)
6. Fonseca ASC, Goncalves MST, Costa SPG (2010) Light-induced cleavage of model phenylalanine conjugates based on coumarins and quinolones. Amino Acids 39:699-712
7. Geissler D, Antonenko YN, Schmidt R, Keller S, Krylova OO, Wiesner B, Bendig J, Pohl P, Hagen V (2005) (Coumarin-4-yl)methyl esters as highly efficient, ultrafast phototriggers for protons and their application to acidifying membrane surfaces. Angew Chem Int Ed 44:1195-1198 (Pubitemid 40394734)
8. Gilbert D, Funk K, Dekowski B, Lechler R, Keller S, Mohrlen F, Frings S, Hagen V (2007) Caged capsaicins: new tools for the examination of TRPV1 channels in somatosensory neurons. ChemBioChem 8:89-97 (Pubitemid 46121575)
9. Grunwald C, Schulze K, Reichel A, Weiss VU, Blaas D, Piehler J, Wiesmu ller KH, Tampea R (2010) In situ assembly of macromolecular complexes triggered by light. Proc Nat Acad Sci USA 107:6146-6151
10. Guillier F, Orain D, Bradley M (2000) Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem Rev 100:2091-2158
11. Hagen V, Dekowski B, Nache V, Schmidt R, Geissler D, Lorenz D, Eichhorst J, Keller S, Kaneko H, Benndorf K, Wiesner B (2005) Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one-And two-photon photolysis. Angew Chem Int Ed 44:7887-7891 (Pubitemid 41811701)
12. Katritzky AR, Narindoshvili T (2009) Fluorescent amino acids: Advances in protein-extrinsic fluorophores. Org Biomol Chem 7:627-634
13. Kele P, Sui G, Huo Q, Leblanc RM (2000) Highly enantioselective synthesis of a fluorescent amino acid. Tetrahedron Assymetry 11:4959-4963 (Pubitemid 32155307)
14. Kumita JR, Smart OS, Woolley GA (2000) Photo-control of helix content in a short peptide. Proc Nat Acad Sci USA 97:3803-3808 (Pubitemid 30226042)
15. Li YM, Shi J, Luo ZF, Jiang H, Chen XY, Wang FL, Wu X, Guo KX (2009) Photoregulation of thrombin aptamer activity using Bhc caging strategy Bioorg. Med Chem Lett 19:5368-5371
16. Lin W, Lawrence DS (2002) A strategy for the construction of caged diols using a photolabile protecting group. J Org Chem 67:2723-2726 (Pubitemid 34298898)
17. Mayer G, Heckel A (2006) Biologically active molecules with a light switch. Angew Chem Int Ed 45:4900-4921 (Pubitemid 44166118)
18. Morris JV, Mahaney MA, Huber JR (1976) Fluorescence quantum yield determinations. 9,10-Diphenylanthracene as a reference standard in different solvents. J Phys Chem 80:969-974
19. Muller C, Even P, Viriot ML, Carre MC (2001) Protection and labelling of thymidine by a fluorescent photolabile group. Helv Chim Acta 84:3735-3741
20. Piloto AM, Fonseca ASC, Costa SPG, Goncalves MST (2006) Carboxylic fused furans for amino acid fluorescent labeling. Tetrahedron 62:9258-9267 (Pubitemid 44205187)
21. Schmidt R, Geissler D, Hagen V, Bendig J (2007) Mechanism of photocleavage of (coumarin-4-yl)methyl esters. J Phys Chem A 111:5768-5774 (Pubitemid 47166780)
22. Shembekar VR, Chen Y, Carpenter BK, Hess GP (2007) Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids. Biochemistry 46:5479-5484
23. Soares AMS, Costa SPG, Goncalves MST (2010a) 2-Oxo-2Hbenzo[ h]benzopyran as a new light sensitive protecting group for neurotransmitter amino acids. Amino Acids 39:121-133
24. Soares AMS, Costa SPG, Goncalves MST (2010b) Oxazole light triggered protecting groups: synthesis and photolysis of fused heteroaromatic conjugates. Tetrahedron 66:8189-8195
25. Yamaji M, Nozali K, Allonas X, Nakajima S, Tero-Kubota S, Marciniak B (2009) Photoinduced bond dissociation of 4-methylcoumarin derivatives in solution studied by laser flash photolysis and DFT calculations. J Phys Chem A 113:5815-5822