Fluorescent amino acid derivative and production method of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C530S300000

Reexamination Certificate

active

07847098

ABSTRACT:
The present invention provides a fluorescent amino acid derivative which can be synthesized by simple steps, can be excited particularly by a blue laser ray region of visible light, and has an improved light stability. These objects can be achieved by a fluorescent amino acid derivative which is an acridone derivative substituted with an amino acid to comprise an electrophilic substituent group between the amino acid and the acridone derivative. Instead of a conventional strategy that aminophenylalanine is used as a starting material to form a fluorescent group through a coupling reaction and an intramolecular cyclization reaction, a fluorescent acridone derivative is used as a starting material to furnish the material to a reactive group by a position-specific electrophilic substitution reaction, and then the acridone derivative having the reactive group is allowed to couple with an amino acid derivative.

REFERENCES:
patent: 05-043574 (1993-02-01), None
patent: 2005-287327 (2005-10-01), None
patent: WO 02/099424 (2002-12-01), None
patent: WO 2004/011946 (2004-02-01), None
(http://www.biotech.okayama-u.ac°jp/labs/sisido/sisidol.html.
http://www.biotech.okayama-u.ac.jp/labs/sisido/sisido2.html).
Hamada H, et al, “Position-specific incorporation of a highly photodurable and blue-laser excitable fluorescent amino acid into proteins for fluorescence sensing,” Bioorg Med Chem. May 16, 2005;13(10):3379-84.
Szymaflska et al., “Synthesis of N-[(tert-Butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2- yl)-L-alanine, a New Fluorescent Aminio Acid Derivative,” Helvetica Chimica Acta, vol. 86, 2003, pp. 3326-3331 Applicants IDS.
Szymańska et al., “Synthesis of N-[(tert-Butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2-yl)-L-alanine, a New Fluorescent Amino Acid Derivative,” Helvetica Chimica Acta, vol. 86, 2003, pp. 3326-3331.

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