Synthetic peptides for the detection of trimethylamine (TMA)...

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 11 to 14 amino acid residues in defined sequence

Reexamination Certificate

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C530S328000, C530S329000, C514S014800, C514S015800, C514S016700, C514S017400

Reexamination Certificate

active

06218507

ABSTRACT:

FIELD OF THE INVENTION
The present invention is directed to a peptide and the analogues thereof capable of detecting trirnethylamine, and a method and a device for detecting trimethylamine using the peptides.
BACKGROUND OF THE INVENTION
Trinethylamine (TMA) is an offensively smelling gas having an irritating, fishy and ammonia-like odor, and is a listed substance under restriction control according to the regulations on the air pollution control act. With respect to the quality control in food industry, the amount of volatile alkali substance such as trimethylanine will increase during the putrefaction of seafood (e.g. fish and shrimp). Therefore, the level of putrefaction of seafood can be indicated by the detection of the amount of trimethylamine present (Nonaka, J. et al., Bull. Japan Soc. Sci. Fish, Vol. 58, pp. 2039-2044, 1967). With respect to medical diagnosis, an increase of concentration of trimethylamine in the breath of patients can be used as an index of virernic diseases. (Siminhoff, M. L. et al., N. Engl. J. Med. Vol. 297, pp. 132-135, 1977). Therefore, the techniques for detecting trimethylamine are applicable in the fields of environmental protection, food industry and medical diagnosis.
In general, trimethylamine is determined by, for instance, acid titration and instrumental analysis such as gas chromatography, and mass spectrometry. However, such methods have some disadvantages, such as which involve complicated operation procedures, and are time-costing and difficult to analysis.
In view of the fact that various odorant molecules are identified by olfactory organs due to the binding of the odorant molecules and the receptor proteins on olfactory cilia (ancet D., Annu. Rev. Neurosci, Vol. 9, pp. 227-255, 1986). In 1991, the gene family of the olfactory receptor proteins were cloned and characterized. The protein sequences of the odorant receptors were determined by Buck and Axel (Buck, L. and Axel, R, Cell Vol. 65, pp. 175-187, 1991). In addition, a device for identifying the aroma of the wine through the binding by an olfactory receptor protein of a bullfrog was published (Wu, T. Z., and Wan, H. H., Analytical Science Vol. 7, Supplement, pp.867-870, 1991).
SUMMARY OF THE INVENTION
The present invention provides a peptide and the analogues thereof capable of detecting trimethylamine, which is a fragment of an olfactory receptor protein. The disadvantages occurring in the prior art have been eliminated by the invention.
An object of the present invention is to provide a peptide capable of detecting trimethylamine, which comprises the following amino acid sequence:
Cys-Pro-Ser-Ala-Asn-Asn-Ser-Thr-Val-Lys-Glu   (SEQ ID) NO.1).
Another object of the present invention is to provide an analogue of the peptide, which comprises one of the following sequences:
Cys-Pro-Ser-Ala-Asn-Asn-Ser-Thr
(SEQ ID NO.2);

Cys-Pro-Ser-AIa-Asn-Asn
(SEQ ID NO.3);

and

Cys-Asn-Ser-Thr-Val-Lys-Glu
(SEQ ID NO.4).
A further object of the invention is to provide a peptide capable of detecting trimethylamine and binding to a piezoelectric crystal, which comprises the peptide as defined above and a spacer binding the carboxy-terniinal of the peptide to a piezoelectric crystal. The preferred embodiments include as follows:
Cys-Pro-Ser-Ala-Asn-Asn-Ser-Thr-Val-Lys-Glu-Gly-Cys-Gly
(Peptide I, SEQ ID No. 5);

Cys-Pro-Ser-Ala-Asn-Asn-Ser-Thr-Gly-Cys-Gly
(Peptide II, SEQ ID No. 6);

Cys-Pro-Ser-Ala-Asn-Asn-Gly-Cys-Gly
(Peptide III, SEQ ID No. 7); and

Cys-Asn-Ser-Thr-Val-Lys-Glu-Gly-Cys-Gly
(Peptide IV, SEQ ID No. 8).
In preferred embodiments, the spacer is -Gly-Cys-Gly, Ala-Cys-Ala, Ala-Cys, Gly-Cys- or Cys.
A further another object of the invention is to provide a method for detecting trimethylamine.
Also, the present invention provides a device for detecting trimethylamine.


REFERENCES:
patent: WO92/17585 (1992-10-01), None
patent: WO94/05695 (1994-03-01), None
Ngo et al., ‘Computational Complexity, Potein Structure Prediction, and the Levinthal Paradox,’ The Protein Folding Problem and Tertiary Structuer Prediction. Ed. K. Merz and L. Le Grand. BirkHauser, Boston MA. pp. 491-495, 1994.*
Rudinger, J. (1976). Peptide Hormones (ed. J.A. Parsons). University Park Press. Baltimore. pp. 1-7, 1976.*
Buck et al., “A Novel Multigene Family May Encode Odorant Receptors: A Molecular Basis for Odor Recognition”, Dept. of Biochemistry and Molecular Biophysics, vol. 65, (175-187, Apr. 5, 1991).
Xiao S., “Abstract”,Database WPI, Section Ch, Week 199531, Derwent Publications Ltd., London, 1995.
Tokyo Shibaura Electric Co., “Abstract”,Database WPI, Section Ch, Week 197384, Derwent Publications Ltd., London, 1978.
Application of PZ-Olfactory Biosensor for the Quality Assesments of Sorghum Liquor,Analytical Sciences, vol. 7, Supplement, pp. 867-870, 1991.
A Novel Multigene Family May Encode Odorant Receptors: A Molecular Basis for Odor Recognition,Cell, vol. 65, pp. 175-187, 1991.
Nonaka, J. et al., “Bulletin of the Japanese Society of Scientific Fisheries”, vol. 58, pp. 2039-2044 (1967).
Siminhoff, M.L. et al., “The New England Journal of Medicine”, vol. 297, pp. 132-135 (1977).
Lancet, D., “Annual Review of Neuroscience”, vol. 9, pp. 227-255 (1986).
Buck. L. and Axel, R., “A Novel Multigene Family May Encode Odorant Receptors: A Molecular Basis for Odor Recognition”, vol. 65, pp. 175-187 (1991).
Wu, T.Z. and Wan, H.H., “Analytical Science” vol. 7, Supplement, pp. 867-870 (1991).

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