Phenyldiazirine compounds and photoaffinity labeling reagent

Details Phenyldiazirine compounds and photoaffinity labeling reagent Phenyldiazirine compounds and photoaffinity labeling reagent

2005-06-07

2005-06-07

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S954000, C548S959000

Reexamination Certificate

active

06903223

ABSTRACT:
This invention offers a photoreactive labeling reagent consisting of a novel biotinylated phenyldiazirine compound; a photoaffinity labeling reagent consisting of a saccharide-linked biotinylated phenyldiazirine compound where a saccharide compound is introduced into the novel compound; and a novel diazirine compound for such a reagent. The invention covers a biotinylated phenyldiazirine compound of the following formula (II); a phenyldiazirine compound which is an intermediate for synthesizing the above; a saccharide-linked biotinylated phenyldiazirine compound derived from the compound of the formula (II) and a saccharide compound and a method for manufacturing the same; a photoreactive labeling reagent containing the compound of the formula (II); a photoaffinity labeling reagent containing the saccharide-linked biotinylated phenyldiazirine compound; and a method for labeling a saccharide receptor using the reagent.

REFERENCES:
Yasumaru Hatanaka, et al., “Diazirine-Based Photoaffinity Labeling: Chemical Approach to Biological Interfaces”, Reviews on Heteroatom Chemistry, vol. 14, pp. 213-243 (1996).
Yasumaru Hatanaka, “Organic Chemistry for Structural Biology: Probing the Functional Structure of Proteins by Photoaffinity Labeling”, vol. 56, No. 7, pp. 581-590 (1998).
Makoto Hashimoto, et al., “Identification of Photolabeled Peptides for the acceptor Substrate Binding Domain of β1, 4-Galactosyltransferase”, Chem. Pharm. Bull., vol. 47(5), pp. 667-671 (May 1999).
Yasumaru Hatanaka, et al. “A Novel Biotinylated Heterobifunctional Cross-Linking Reagent Bearing an Aromatic Diazirine”, Bioorganic & Medicinal Chemistry, vol. 2, No. 12, pp. 1367-1373 (1994).
Françoise Koumanov, et al., “Cell-Surface Biotinylation of Glut4 Using Bis-Mannose Photolables”, Biochem J., vol. 330, pp. 1209-1215 (1998).
Yasumaru Hatanaka, et al., “A Rapid and Efficient Method for Identifying Photoaffinity Biotinylated Sites Within Proteins”, J. Am. Chem. Soc., vol. 120, pp. 453-454 (1998).
Yasumaru Hatanaka, et al., “Synthesis and Characterization of a Carbene-Generating Biotinylated N-Acetylglucosamine for Photoaffinity Labeling of β-(1→4)-Galactosyltransferase”, Carbohydrate Research, vol. 294, pp. 95-108 (1996).
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