Labeling methods with oxygen isotopes

Details Labeling methods with oxygen isotopes Labeling methods with oxygen isotopes

2011-03-08

2011-03-08

Desai, Anand U (Department: 1656)

Chemistry: natural resins or derivatives; peptides or proteins;

Proteins, i.e., more than 100 amino acid residues

C424S009300, C536S023100

Reexamination Certificate

active

07902333

ABSTRACT:
The present invention provides methods for labeling One or two oxygen atom(s) in a carboxyl group of a carboxyl-containing compound with an oxygen isotope selected from oxygen-17 (17O) or oxygen-18 (18O). The methods of the present invention are characterized in that an activated ester of the carboxyl-containing compound (carboxylic acid) is reacted with H217O or H218O in the presence of an activator. In the methods of the present invention, the reaction between the activated ester of a carboxylic acid and H217O or H218O can be allowed to proceed without including drastic conditions such as strongly acidic conditions or alkaline hydrolysis because an activator is used.

REFERENCES:
Fuller, JC Jr. et al., “Use of 18O-labelled leucine and phenylalanine to measure protein turnover in muscle cell cultures and possible futile cycling during aminoacylation”, Biochem J. 294(Pt 2): 427-433 (1993).
Ponnusamy, E. et al., “Synthesis of 17O isotope labeled Leu-enkephalin and 17O n.m.r.”, (Int. J. Pept. Protein Res. 32(1): 21-27 (Jul. 1988); Abstract only).
Jones, John, Amino Acid and Peptide Synthesis, Oxford 2nd Ed., 2002, p. 35.
Gerothanassis, et al.,17ONMR Chemical Shifts of the Twenty Protein Amino Acids in Aqueous Solution, Magnetic Resonance in Chemistry, vol. 23, No. 8, 1985, pp. 659-665.
Ponnusamy et al., Synthesis of Oxygen-17 Labeled Thyrotropin Releasing Hormone, Journal of Labelled Compounds and Radiopharmaceuticals, 1985, vol. 22, No. 11, pp. 1135-1141.
Kabalka, G.W., et al., “17O Enrichment Methods,”17O NMR Spectroscopy in Organic Chemistry, pp. 28-29, (1991).
Steinschneider et al., International Journal of Applied Radiation and Isotopes, 1981, vol. 32, No. 2, pp. 120-121.
Steinschneider et al., International Journal of Peptide & Protein Research, 1981, vol. 18, No. 3, pp. 324-333.
Ponnusamy et al., Journal of Labelled Compounds and Radiopharmaceuticals, 1987, vol. 24, No. 7, pp. 773-778.

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