Probe for measuring phytase activity

Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters

Reexamination Certificate

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C564S186000, C562S020000, C549S220000

Reexamination Certificate

active

07741506

ABSTRACT:
A myo-inositol derivative:R1, R2, R3and R4are identical, being selected from PO3H2, PO3Na2, PO3K2, PO3Li2, PO3Ca, PO3Mg, PO3(NH4)2, PO3(RNH3)2, PO3(R2NH2)2, PO3(R4N)2, PO(OR)2, H, COZ and BHPP, where R is benzyl or alkyl of 1 to 6 carbon atoms and Z is an alkyl or arylalky group providing a cleavable protecting group; R5is one of H, benzyl, 4-methoxybenzyl, COZ, PO3H2, PO3Na2, PO3K2, PO3Li2, PO3Ca, PO3Mg, PO3(NH4)2, PO3(RNH3)2, PO3(R2NH2)2, PO3(R4N)2, PO(OR)2, and BHPP, where R is benzyl or alkyl of 1 to 6 carbon atoms and Z is an alkyl or arylalky group providing a cleavable protecting group; X is one of CH2, CH2CH2O, and CH2CH2CH2O; n is an integer from 1 to 8; L1is a single bond or CH2; L2is one of a single bond, CONH, CH2CONH, CH2CH2CONH, CH2CH2NHCO, CH2CH2NHCONH, CH2CH2NHCSNH, CH2CH2NHSO2, CH2CH2CH2NHCO, CH2CH2CH2NHCONH, CH2CH2CH2NHCSNH, CH2CH2CH2NHSO2, NHCO, NHCONH, NHCSNH, OCONH, CH2, CH2CH2, CH2CH2O, CH2CH2S, CH2CH2NH, CH2CH2CH2, CH2CH2CH2O, CH2CH2CH2S, CH2CH2CH2NH, and NH—SO2; and R6is a UV-visible chromophore, a UV-chromophore, a fluorescent moiety, or a radiolabeled moiety.

REFERENCES:
patent: 2004/0106158 (2004-06-01), Naqvi et al.
Riley et al., Journal of Biological Chemistry, vol. 277, No. 43, 2002, 40290-40295.
Berry and Berry. Tethered phytic acid as a probe for measuring phytase activity. Bioorganic & Medicinal Chemistry Letters 15 (2005) 3157-3161.
Marecek and Prestwich. Synthesis of Tethered Phytic Acid. Tetrahedron Letters vol. 32 No. 16pp. 1863-1866, 1991.
Glenn D. Presiwich. Tethered IP3. Syntesis and Biochemical Applications of the 1-0-(3-Aminopropyl)Ester of Inositol, 1,4,5-Trisphosphate, J. Am. Chem. Soc. 1991. 1822-1825.
Jeroni Morey. A ‘naked eye’ chemosensor system for phytate, Tetrahedron Letters 45 2004, 121-1265, Elsevier Ltd.
Shoichiro Ozaki. Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris (dihydrogen phosphate), J. Chem. Soc. Perkin Trans., 1992, 729-737.
J. Garegg. Synthesis of some mono-O-benzyl-and penta-O-methyl-myo-Inositols*. Carbohydrate Research, 1984, 322-326, Elsevier Science Publishers B.V., Amsterdam.
James F. Marecek. Synthesis of Tethered Phytic Acid. Tetrahedron Letters, 1991, 1863-1866, vol. 32, No. 16.
Wikipedia. Inositol triphosphate, [online], [retrieved on Jan. 22, 2007], retrieved from the Internet <url:http://en.wikipedia.org/wik/Inositol—triphosphate).
Andrew M. Riley. Dimers of D-myo-Inositol 1,4,5-Trisphosphate: Design, Synthesis, and Interaction with Ins(1,4,5) P3 Receptors, Bioconjugate Chem., 2004, 278-289, 15, American Chemical Society.

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