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Synthesis of Affinity Ligands and Radioactive Probes for Isolation and Study of Myo-Inositol 1,4,5-trisphosphate Binding Proteins

Synthesis of Affinity Ligands and Radioactive Probes for Isolation and Study of Myo-Inositol 1,4,5-trisphosphate Binding Proteins

A N Jina, J Ralph, C E Ballou

Biochemistry. 1990 May 29;29(21):5203-9.

PMID: 2165805

Abstract:

To synthesize an affinity matrix for isolation of D-myo-inositol 1,4,5-trisphosphate binding proteins, racemic 3-cyclohexene-1-carboxaldehyde was oxidized and converted to a mixture of trans-3,4-di-hydroxycyclohexane-1-carboxylic acid methyl ester isomers, which was phosphorylated and separated into (+-)-(1R,3R,4R)- and (+-)-(1R,3S,4S)-trans-3,4-bis[(diphenoxyphosphoryl)oxy]cyclohex an e-1- carboxylic acid methyl esters. Each of these racemic compounds was hydrogenolyzed and reacted with ethylenediamine to give a monoamide, N-(2-aminoethyl)-bis(phosphonyloxy)cyclohexane-1-carboxamide, that was coupled to cyanogen bromide activated Sepharose 4B to provide the desired affinity matrices. The intermediate trans-3,4-bis[(diphenoxyphosphoryl)oxy]cyclohexane-1-carboxylic acid methyl ester was also reduced with lithium borotritide to give the (hydroxy[3H]methyl)cyclohexane derivative, which was phosphorylated and hydrogenolyzed to yield trans-3,4-bis(phosphonyloxy)-1-[(phosphonyloxy)[3H]methyl]cy clohexane, a radiolabeled analogue of inositol 1,4,5-trisphosphate. The carboxamide was also coupled to 4-azidosalicylic acid, and the product was iodinated to provide a 125I-radiolabeled photoactivatable cross-linking derivative of cyclohexanediol bisphosphate.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP31906044	4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde		31906-04-4	Price

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