1996
DOI: 10.1002/(sici)1099-1344(199612)38:12<1113::aid-jlcr925>3.0.co;2-6
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Synthesis of a P-1-tethered photoaffinity label for inositol hexakisphosphate binding proteins

Abstract: SUMMARYA new photoaffinity analog of inositol hexakisphosphate (InsPs, or phytic acid) was prepared for investigation of InsP6-binding proteins. The racemic P-l-(O-8aminohexyl) derivative of lnsP6 was synthesized in six steps from inositol, and a tritium-labeled benzophenone-containing photophore was attached in the final step to give P-1 [3H]BZDC-lnsP6 (sp. act. 35 Cilmmol).

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Cited by 8 publications
(10 citation statements)
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“…The P-1-linked 3-aminopropylphosphodiesters of Dmyo-IP 3 (18) and IP 4 (22), and the P-2-linked 6-aminohexylphosphodiester of meso-IP 6 (24) were prepared as described previously. The racemic P-1-linked 6-aminohexyl derivative of IP 6 was prepared by modification of the protecting group strategy developed for the P-2-linked probe (23). Each probe had the same nominal specific activity, between 35 and 42 Ci/mmol, as determined by the specific activity of the lot of [ 3 H]BZDC-NHS ester employed.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The P-1-linked 3-aminopropylphosphodiesters of Dmyo-IP 3 (18) and IP 4 (22), and the P-2-linked 6-aminohexylphosphodiester of meso-IP 6 (24) were prepared as described previously. The racemic P-1-linked 6-aminohexyl derivative of IP 6 was prepared by modification of the protecting group strategy developed for the P-2-linked probe (23). Each probe had the same nominal specific activity, between 35 and 42 Ci/mmol, as determined by the specific activity of the lot of [ 3 H]BZDC-NHS ester employed.…”
Section: Resultsmentioning
confidence: 99%
“…The IP 3 binding site of the affinity-purified rat brain IP 3 receptor (19) has been identified by sequencing a proteolytic fragment of the [ 3 H]BZDC-IP 3 photoaffinity-labeled protein (33). The availability of two regioisomeric-tethered derivatives of IP 6 (23,24) has facilitated the further study of kinases (34,35) and other proteins that interact with IP 6 . The P-2-tethered [ 3 H]BZDC-IP 6 prepared in this work was employed to establish the location of the IP 6 binding site in the C2B region of the synaptotagmins and to confirm the ligand specificity of this domain by an independent method.…”
Section: Photolabeling Of Different Domains Of Syt II and Syt Iii Witmentioning
confidence: 99%
“…Inositol hexakisphosphate interacts with a number of proteins implicated in endocytosis regulation, synaptic vesicle trafficking and receptor desensitization (93). The synthesis of P-1 tethered IP6 (39) (94) adds to the previously reported P-2 tethered derivative (38) of IP6 (…”
Section: Phosphoinositides and Ipmentioning
confidence: 94%
“…Oxidation and deprotection (usually catalytic hydrogenolysis) give the desired phosphates in high yields. In addition, methods for the synthesis of inositol phosphites containing deoxy units, tritium, fluorine, and phytoactive groups have also been reported in the literature. Inositol phosphites were made to react with sulfur, which allowed the synthesis of the corresponding phosphorothioates, recommended as inhibitors of some enzymatic reactions …”
Section: A Synthesis Of Phospholipidsmentioning
confidence: 99%
“…Yet another route to this type of complex lipid diphosphites consists of the phosphorylation of protected inositol by lipophosphoramidites. ,, …”
Section: A Synthesis Of Phospholipidsmentioning
confidence: 99%