Synthesis, acid-base behavior, and binding properties of 6-modified myo-inositol 1,4,5-tris (phosphate)s

Authors
Ballereau, S Guedat, P Poirier, SN Guillemette, G Spiess, B Schlewer, G
Citation
S. Ballereau et al., Synthesis, acid-base behavior, and binding properties of 6-modified myo-inositol 1,4,5-tris (phosphate)s, J MED CHEM, 42(23), 1999, pp. 4824-4835
Citations number
45
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF MEDICINAL CHEMISTRY
ISSN journal
00222623 → ACNP
Volume
42
Issue
23
Year of publication
1999
Pages
4824 - 4835
Database
ISI
SICI code
0022-2623(19991118)42:23<4824:SABABP>2.0.ZU;2-Y
Abstract
myo-Inositol 1,4,5-tris(phosphate) was modified at position 6. The analogue s synthesized are reported in this publication are 6-deoxy-myo-inositol 1,4 ,5-tris(phosphate), 6-fluoro-6-deoxy-myo-inositol 1,4,5-tris(phosphate), ep i-inositol 1,4,5-tris(phosphate), and 6-amino-6-deoxy-myo-inositol 1,4,5-tr is(phosphate). These derivatives showed poor affinity for the Ins(1,4,5)P-3 receptors. The inframolecular acid-base behavior and the cooperative effec ts between the phosphate groups could help explain the loss of affinity of these 6-modified analogues.