Synthesis and biological action of novel 4-position-modified derivatives of D-myo-Inositol 1,4,5-trisphosphate

被引：17
作者：
Bello, Davide
Aslam, Tashfeen
Bultynck, Geert
Slawin, Alexandra M. Z.
Roderick, H. Llewelyn
Bootman, Martin D.
Conway, Stuart J. [1 ]
机构：
[1] Univ St Andrews, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[2] Univ St Andrews, Sch Chem, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland
[3] Katholieke Univ Leuven, Mol Signalling Lab, B-3000 Louvain, Belgium
[4] Babraham Inst, Mol Signalling Lab, Cambridge CB22 3AT, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期
基金：
英国生物技术与生命科学研究理事会;
关键词：
D O I：
10.1021/jo070611a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The design of a range of 4-position-modified D-myo-inositol 1,4,5-trisphosphate derivatives is described. The enantioselective synthesis of these compounds is reported, along with initial biological analysis, which indicates that these compounds do not act as D-myo-inositol 1,4,5-trisphosphate receptor agonists or antagonists.
引用
收藏
页码：5647 / 5659
页数：13
相关论文
共 43 条
[21]   Synthesis and biological evaluation of a PtdIns(4,5)P2 and a phosphatidic acid affinity matrix [J].
Lim, ZY ;
Thuring, JW ;
Holmes, AB ;
Manifava, M ;
Ktistakis, NT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, Royal Society of Chemistry (08) :1067-1075
[22]   Stable overexpression of the type-1 inositol 1,4,5-trisphosphate receptor in L fibroblasts: Subcellular distribution and functional consequences [J].
Mackrill, JJ ;
Wilcox, RA ;
Miyawaki, A ;
Mikoshiba, K ;
Nahorski, SR ;
Challiss, RAJ .
BIOCHEMICAL JOURNAL, 1996, 318 :871-878
[23]  
Maruyama T, 1997, J BIOCHEM-TOKYO, V122, P498
[24]   Convergent synthesis of adenophostin A analogues via a base replacement strategy [J].
Marwood, RD ;
Shuto, S ;
Jenkins, DJ ;
Potter, BVL .
CHEMICAL COMMUNICATIONS, 2000, (03) :219-220
[25]   Synthesis of adenophostin A [J].
Marwood, RD ;
Correa, V ;
Taylor, CW ;
Potter, BVL .
TETRAHEDRON-ASYMMETRY, 2000, 11 (02) :397-403
[26]   THE LIGAND-BINDING SITE AND TRANSDUCTION MECHANISM IN THE INOSITOL-1,4,5-TRIPHOSPHATE RECEPTOR [J].
MIGNERY, GA ;
SUDHOF, TC .
EMBO JOURNAL, 1990, 9 (12) :3893-3898
[27]   EXPRESSED CEREBELLAR-TYPE INOSITOL 1,4,5-TRISPHOSPHATE RECEPTOR, P400, HAS CALCIUM RELEASE ACTIVITY IN A FIBROBLAST L-CELL LINE [J].
MIYAWAKI, A ;
FURUICHI, T ;
MAEDA, N ;
MIKOSHIBA, K .
NEURON, 1990, 5 (01) :11-18
[28]   Determinants of adenophostin A binding to inositol trisphosphate receptors [J].
Morris, SA ;
Nerou, EP ;
Riley, AM ;
Potter, BVL ;
Taylor, CW .
BIOCHEMICAL JOURNAL, 2002, 367 :113-120
[29]   STRUCTURES OF XESTOSPONGIN-A, XESTOSPONGIN-B, XESTOSPONGIN-C AND XESTOSPONGIN-D, NOVEL VASODILATIVE COMPOUNDS FROM MARINE SPONGE, XESTOSPONGIA-EXIGUA [J].
NAKAGAWA, M ;
ENDO, M ;
TANAKA, N ;
LEE, GP .
TETRAHEDRON LETTERS, 1984, 25 (30) :3227-3230
[30]   Synthesis and biological evaluation of a PtdIns(3,4,5)P3 affinity matrix [J].
Painter, GF ;
Thuring, JW ;
Lim, ZY ;
Holmes, AB ;
Hawkins, PT ;
Stephens, LR .
CHEMICAL COMMUNICATIONS, 2001, (07) :645-646
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