Synthesis of PI(3,4,5)P3 with unsaturated and saturated fatty acid chains

被引:17
作者
Watanabe, Y [1 ]
Nakatomi, M [1 ]
机构
[1] Ehime Univ, Fac Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan
关键词
phosphatidyl inositol; phospholipid; natural product; protecting group;
D O I
10.1016/S0040-4020(99)00551-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of three PI(3,4,5)P(3)s, sn-1-O-stearoyl-sn-2-O-arachidonoyl, stearoyl-linolenoyl, and distearoyl phosphatidyl-myo-inositol 3,4,5-trisphosphate with the natural configuration for the arachidonoyl version was established by employing 9-fluorenylmethyl-protected phosphate derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9743 / 9754
页数:12
相关论文
共 29 条
[1]   A unified approach to unambiguous synthesis of the phosphatidylinositol-3-phosphates involved in intracellular signal transduction [J].
Aneja, SG ;
Parra, A ;
Stoenescu, C ;
Xia, WY ;
Aneja, R .
TETRAHEDRON LETTERS, 1997, 38 (05) :803-806
[2]   PDGF-DEPENDENT TYROSINE PHOSPHORYLATION STIMULATES PRODUCTION OF NOVEL POLYPHOSPHOINOSITIDES IN INTACT-CELLS [J].
AUGER, KR ;
SERUNIAN, LA ;
SOLTOFF, SP ;
LIBBY, P ;
CANTLEY, LC .
CELL, 1989, 57 (01) :167-175
[3]   INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].
BERRIDGE, MJ .
NATURE, 1993, 361 (6410) :315-325
[4]   GENERAL-SYNTHESIS OF PHOSPHATIDYLINOSITOL 3-PHOSPHATES [J].
BRUZIK, KS ;
KUBIAK, RJ .
TETRAHEDRON LETTERS, 1995, 36 (14) :2415-2418
[5]   SYNTHESIS OF METHYL (METHYL D-IDOPYRANOSID AND L-IDOPYRANOSID)URONATES - FROM MYOINOSITOL [J].
CHIDA, N ;
YAMADA, E ;
OGAWA, S .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (03) :555-570
[6]  
DESAI T, 1996, SPEC PUBL ROYAL SOC, V180, P67
[7]  
DUCKWORTH BC, 1996, HANDB LIP R, V8, P125
[8]   Synthesis of 1-O-stearoyl-2-O-arachidonoyl-sn-glycer-3-yl-D-myo-inositol 3,4,5-trisphosphate and its stereoisomers [J].
Gaffney, PRJ ;
Reese, CB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (24) :3171-3176
[9]  
GOU DM, 1994, J CHEM SOC CHEM COMM, P215
[10]  
GROVE SJA, 1997, J CHEM SOC CHEM COMM, P1635