Enantiomerically convergent synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate from both L- and D-1,2-0-cyclohexylidene-myo-inositol

被引：7

作者：

Han, FS

Hayashi, M

Watanabe, Y ^{[1
]}

机构：

[1] Ehime Univ, Venture Business Lab, Matsuyama, Ehime 7908577, Japan

[2] Ehime Univ, Fac Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 08期

关键词：

D O I：

10.1246/cl.2003.724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate [PtdIns(3,5)P2] has been conveniently accomplished via convergent routes starting from both enantiomers, 1,2-O-cyclohexylidene-myo-inositol. The synthetic strategy involves completely regioselective phosphorylation of 3,4-diol and 2,3,6-triol of the suitably protected inositols with the corresponding phosphite in the presence of pyridinium tribromide and 2,6-lutidine, resulting in the formation of 3-O-phosphorylated products, respectively.

引用

页码：724 / 725

页数：2

共 50 条

[41] ENZYMIC-SYNTHESIS OF "1-0-INDOL-3-YLACETYL-BETA-D-GLUCOSE AND INDOL-3-YLACETYL-MYO-INOSITOL
MICHALCZUK, L
BANDURSKI, RS
BIOCHEMICAL JOURNAL, 1982, 207 (02) : 273 - 281
[42] The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphate
Desai, T
Gigg, J
Gigg, R
MartinZamora, E
CARBOHYDRATE RESEARCH, 1996, 296 : 97 - 133
[43] SYNTHESIS OF OPTICALLY-ACTIVE 2,3,6-TRI-O-BENZYL-D-MYO-INOSITOL FROM D-GLUCOSE
SATO, K
SAKUMA, S
MURAMATSU, S
BOKURA, M
CHEMISTRY LETTERS, 1991, (08) : 1473 - 1474
[44] SYNTHESIS AND CA2+-RELEASE ACTIVITY OF D-MYO-INOSITOL 2,4,5-TRISPHOSPHATE AND L-MYO-INOSITOL 2,4,5-TRISPHOSPHATE, AND 2,4,5-TRISPHOSPHATE AND D-CHIRO-INOSITOL 1,3,4-TRISPHOSPHATE AND L-CHIRO-INOSITOL 1,3,4-TRISPHOSPHATE
TEGGE, W
DENIS, GV
BALLOU, CE
CARBOHYDRATE RESEARCH, 1991, 217 : 107 - 116
[45] Sulfonate protecting groups.: Regioselective sulfonylation of myo-inositol orthoesters -: improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives (vol 337, pg 2399, 2002)
Sureshan, KM
Shashidhar, MS
Praveen, T
Gonnade, RG
Bhadbhade, MM
CARBOHYDRATE RESEARCH, 2003, 338 (10) : 1147 - 1147
[46] TOTAL SYNTHESIS OF THE 2ND MESSENGER ANALOG D-MYO-INOSITOL 1-PHOSPHOROTHIOATE 4,5-BISPHOSPHATE - OPTICAL RESOLUTION OF DL-1-O-ALLYL-2,3,6-TRI-O-BENZYL-MYO-INOSITOL AND FLUORESCENT LABELING OF MYOINOSITOL 1,4,5-TRISPHOSPHATE
LAMPE, D
MILLS, SJ
POTTER, BVL
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21): : 2899 - 2906
[47] SYNTHESIS FROM QUEBRACHITOL OF 1L-CHIRO-INOSITOL 2,3,5-TRISPHOSPHATE, AN INHIBITOR OF THE ENZYMES OF 1D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE METABOLISM
LIU, CS
NAHORSKI, SR
POTTER, BVL
CARBOHYDRATE RESEARCH, 1992, 234 : 107 - 115
[48] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY .29. THE PREPARATION OF INTERMEDIATES FOR THE SYNTHESIS OF 1D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND 2,4,5-TRISPHOSPHATE, 1,4-BISPHOSPHATE 5-PHOSPHOROTHIOATE, AND 4,5-BISPHOSPHATE 1-PHOSPHOROTHIOATE FROM 1D-3,6-DI-O-BENZYL-1,2-O-ISOPROPYLIDENE-MYO-INOSITOL
DESAI, T
GIGG, J
GIGG, R
MARTINZAMORA, E
CARBOHYDRATE RESEARCH, 1994, 262 (01) : 59 - 77
[49] Diastereoselective synthesis of D- and L-myo-inositol 3,4,5,6-tetrakisphosphates from D-glucose via dihydroxylation of (+)-conduritol B derivatives
Saito, S
Shimazawa, R
Shirai, R
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (06) : 727 - 732
[50] Convenient synthesis of 3- and 6-deoxy-D-myo-inositol phosphate analogues from (+)-epi- and (-)-vibo-quercitols
Ogawa, Seiichiro
Tezuka, Yoji
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) : 5238 - 5243

← 1 2 3 4 5 →