Regiospecific phosphohydrolases from Dictyostelium as tools for the chemoenzymatic synthesis of the enantiomers D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate:: Non-physiological, potential analogues of biologically active D-myo-inositol 1,3,4-trisphosphate

被引：17

作者：

Adelt, S

Plettenburg, O

Dallmann, G

Ritter, FP

Shears, SB

Altenbach, HJ

Vogel, G

机构：

[1] Berg Univ Gesamthsch Wuppertal, Inst Organ Chem & Biochem, D-42097 Wuppertal, Germany

[2] NIEHS, Lab Signal Transduct, NIH, Res Triangle Pk, NC 27709 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(01)00536-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new de novo synthesis of the enantiomeric pair D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate is described. Starting from enantiopure dibromocyclohexenediol, several C-2 Symmetrical building blocks were synthesized which gave access to D-myo-inositol 1,2,4,5-tetrakisphosphate and D-Myo-inositol 1,2,3,6-tetrakisphosphate. Exploiting the high regiospecificity of two partially purified phosphohydrolases from Dictyostelium, a 5-phosphatase and a phytase, the inositol tetrakisphosphates were converted enzymatically to the target compounds. Their potential to modulate the activity of Ins(3,4,5,6)P-4 I-kinase was investigated and compared with the effects Of D-myo-inositol 1,3,4-trisphosphate. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2705 / 2708

页数：4

共 11 条

[1] Enzyme-assisted total synthesis of the optical antipodes D-myo-inositol 3,4,5-trisphosphate and D-myo-inositol 1,5,6-trisphosphate:: Aspects of their structure -: Activity relationship to biologically active inositol phosphates [J].