Synthesis of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

Kevin R H Solomons; Sally Freeman; Carl H. Schwalbe; Stephen B. Shears; Deborah J. Nelson; Weiwen Xie; Karol S. Bruzik; Marcia A. Kaetzel

doi:10.1016/S0008-6215(98)00146-3

Synthesis of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

Kevin R H Solomons, Sally Freeman, Carl H. Schwalbe, Stephen B. Shears, Deborah J. Nelson, Weiwen Xie, Karol S. Bruzik, Marcia A. Kaetzel

Research output: Contribution to journal › Article › peer-review

Abstract

DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. Copyright (C) 1998 Elsevier Science Ltd.

Original language	English
Pages (from-to)	337-343
Number of pages	6
Journal	Carbohydrate Research
Volume	309
Issue number	4
DOIs	https://doi.org/10.1016/S0008-6215(98)00146-3
Publication status	Published - Jun 1998

Keywords

Chloride current
Crystal structure
Inositol polyphosphates
Myo-inositol 3,4,5,6-tetrakisphosphate

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10.1016/S0008-6215(98)00146-3

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@article{95f7312b152a4f1db9acc95ad2a99cb5,

title = "Synthesis of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate",

abstract = "DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. Copyright (C) 1998 Elsevier Science Ltd.",

keywords = "Chloride current, Crystal structure, Inositol polyphosphates, Myo-inositol 3,4,5,6-tetrakisphosphate",

author = "Solomons, {Kevin R H} and Sally Freeman and Schwalbe, {Carl H.} and Shears, {Stephen B.} and Nelson, {Deborah J.} and Weiwen Xie and Bruzik, {Karol S.} and Kaetzel, {Marcia A.}",

year = "1998",

month = jun,

doi = "10.1016/S0008-6215(98)00146-3",

language = "English",

volume = "309",

pages = "337--343",

journal = "Carbohydrate Research",

issn = "1873-426X",

publisher = "Elsevier BV",

number = "4",

}

TY - JOUR

T1 - Synthesis of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

AU - Solomons, Kevin R H

AU - Freeman, Sally

AU - Schwalbe, Carl H.

AU - Shears, Stephen B.

AU - Nelson, Deborah J.

AU - Xie, Weiwen

AU - Bruzik, Karol S.

AU - Kaetzel, Marcia A.

PY - 1998/6

Y1 - 1998/6

N2 - DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. Copyright (C) 1998 Elsevier Science Ltd.

AB - DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. Copyright (C) 1998 Elsevier Science Ltd.

KW - Chloride current

KW - Crystal structure

KW - Inositol polyphosphates

KW - Myo-inositol 3,4,5,6-tetrakisphosphate

U2 - 10.1016/S0008-6215(98)00146-3

DO - 10.1016/S0008-6215(98)00146-3

M3 - Article

SN - 1873-426X

VL - 309

SP - 337

EP - 343

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 4

ER -

Synthesis of D-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

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Keywords

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