A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate

Neil S. Keddie; Geert Bultynck; Tomas Luyten; Alexandra M. Z. Slawin; Stuart J. Conway

doi:10.1016/j.tetasy.2009.03.006

A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate

Neil S. Keddie, Geert Bultynck, Tomas Luyten, Alexandra M. Z. Slawin, Stuart J. Conway

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

Abstract

The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	857-866
Number of pages	10
Journal	Tetrahedron: Asymmetry
Volume	20
Issue number	6-8
Early online date	1 Apr 2009
DOIs	https://doi.org/10.1016/j.tetasy.2009.03.006
Publication status	Published - 7 May 2009

Keywords

Catalytic Asymmetric Phosphorylation
Pure Natural Inositols
Enantiomerically Pure
Adenophostin-A
Myoinositol 1,4,5-Trisphosphate
Penicillium-Brevicompactum
Trisphosphate Receptors
Expeditious Route
Potent Agonists
D-Galactose

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10.1016/j.tetasy.2009.03.006

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title = "A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate",

abstract = "The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "Catalytic Asymmetric Phosphorylation, Pure Natural Inositols, Enantiomerically Pure, Adenophostin-A, Myoinositol 1,4,5-Trisphosphate, Penicillium-Brevicompactum, Trisphosphate Receptors, Expeditious Route, Potent Agonists, D-Galactose",

author = "Keddie, \{Neil S.\} and Geert Bultynck and Tomas Luyten and Slawin, \{Alexandra M. Z.\} and Conway, \{Stuart J.\}",

note = "This work is partially supported by BBSRC UK.",

year = "2009",

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doi = "10.1016/j.tetasy.2009.03.006",

language = "English",

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T1 - A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate

AU - Keddie, Neil S.

AU - Bultynck, Geert

AU - Luyten, Tomas

AU - Slawin, Alexandra M. Z.

AU - Conway, Stuart J.

N1 - This work is partially supported by BBSRC UK.

PY - 2009/5/7

Y1 - 2009/5/7

N2 - The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

AB - The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

KW - Catalytic Asymmetric Phosphorylation

KW - Pure Natural Inositols

KW - Enantiomerically Pure

KW - Adenophostin-A

KW - Myoinositol 1,4,5-Trisphosphate

KW - Penicillium-Brevicompactum

KW - Trisphosphate Receptors

KW - Expeditious Route

KW - Potent Agonists

KW - D-Galactose

UR - https://www.scopus.com/pages/publications/65549140099

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DO - 10.1016/j.tetasy.2009.03.006

M3 - Article

SN - 0957-4166

VL - 20

SP - 857

EP - 866

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 6-8

ER -

A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate

Abstract

Keywords

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