De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation

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OriginalspracheEnglisch
Seiten (von - bis)1057-1061
Seitenumfang5
FachzeitschriftTetrahedron Asymmetry
Jahrgang11
Ausgabenummer5
PublikationsstatusVeröffentlicht - 24 März 2000
Extern publiziertJa

Abstract

The first total synthesis of Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4 is presented. Starting from p-benzoquinone, we took advantage of the C2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP3 isomers were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P3, Ins(2,3,6)P3 and Ins(1,2,4)P3. Copyright (C) 2000 Elsevier Science Ltd.

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De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation. / Plettenburg, O.; Adelt, S.; Vogel, G. et al.
in: Tetrahedron Asymmetry, Jahrgang 11, Nr. 5, 24.03.2000, S. 1057-1061.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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title = "De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation",
abstract = "The first total synthesis of Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4 is presented. Starting from p-benzoquinone, we took advantage of the C2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP3 isomers were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P3, Ins(2,3,6)P3 and Ins(1,2,4)P3. Copyright (C) 2000 Elsevier Science Ltd.",
author = "O. Plettenburg and S. Adelt and G. Vogel and Altenbach, {H. J.}",
note = "Funding Information: We are grateful to Dr. W. V. Turner for stimulating discussions and critical reading of the manuscript. This work was supported by the Deutsche Forschungsgemeinschaft (grant VO 348/2-2) and the Fonds der Chemischen Industrie.",
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TY - JOUR

T1 - De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation

AU - Plettenburg, O.

AU - Adelt, S.

AU - Vogel, G.

AU - Altenbach, H. J.

N1 - Funding Information: We are grateful to Dr. W. V. Turner for stimulating discussions and critical reading of the manuscript. This work was supported by the Deutsche Forschungsgemeinschaft (grant VO 348/2-2) and the Fonds der Chemischen Industrie.

PY - 2000/3/24

Y1 - 2000/3/24

N2 - The first total synthesis of Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4 is presented. Starting from p-benzoquinone, we took advantage of the C2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP3 isomers were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P3, Ins(2,3,6)P3 and Ins(1,2,4)P3. Copyright (C) 2000 Elsevier Science Ltd.

AB - The first total synthesis of Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4 is presented. Starting from p-benzoquinone, we took advantage of the C2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP3 isomers were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P3, Ins(2,3,6)P3 and Ins(1,2,4)P3. Copyright (C) 2000 Elsevier Science Ltd.

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U2 - 10.1016/S0957-4166(00)00063-X

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SP - 1057

EP - 1061

JO - Tetrahedron Asymmetry

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