Synthesis of cyclic adenosine 5'-diphosphate ribose analogues: a C2'endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor.

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Synthesis of cyclic adenosine 5'-diphosphate ribose analogues: a C2'endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor. / Moreau, Christelle; Ashamu, Gloria A; Bailey, Victoria C; Galione, Antony; Guse, Andreas H.; Potter, Barry V L.

in: ORG BIOMOL CHEM, Jahrgang 9, Nr. 1, 1, 2011, S. 278-290.

Publikationen: SCORING: Beitrag in Fachzeitschrift/ZeitungSCORING: ZeitschriftenaufsatzForschungBegutachtung

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@article{5c84652b90d4470aafbe421d0e761c65,
title = "Synthesis of cyclic adenosine 5'-diphosphate ribose analogues: a C2'endo/syn {"}southern{"} ribose conformation underlies activity at the sea urchin cADPR receptor.",
abstract = "Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5'-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by (1)H NMR spectroscopy revealed that a C2'endo/syn conformation of the {"}southern{"} ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.",
keywords = "Animals, Models, Molecular, Calcium/metabolism, Molecular Conformation, Aplysia/enzymology, Cyclic ADP-Ribose/analogs & derivatives/*chemical synthesis, Receptors, Purinergic P1/*metabolism, Ribose/*chemistry, Sea Urchins/*metabolism, Animals, Models, Molecular, Calcium/metabolism, Molecular Conformation, Aplysia/enzymology, Cyclic ADP-Ribose/analogs & derivatives/*chemical synthesis, Receptors, Purinergic P1/*metabolism, Ribose/*chemistry, Sea Urchins/*metabolism",
author = "Christelle Moreau and Ashamu, {Gloria A} and Bailey, {Victoria C} and Antony Galione and Guse, {Andreas H.} and Potter, {Barry V L}",
year = "2011",
language = "English",
volume = "9",
pages = "278--290",
number = "1",

}

RIS

TY - JOUR

T1 - Synthesis of cyclic adenosine 5'-diphosphate ribose analogues: a C2'endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor.

AU - Moreau, Christelle

AU - Ashamu, Gloria A

AU - Bailey, Victoria C

AU - Galione, Antony

AU - Guse, Andreas H.

AU - Potter, Barry V L

PY - 2011

Y1 - 2011

N2 - Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5'-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by (1)H NMR spectroscopy revealed that a C2'endo/syn conformation of the "southern" ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.

AB - Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5'-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by (1)H NMR spectroscopy revealed that a C2'endo/syn conformation of the "southern" ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.

KW - Animals

KW - Models, Molecular

KW - Calcium/metabolism

KW - Molecular Conformation

KW - Aplysia/enzymology

KW - Cyclic ADP-Ribose/analogs & derivatives/chemical synthesis

KW - Receptors, Purinergic P1/metabolism

KW - Ribose/chemistry

KW - Sea Urchins/metabolism

KW - Animals

KW - Models, Molecular

KW - Calcium/metabolism

KW - Molecular Conformation

KW - Aplysia/enzymology

KW - Cyclic ADP-Ribose/analogs & derivatives/chemical synthesis

KW - Receptors, Purinergic P1/metabolism

KW - Ribose/chemistry

KW - Sea Urchins/metabolism

M3 - SCORING: Journal article

VL - 9

SP - 278

EP - 290

IS - 1

M1 - 1

ER -