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/Zeitung › SCORING: Zeitschriftenaufsatz › Forschung › Begutachtung
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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 -