Spirophostins: conformationally restricted analogues of adenophostin A |
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Authors: | de Kort M Regenbogen A D Valentijn A R Challiss R A Iwata Y Miyamoto S van der Marel G A van Boom J H |
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Institution: | Leiden Institute of Chemistry, Gorlaeus Laboratories Leiden University, The Netherlands. |
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Abstract: | The synthesis, biological evaluation, and molecular modeling of two conformationally restricted analogues of adenophostinA (1), denominated as spirophostin (3R)-10 and (3S)-11, as novel ligands for the D-myo-inositol 1,4,5-trisphosphate receptor (IP3R), is presented. These diastereoisomeric spiroketals are synthesized by spiroketalization of D-glucose derivatives (2S)-15 and (2R)-16, separation of the protected isomers (3R)-19 and (3S)-20, followed by phosphorylation and deprotection. The spirophostins (3R)-10 and (3S)-11 display comparable biological activity, with a 3H-IP3-displacing and Ca2+-releasing potency less than IP3 and adenophostin A. |
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