Synthesis of 4-C-alkyl inositol 1,4,5-trisphosphates and 1,3,4,5-tetrakisphosphates.
The preparation of 2,3,6-O-tribenzyl- and 2,6-O-dibenzyl-myo-inositols with beta-primary, secondary, and tertiary 4-C-alkyl or aryl groups is reported. Five of these novel polyols are elaborated to 4-C-alkyl Ins(1,4,5)P(3) and Ins(1,3,4,5)P(4) analogues. Regio- and stereoselective introduction of 4-C-alkyl or aryl substituents proceeded via a 4-exo-methylene oxide. Subsequent regioselective reduction of an orthobenzoate provided a divergent method to access both InsP(3) and InsP(4) precursors. Previously unreported phosphorylation of the tertiary hydroxyl and global deprotection afforded novel analogues that retain their full complement of polar and charged binding features.
Swarbrick
Joanna M
JM
Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK.
Gaffney
Piers R J
PR
D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D009943:Organophosphorus Compounds; D015544:Inositol 1,4,5-Trisphosphate