Synthesis, structure, and biological evaluation of novel N- and O-linked diinositols.
Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested against several glycosidases (alpha- and beta-glucosidase, alpha- and beta-galactosidase, alpha- and beta-mannosidase) in an assay that measured the rate of hydrolysis of p-nitrophenolglycosides rather than the concentration of p-nitrophenolate. Somewhat surprisingly, the best inhibition was seen against beta-galactosidase with several of the compounds. The inositols linked through oxygen or nitrogen were subjected to calcium binding studies performed in NMR experiments. Detailed analysis of the title compounds by NMR spectroscopy has been performed, and full assignments were made. One of the attendant benefits of the preparation of these compounds has been expressed in the design and synthesis of new salen catalysts whose effectiveness has been compared with Jacobsen's catalyst in the epoxidation of styrene.
Paul
Bernhard J
BJ
University of Florida, Department of Chemistry, PO Box 117200, Gainesville, Florida 32611, USA.
Willis
Jerremey
J
Martinot
Theodore A
TA
Ghiviriga
Ion
I
Abboud
Khalil A
KA
Hudlicky
Tomas
T
D002118:Calcium / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004791:Enzyme Inhibitors; D007294:Inositol; D006026:Glycoside Hydrolases; D002118:Calcium