Please enable JavaScript.
Coggle requires JavaScript to display documents.
TAXOL : CHIRAL AUXILLARY CASE STUDY (ACTION (BINDS TO TUBULIN IN CELLS,…
TAXOL : CHIRAL AUXILLARY CASE STUDY
OPTICAL ISOMERISM
CHIRAL DRUGS EXIST IN 2 FORMS WITH DIFFERENT ACTIVITIES
THE WAY ENANTIOMERS BIND TO ACTIVE SITE CAUSES DIFFERENT BIOLOGICAL ACITIVITY
DRUGS IN RACEMIC MIXTURE FORM CAN HAVE UNWANTED CONSEQUENCES
THALIDOMIDE TRAGEDY
R FORM CAUSES THE DESIRED EFFECT OF INDUCING SLEEP
S FORM CAUSES DEFORMITIES IN FETUSES
DISCOVERY
ISOLATED FROM BARK OF PACIFIC YEW TREE
HUGE AMOUNT OF BARK NEEDED FOR VERY SMALL YIELD
SPARKED EFFORTS TO SYNTHESIZE THE COMPOUND
KILLS TREES
IDENTIFIED BY US NATIONAL CANCER INSTITUTE
APPROVED FOR THERAPEUTIC USE IN 1992
ACTION
BINDS TO TUBULIN IN CELLS
PREVENTS MICROTUBULES FROM BREAKING DOWN
HALTS CELL DIVISION CYCLE AND PREVENTS TUMOR
COMMONLY USE FOR OVARIAN AND BREAST CANCER
ASYMMETRIC SYNTHESIS
ISOLATING DESIRED ENANTIOMER FROM RACEMIC MIXTURE TOO IMPRACTICAL
CHIRAL AUXILLARY BINDS TO REACTANT TO PREVENT REACTION ON ONE SITE
REACTION IS FORCED TO PROCEED WITH SPECIFIED STEREOCHEMISTRY
TAKES 30 STEPS AND LOW YIELD
SEMI-SYNTHETIC SYNTHESIS DEVELOPED
SYNTHESIS STARTS WITH NATURAL PRECURSOR FROM COMPOUND IN NEEDLE OF YEW TREE IN EUROPE AND HIMALAYA
THE COMPOUND (10-DAB) CHEMICALLY MODIFIED TO FORM TAXOL
REQUIRES 13 SOLVENTS AND STILL HAVE A RELATIVELY LOW YIELD
ALTERNATIVES BEING EXPOLRED
TAXOL PRODUCING FUNGI
TAXOL EXTRACT FROM CULTURED PLANT CELLS AND PURIFIED THROUGH CHROMATOGRAPHY