PHAR1026 - Pharmaceutical And Biological Chemistry Assignment

Assignment Task

Questions 

1. State how many chiral centres are present in and assign the configurations of the chiral carbon atoms labelled A in lincomycin and in clindamycin. Show the priorities assigned to the groups in establishing these configurations. 

2. Assign the geometry of the alkene function in compound. Show the priorities assigned to the groups in establishing the geometry.

3. State which of the following functional groups are present in lincomycin: alcohol, aldehyde, amide, anhydride, carboxylic acid, ester, lactam, ketone, phenol, thioether. One or more terms may apply; marks will be deducted for incorrect answers, with a minimum mark of zero possible.

4. Draw lincomycin in the form of a Newman projection looking down the bond that connects carbon atoms labelled A and B. In your drawings, abbreviate as R and R’ the substituents containing the remainder of the lincomycin molecule.

5. When reaction is repeated in the presence of NaOMe, product is formed. Provide a mechanism describing the formation of compound  under these conditions.

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