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anyone can help me with it...? bioanalytical Quinine and quinidine (CzoHaNO)2 al

ID: 181952 • Letter: A

Question

anyone can help me with it...? bioanalytical

Quinine and quinidine (CzoHaNO)2 alkaloids extracted from the Cinchona bark are isomers but their action is quite different: quinine is an antimalarial while quinidine is an antiarrhythmic agent. About 50 % of the production of quinine is used for its bitter taste in drinks (tonic water, bitter lemon..). Cinchonine and cinchonidine (CuH2N O) are alkaloids also from Cinchona, related to quinidine and quinine, respectively quinine cinchonidine R-H quinidine R-OCH, cinchonine R H HO HO Question 1 (2 pts) Quinine has many chiral carbons: a) b) What is the definition of a chiral carbon ? What is the absolute configuration of carbons (8) and (2) in quinine and quinidine? (It is important to explain how you arrive at the result) Question 2 (2 pts) Quinine has 2 basic nitrogen atoms. (The 2 pKa values are indicated in the figure at the right.) a) Write the ladder diagram, of quinine as a function of pH b) What is the structure of quinine in plasma ? c) What is the best pll range for extracting quinine in an DK1 5.0 organic solvent ? 0 What is the percentage of quinine base in an aqueous solution at plH- 12.7? Question 3 (2 pts) (t is preferable to do 02 first) Patent WO 2011161691Al describes a method for preparing quinine hydrochloride,

Explanation / Answer

Q. 1. (a) An asymmetric carbon atom (also known as chiral carbon) is a carbon atom that is attached to four different types of atoms or groups of atoms.

(b)