CP Flashcards
Distinguish the six-membered ring from the seven-membered ring
A six membered ring contains six “members” including the oxygen. In this case the chair conofrmamtion, is a six memebred ring.
A seven membered ring contains seven “members” including the oxygen. In this case the the structure highlighted in yellow.
What is an epoxide?
Epoxides are cyclic ethers involving one oxygen and two carbons in a three membered ring.
Describe the reactivity of an epoxide.
Epoxides suffer from ring strain and tehrefore are highly reactive and susceptible to nucleophilic attack
Describe the reaction of an expoxide ring opening when you have a weak nucleophile vs a strong nucleophile
Strong nucleophiles react at the less substituted position, while
Weak nucleophiles react at the more substituted position (3o carbons)
What would be the products of this reaction? Draw out indicating stereochemsitry
m-CPBA is a reagent most often used when..
an alkene is turning into an epoxide. It stands for meta-chloroperoxybenzoic acid.
What can anomeric carbons be classified as ?
Epimers
What are the two amino acids with a carboxylic acid group in their structure?
Glutamate and Aspartate
What is a prodrug and how do they work?
Prodrugs are drugs you take that once in the body have to go through a chemical conversion transforming them from INACTIVE to ACTIVE.
What are the two condtions for a compoound (ex. phenazonapthol glycoside) being an effective prodrug? What is one way to experimentally determine its an effective prodrug.
- The drug needs to be combined with the compound/molecule’s moiety, in this case phenazonapthol glycoside to form a drug-phenazonapthol compound.
- The molecule is cleaved into its active form.
You can use UV spectroscopy to distinguish the cleaved and uncleaved forms of the prodrug.
What are the four amino acids with aromatic side chains?
Tyrosine, Phenylalanine, Tryptophan and Histidine
What is the structure of histidine?
Histidine has an ionizable imidazole ring that is aromatic
