D. PAVIA CHEM 425a/552

1. D. PAVIA CHEM 425a/552 NATURAL PRODUCTS CHEMISTRY THE OLIVE PROBLEM Crime scene investigators (CSI) frequently refer to the characteristic odor of a decomposing corpse. The characteristic smell is easily detected within a radius of about forty to fifty feet of the corpse. The odor largely arises from the hydrolysis of fats and proteins, which produce fatty acids and amino acids, respectively. The amino acids are further decomposed to small amines. You may recall that amines are often said to have a “dead-fish-like” odor. Two major contributors to this odor are the diamines putrescine ( H2N-CH2CH2CH2CH2-NH2 ) and cadaverine ( H2N-CH2CH2CH2CH2CH2-NH2 ) which are formed after hydrolysis when decarboxylase enzymes in bacteria work on: (1) an amino acid formed from decomposing (hydrolyzed) proteins and (2) a second amino acid intermediate from the urea cycle which is not involved in the formation of proteins. 1. Which specific amino acids produce putrescine and cadaverine respectively? Draw their structures and name them. 2. What coenzyme is responsible for the production of the diamines? 3. Draw a complete mechanism for the production of putrescine from its parent amino acid. 4. Which of the two parent amino acids is not used in the formation of proteins and is not encoded in the genetic code? __________ 5. Extra credit if you can give a possible chemical reason for the fact stated in Question 4.