Question

11. The bowhead whale, which has a large head that is up to 40% of its body length, lives in the Arctic. The age of the bowhead whale is estimated by measuring the extent to which the amino acid Asp (aspartic acid), which is found in the eyes of the whales, has undergone racemization. For example, 100% of (L.) aspartic acid racemizes towards a more 50:50 mixture of (L) and (D-aspartic acid Provide a complete, stepwise, curved-arrow mechanism for the acid-catalyzed transformation of (L) aspartic acid to (D)-aspartic acid. Draw the best resonance contributor for each proposed intermediate. Use H-B* to represent an acid and B for its conjugate base. НО. H-B HO тон OH HNH HEN HO OH OHN HO. ОН 21

Answer 1

Но. HB Chirality lost. ОН о н, N но. HBH ОН 1 NH 3 intermediate Оң Ръри Туари но Сң NH₂ HBH 애 ИО, froton NH₂ о H Transfer 애 НО T BH о Chisality regain