Strecker Synthesis of Amino Acids 2

Strecker Synthesis of Amino Acids 2 - H 2 N H N H H 2 N H N...

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Strecker Synthesis of Amino Acids The Strecker synthesis of α -amino acids (dating back to 1850) involves a reaction between an aldehyde, ammonia, and cyanide anion. The cyanide is ultimately hydrolyzed to the carboxylic acid. Consecutive mechanisms: 1. Imine formation. 2. Cyanide attack on “carbonyl carbon” of the iminimum ion. 3. Acid catalyzed hydrolysis of the nitrile (cyanide). H O + H H O H O H H CN H 2 N H Imine formation followed by protonation Attack of cyanide nucleophile (S N 2 reaction) Acid Catalyzed hydrolysis of the Nitrile (cyanide)
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Unformatted text preview: H 2 N H N H H 2 N H N H OH 2 H 2 N H N H OH 2 H 2 N H N H OH 2 PS H 2 N H N H 2 OH H 2 N H N H 2 OH H 2 N H N H 2 OH OH 2 H 2 N H H 2 N OH OH 2 PS H 2 N H H 3 N OH OH- NH 3 H 2 N H O OH H- H H 2 N H O OH NH 3 NH 3 H O H PS NH 2 H 2 O H- H 2 O N H H N H H + CN Why do we care about this? Because -amino acids are the building blocks of all proteins in little bacteria, jumbo blue whales, and you and me. Although this method was invented over 150 years ago, it is still used today to make amino acids....
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This note was uploaded on 09/25/2009 for the course CH 223 taught by Professor Brown during the Spring '08 term at N.C. State.

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