Streckersynteesi

Strecker synthesis is a method for synthesizing alpha-amino acids. It was first reported by the German chemist Adolph Strecker in 1850. The reaction typically involves the treatment of an aldehyde or ketone with ammonia and hydrogen cyanide, followed by hydrolysis of the resulting alpha-aminonitrile. The overall process effectively converts a carbonyl compound into an amino acid with the same carbon skeleton.

The first step of the Strecker synthesis involves the reaction of an aldehyde or ketone with ammonia to form an imine. This imine then reacts with hydrogen cyanide, usually generated in situ from a cyanide salt and an acid, to produce an alpha-aminonitrile. The final step is the hydrolysis of the nitrile group to a carboxylic acid, yielding the alpha-amino acid. This hydrolysis can be achieved under either acidic or basic conditions.

The Strecker synthesis is a versatile method that can be used to prepare a wide variety of alpha-amino acids, including both natural and unnatural ones. It is particularly useful for synthesizing amino acids with non-polar side chains. However, the method can also be applied to aldehydes and ketones bearing polar or reactive functional groups, provided appropriate protective group strategies are employed. The reaction is generally carried out at room temperature or with gentle heating. A key advantage of the Strecker synthesis is its relatively straightforward procedure and the availability of starting materials.