Question
At the beginning of the Gabriel synthesis, a ____ is
protected in a phthalimide (analogous to a di-amide) to prevent more than one
alkylation from occurring.
Answer
At the beginning of the Gabriel synthesis, a nitrogen is
protected in a phthalimide (analogous to a di-amide) to prevent more than one
alkylation from occurring.
Definition: De Novo means 'starting from the beginning'.
Note: As seen below, the final product has the classic amino acid groups. Amino acid is generated from phthalimide (nucleophile) and diethyl bromomalonate, using two SN2 reactions, hydrolysis, and decarboxylation.
Note: In Strecker synthesis, first an aminonitrile is generate from an aldehyde or ketone. Secondly, hydrolysis of the aminonitrile results in formation of an amino acid.
Note: The starting material for the Strecker synthesis is a planar carbonyl-containing compound; therefore, the product of this pathway is a racemic mixture. The incoming nucleophiles are equally able to attack from either side of the carbonyl; thus, both L- and D-amino acids can be generated through this process.
Question: What are the two ways we can organically synthesize amino acids?
1. Strecker Synthesis (Strecker uses Cyanide)
2. Gabriel Synthesis (Gabriel uses Rings)
Extra Note: The product of both the Strecker and the Gabriel synthesis pathways is a racemic mixture; both L- and D- amino acids are generated.
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