Loading AI tools
From Wikipedia, the free encyclopedia
The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone (also known as an azlactone).[1][2]
Hippuric acid, the benzamide derivative of glycine, cyclizes in the presence of acetic anhydride, condensing to give 2-phenyl-oxazolone.[3] This intermediate also has two acidic protons and reacts with benzaldehyde, acetic anhydride and sodium acetate to a so-called azlactone. This compound on reduction gives access to phenylalanine.[4]
Variants of the azlactone synthesis in which analogues of azlactones are used are sometimes advantageous. Hydantoin (in Bergmann modification), thiohydantoin and rhodanine have each been employed as the enolate-forming component of the condensation. [5][6] 2,5-Diketopiperazine can be used as a methylene component as well; its condensation products with aromatic aldehydes, on reduction and hydrolysis give the corresponding amino acids. [7][8][9]
In one study the Erlenmeyer amino acid synthesis was used in the heart of an L-m-tyrosine synthesis [10][11]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.