With methyl iodide, the amine becomes quaternized to give trimethylglycine, a natural product: With nitrous acid, one obtains glycolic acid ( van Slyke determination). With acid chlorides, glycine converts to the amidocarboxylic acid, such as hippuric acid and acetylglycine. Cu(H 2NCH 2CO 2) 2, which exists both in cis and trans isomers.

A typical complex is Cu(glycinate) 2, i.e. Glycine functions as a bidentate ligand for many metal ions, forming amino acid complexes. Above about 9.6, it converts to glycinate. In aqueous solution, glycine is amphoteric: below pH = 2.4, it converts to the ammonium cation called glycinium.

Its acid–base properties are most important. Glycine is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct. About 15 thousand tonnes are produced annually in this way. The two main processes are amination of chloroacetic acid with ammonia, giving glycine and ammonium chloride, and the Strecker amino acid synthesis, which is the main synthetic method in the United States and Japan. Production Īlthough glycine can be isolated from hydrolyzed protein, this route is not used for industrial production, as it can be manufactured more conveniently by chemical synthesis. In 1858, the French chemist Auguste Cahours determined that glycine was an amine of acetic acid. The name comes from the Greek word γλυκύς 'sweet tasting' (which is also related to the prefixes glyco- and gluco-, as in glycoprotein and glucose).

The American scientist Eben Norton Horsford, then a student of the German chemist Justus von Liebig, proposed the name 'glycocoll' however, the Swedish chemist Berzelius suggested the simpler name 'glycine'. He originally called it 'sugar of gelatin', but the French chemist Jean-Baptiste Boussingault showed that it contained nitrogen. Glycine was discovered in 1820 by the French chemist Henri Braconnot when he hydrolyzed gelatin by boiling it with sulfuric acid.

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