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Phenylglycine is the organic compound with the formula C 6 H 5 CH(NH 2)CO 2 H. It is a non-proteinogenic alpha amino acid related to alanine, but with a phenyl group in place of the methyl group. It is a white solid. The compound exhibits some biological activity. [1]
[2] [3] Upon treatment with base, the salt converts to glycine methyl ester. [4] Glycine methyl ester (and other esters of glycine) are not shelf-stable, tending to polymerize when stored at room temperature [4] or convert to diketopiperazine. The hydrochloride is shelf-stable.
Biosynthesis of HPG. HPG is synthesized from prephenate, an intermediate in the shikimic acid pathway and also a precursor to tyrosine.Prephenate is aromatized by prephenate dehydrogenase (Pdh) using NAD + as a cofactor to produce 4-hydroxyphenylpyruvate. 4-Hydroxyphenylpyruvate is then oxidized by 4-hydroxymandelate synthase (4HmaS) using oxygen to form 4-hydroxymandelate and hydrogen ...
2 H 3 N + CH 2 COO − → H 3 N + CH 2 CONHCH 2 COO − + H 2 O. Pyrolysis of glycine or glycylglycine gives 2,5-diketopiperazine, the cyclic diamide. [35] Glycine forms esters with alcohols. They are often isolated as their hydrochloride, such as glycine methyl ester hydrochloride. Otherwise, the free ester tends to convert to diketopiperazine.
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[1] [2] Azlactone chemistry: step 2 is a Perkin variation. 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.
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