Phenylglycine is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C
6H
5CH(NH
2)CO
2H. It is a
non-proteinogenic alpha amino acid related to
alanine
Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side ...
, but with a
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...
group in place of the
methyl group. It is a white solid. The compound exhibits some
biological activity.
Preparation
It is prepared from
benzaldehyde by amino cyanation (
Strecker synthesis
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide. The condensation reaction yields an α- ...
).
It can also be prepared from
glyoxal
Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...
and by
reductive amination
Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...
of
phenylglyoxylic acid.
Ester
The ester methyl α‐phenylglycinate is used to convert
carboxylic acids into homologated unsaturated ketones. These reactions proceed via cyclization of phenylglycinamides to
oxazolones, which can be reductively cleaved with chromous reagents.
[{{cite encyclopedia
, title=Methyl α‐Phenylglycinate
, authors=Wolfgang Steglich Stefan Jaroch
, year=2001
, doi=10.1002/047084289X.rm229
, encyclopedia=Encyclopedia of Reagents for Organic Synthesis, chapter=Methyl α-Phenylglycinate
, isbn=0471936235
]
See also
*
''N''-Phenylglycine
*
(RS)-MCPG
References
Amino acids