Chloroalanine (3-chloroalanine) is an unnatural

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha ...

with the formula ClCH₂CH(NH₂)CO₂H. It is a white, water-soluble solid. The compound is usually derived from chlorination of

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α- amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − for ...

. The compound is used in the synthesis of other amino acids by replacement of the chloride. Protected forms of the related iodoalanine are also known.

Chemical properties

The

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

of 3-chloro-D-alanine is catalyzed by the enzyme

3-chloro-D-alanine dehydrochlorinase The enzyme 3-chloro-D-alanine dehydrochlorinase (EC 4.5.1.2) catalyzes the reaction : 3-chloro-D-alanine + H2O = pyruvate + chloride + NH3 (overall reaction) ::(1a) 3-chloro-D-alanine = chloride + 2-aminoprop-2-enoate ::(1b) 2-aminoprop-2-enoate ...

:{{cite journal , vauthors = Yamada H, Nagasawa T, Ohkishi H, Kawakami B, Tani Y , title = Synthesis of D-cysteine from 3-chloro-D-alanine and hydrogen sulfide by 3-chloro-D-alanine hydrogen chloride-lyase (deaminating) of Pseudomonas putida , journal = Biochemical and Biophysical Research Communications , volume = 100 , issue = 3 , pages = 1104–10 , date = June 1981 , pmid = 6791643 , doi = 10.1016/0006-291X(81)91937-9 :ClCH₂CH(NH₂)CO₂H + H₂O →CH₃C(O)CO₂H + NH₄Cl

References

Organochlorides Non-proteinogenic amino acids Amino acid derivatives