Chloroalanine

Chloroalanine (3-chloroalanine) is an unnatural amino acid with the formula ClCH₂CH(NH₂)CO₂H. It is a white, water-soluble solid. The compound is usually derived from chlorination of serine. The compound is used in the synthesis of other amino acids by replacement of the chloride.^[1] Protected forms of the related iodoalanine are also known.^[2][3]

Chloroalanine

3-Chloro-L-alanine
Names
Other names 3-Chloroalanine 2-Amino-3-chloropropanoic acid
Identifiers
CAS Number	2731-73-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:88164
ChemSpider	77
PubChem CID	78
UNII	75RTT737SY Y
CompTox Dashboard (EPA)	DTXSID70927558
InChI InChI=1S/C3H6ClNO2/c4-1-2(5)3(6)7/h2H,1,5H2,(H,6,7) Key: ASBJGPTTYPEMLP-UHFFFAOYSA-N
SMILES C(C(C(=O)O)N)Cl
Properties
Chemical formula	C3H6ClNO2
Molar mass	123.54 g·mol−1
Appearance	White solid
Melting point	166–167 °C (331–333 °F; 439–440 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical properties

The hydrolysis of 3-chloro-D-alanine is catalyzed by the enzyme 3-chloro-D-alanine dehydrochlorinase:^[4]

ClCH₂CH(NH₂)CO₂H + H₂O →CH₃C(O)CO₂H + NH₄Cl