Chloroalanine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Chloroalanine
3-Chloro-L-alanine
Names
Other names
  • 3-Chloroalanine
  • 2-Amino-3-chloropropanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C3H6ClNO2/c4-1-2(5)3(6)7/h2H,1,5H2,(H,6,7)
    Key: ASBJGPTTYPEMLP-UHFFFAOYSA-N
  • C(C(C(=O)O)N)Cl
Properties
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:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).
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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

References

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