Chloroalanine

Chloroalanine
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 ;
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

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]

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

Hondal, Robert J.; Nilsson, Bradley L.; Raines, Ronald T. (2001). "Selenocysteine in Native Chemical Ligation and Expressed Protein Ligation". Journal of the American Chemical Society. 123 (21): 5140–5141. doi:10.1021/ja005885t. PMID 11457362.
Richard F. W. Jackson; Manuel Perez-Gonzalez (2005). "Synthesis of N-(Tert-butoxycarbonyl)-β-iodoalanine Methyl Ester: A Useful Building Block in the Synthesis of Nonnatural α-amino Acids via Palladium Catalyzed Cross Coupling Reactions". Org. Synth. 81: 77. doi:10.15227/orgsyn.081.0077.
Atmuri, N. D. P.; Lubell, W. D. (2015). "Preparation of N-(Boc)-Allylglycine Methyl Ester Using a Zinc-mediated, Palladium-catalyzed Cross-coupling Reaction". Org. Synth. 92: 103. doi:10.15227/orgsyn.092.0103.
Yamada H, Nagasawa T, Ohkishi H, Kawakami B, Tani Y (June 1981). "Synthesis of D-cysteine from 3-chloro-D-alanine and hydrogen sulfide by 3-chloro-D-alanine hydrogen chloride-lyase (deaminating) of Pseudomonas putida". Biochemical and Biophysical Research Communications. 100 (3): 1104–10. doi:10.1016/0006-291X(81)91937-9. PMID 6791643.

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[1] Hondal, Robert J.; Nilsson, Bradley L.; Raines, Ronald T. (2001). "Selenocysteine in Native Chemical Ligation and Expressed Protein Ligation". Journal of the American Chemical Society. 123 (21): 5140–5141. doi:10.1021/ja005885t. PMID 11457362.

[2] Richard F. W. Jackson; Manuel Perez-Gonzalez (2005). "Synthesis of N-(Tert-butoxycarbonyl)-β-iodoalanine Methyl Ester: A Useful Building Block in the Synthesis of Nonnatural α-amino Acids via Palladium Catalyzed Cross Coupling Reactions". Org. Synth. 81: 77. doi:10.15227/orgsyn.081.0077.

[3] Atmuri, N. D. P.; Lubell, W. D. (2015). "Preparation of N-(Boc)-Allylglycine Methyl Ester Using a Zinc-mediated, Palladium-catalyzed Cross-coupling Reaction". Org. Synth. 92: 103. doi:10.15227/orgsyn.092.0103.

[4] Yamada H, Nagasawa T, Ohkishi H, Kawakami B, Tani Y (June 1981). "Synthesis of D-cysteine from 3-chloro-D-alanine and hydrogen sulfide by 3-chloro-D-alanine hydrogen chloride-lyase (deaminating) of Pseudomonas putida". Biochemical and Biophysical Research Communications. 100 (3): 1104–10. doi:10.1016/0006-291X(81)91937-9. PMID 6791643.