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C9033

Sigma-Aldrich

β-Chloro-L-alanine hydrochloride

Alanine aminotransferase inhibitor

Synonym(s):

(R)-2-Amino-3-chloropropanoic acid, 3-Chloro-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C3H6ClNO2 · HCl
CAS Number:
51887-89-9
Molecular Weight:
160.00
MDL number:
MFCD00070398
UNSPSC Code:
12352204
PubChem Substance ID:
24278345
NACRES:
NA.32

biological source

synthetic

assay

≥98% (TLC)

form

powder

mp

205 °C

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl[H].N[C@@H](CCl)C(O)=O

InChI

1S/C3H6ClNO2.ClH/c4-1-2(5)3(6)7;/h2H,1,5H2,(H,6,7);1H/t2-;/m0./s1

InChI key

IENJPSDBNBGIEL-DKWTVANSSA-N

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Application

β-Chloro-L-alanine hydrochloride has been used:
  • as a substrate for screening tyrosine phenol lyase steady state kinetics
  • in the inhibition of serine palmitoyltransferase and cytotoxicity studies in lymphocyte Ly-1 cells
  • as an inhibitor of alanine transaminase in wheat germ cell-free protein synthesis system

Biochem/physiol Actions

β-Chloro-L-alanine hydrochloride is an inhibitor of alanine aminotransferase (ALAT). Inhibition of ALAT leads to suppression of tumor progression in lung carcinoma.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Serine 51 residue of Citrobacter freundii tyrosine phenol-lyase assists in C-alpha-proton abstraction and transfer in the reaction with substrate
Barbolina MV, et al.
Biochimie, 147(1), 63-69 (2018)
Oxytetracycline have the therapeutic efficiency in CD133+ HCC population through suppression CD133 expression by decreasing of protein stability of CD133
Song Y, et al.
Scientific Reports, 8(1), 16100-16100 (2018)
Specificity of inhibitors of serine palmitoyltransferase (SPT), a key enzyme in sphingolipid biosynthesis, in intact cells: a novel evaluation system using an SPT-defective mammalian cell mutant
Hanada K, et al.
Biochemical Pharmacology, 59(10), 1211-1216 (2000)
A novel way of amino acid-specific assignment in 1 H-15 N HSQC spectra with a wheat germ cell-free protein synthesis system
Morita EH, et al.
Journal of Biomolecular Nmr, 30(1), 37-45 (2004)
Inhibition of alanine aminotransferase (ALAT) in silico and in vivo promotes mitochondrial metabolism to impair malignant growth
Beuster G, et al.
The Journal of Biological Chemistry, jbc-M110 (2011)
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