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Chemical Compound Review

AGN-PC-00D00B     2-amino-3-chloro-propanoic acid

Synonyms: AG-D-65332, ACMC-20a5m2, NSC-337715, AC1Q3TUM, KB-47957, ...
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Disease relevance of beta-Chloro-L-alanine


High impact information on beta-Chloro-L-alanine


Chemical compound and disease context of beta-Chloro-L-alanine


Biological context of beta-Chloro-L-alanine

  • Collagen fragmentation by HOCl, inhibition of gelation by HOCl, and N-chloroalanine-induced proteolytic susceptibility, all increased with linear kinetics at oxidant concentrations of 5 microM to 1.0 mM [14].
  • BCA inhibited 75% of the [(3)H]thymidine incorporation, and the cells were arrested before the S phase of the cell cycle [15].
  • Two spontaneous mutants of lambda dilv-lac11 that have high-level constitutive expression of the ilv-lac fusion operon were isolated by growth on a beta-chloroalanine selective medium [16].
  • The effects of fumonisin on cell growth and cell death were only partially prevented by beta-chloroalanine (approximately 50 to 60%) [17].

Anatomical context of beta-Chloro-L-alanine


Associations of beta-Chloro-L-alanine with other chemical compounds


Gene context of beta-Chloro-L-alanine


Analytical, diagnostic and therapeutic context of beta-Chloro-L-alanine


  1. Mechanism-based inactivation of bacterial kynureninase by beta-substituted amino acids. Kishore, G.M. J. Biol. Chem. (1984) [Pubmed]
  2. Active transport in Escherichia coli B membrane vesicles. Differential inactivating effects from the enzymatic oxidation of beta-chloro-L-alanine and beta-chloro-D-alanine. Kaczorowski, G., Shaw, L., Laura, R., Walsh, C. J. Biol. Chem. (1975) [Pubmed]
  3. Synergic activity of D-cycloserine and beta-chloro-D-alanine against Mycobacterium tuberculosis. David, S. J. Antimicrob. Chemother. (2001) [Pubmed]
  4. Activation of the de novo biosynthesis of sphingolipids mediates angiotensin II type 2 receptor-induced apoptosis. Lehtonen, J.Y., Horiuchi, M., Daviet, L., Akishita, M., Dzau, V.J. J. Biol. Chem. (1999) [Pubmed]
  5. Monoclonal antibodies against Nalpha-(5'-phosphopyridoxyl)-L-lysine. Screening and spectrum of pyridoxal 5'-phosphate-dependent activities toward amino acids. Gramatikova, S.I., Christen, P. J. Biol. Chem. (1997) [Pubmed]
  6. Mechanism of mutual activation of the tryptophan synthase alpha and beta subunits. Analysis of the reaction specificity and substrate-induced inactivation of active site and tunnel mutants of the beta subunit. Ahmed, S.A., Ruvinov, S.B., Kayastha, A.M., Miles, E.W. J. Biol. Chem. (1991) [Pubmed]
  7. Chemical structure of the active site of pig heart mitochondrial aspartate aminotransferase labeled with beta-chloro-l-alanine. Morino, Y., Tanase, S. J. Biol. Chem. (1978) [Pubmed]
  8. Coupling of alanine racemase and D-alanine dehydrogenase to active transport of amino acids in Escherichia coli B membrane vesicles. Kaczorowski, G., Shaw, L., F-entes, M., Walsh, C. J. Biol. Chem. (1975) [Pubmed]
  9. beta-Chloro-L-alanine inhibition of the Escherichia coli alanine-valine transaminase. Whalen, W.A., Wang, M.D., Berg, C.M. J. Bacteriol. (1985) [Pubmed]
  10. Synthesis of D-cysteine-related amino acids by 3-chloro-D-alanine chloride-lyase of Pseudomonas putida CR 1-1. Nagasawa, T., Hosono, H., Ohkishi, H., Tani, Y., Yamada, H. Biochem. Biophys. Res. Commun. (1983) [Pubmed]
  11. Properties, sequence, and synthesis in Escherichia coli of 1-aminocyclopropane-1-carboxylate deaminase from Hansenula saturnus. Minami, R., Uchiyama, K., Murakami, T., Kawai, J., Mikami, K., Yamada, T., Yokoi, D., Ito, H., Matsui, H., Honma, M. J. Biochem. (1998) [Pubmed]
  12. Inhibition of uridine 5'-diphosphate-N-acetylmuramyl-L-alanine synthetase by beta-chloro-L-alanine in Escherichia coli. Ishiguro, E.E. Can. J. Microbiol. (1982) [Pubmed]
  13. Synthesis of S-(carboxymethyl)-D-cysteine by 3-chloro-D-alanine chloride-lyase of pseudomonas putida CR 1-1. Nagasawa, T., Hosono, H., Ohkishi, H., Yamada, H. Appl. Biochem. Biotechnol. (1983) [Pubmed]
  14. Potential roles of hypochlorous acid and N-chloroamines in collagen breakdown by phagocytic cells in synovitis. Davies, J.M., Horwitz, D.A., Davies, K.J. Free Radic. Biol. Med. (1993) [Pubmed]
  15. Diacylglycerol generated during sphingomyelin synthesis is involved in protein kinase C activation and cell proliferation in Madin-Darby canine kidney cells. Cerbón, J., del Carmen López-Sánchez, R. Biochem. J. (2003) [Pubmed]
  16. Isolation and analysis of two Escherichia coli K-12 ilv attenuator deletion mutants with high-level constitutive expression of an ilv-lac fusion operon. Bennett, D.C., Umbarger, H.E. J. Bacteriol. (1984) [Pubmed]
  17. Elevated sphingoid bases and complex sphingolipid depletion as contributing factors in fumonisin-induced cytotoxicity. Yoo, H.S., Norred, W.P., Showker, J., Riley, R.T. Toxicol. Appl. Pharmacol. (1996) [Pubmed]
  18. Inhibition of serine palmitoyltransferase in vitro and long-chain base biosynthesis in intact Chinese hamster ovary cells by beta-chloroalanine. Medlock, K.A., Merrill, A.H. Biochemistry (1988) [Pubmed]
  19. Serine-palmitoyl transferase activity in cultured human keratinocytes. Holleran, W.M., Williams, M.L., Gao, W.N., Elias, P.M. J. Lipid Res. (1990) [Pubmed]
  20. Hemoxidation and binding of the 46-kDa cystalysin of Treponema denticola leads to a cysteine-dependent hemolysis of human erythrocytes. Chu, L., Ebersole, J.L., Holt, S.C. Oral Microbiol. Immunol. (1999) [Pubmed]
  21. Chloralanyl and propargylglycyl dipeptides. Suicide substrate containing antibacterials. Cheung, K.S., Wasserman, S.A., Dudek, E., Lerner, S.A., Johnston, M. J. Med. Chem. (1983) [Pubmed]
  22. D-Cysteine desulfhydrase of Escherichia coli. Purification and characterization. Nagasawa, T., Ishii, T., Kumagai, H., Yamada, H. Eur. J. Biochem. (1985) [Pubmed]
  23. Inactivation of alanine racemase by beta-chloro-L-alanine released enzymatically from amino acid and peptide C10-esters of deacetylcephalothin. Mobashery, S., Johnston, M. Biochemistry (1987) [Pubmed]
  24. Chloroalanyl antibiotic peptides: antagonism of their antimicrobial effects by L-alanine and L-alanyl peptides in gram-negative bacteria. Cheung, K.S., Boisvert, W., Lerner, S.A., Johnston, M. J. Med. Chem. (1986) [Pubmed]
  25. Inhibition of cholesterol and sphingolipid synthesis causes paradoxical effects on permeability barrier homeostasis. Mao-Qiang, M., Feingold, K.R., Elias, P.M. J. Invest. Dermatol. (1993) [Pubmed]
  26. Tryptophan synthase mutations that alter cofactor chemistry lead to mechanism-based inactivation. Jhee, K.H., McPhie, P., Ro, H.S., Miles, E.W. Biochemistry (1998) [Pubmed]
  27. Physiological comparison of D-cysteine desulfhydrase of Escherichia coli with 3-chloro-D-alanine dehydrochlorinase of Pseudomonas putida CR 1-1. Nagasawa, T., Ishii, T., Yamada, H. Arch. Microbiol. (1988) [Pubmed]
  28. Evidence for two conformers of the beta subunit of tryptophan synthase in solution. Ahmed, S.A., Miles, E.W. J. Biol. Chem. (1992) [Pubmed]
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