β-Chloro-D-alanine
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β-Chloro-D-alanine is a compound that functions as an inhibitor of enzymes involved in the biosynthesis of peptidoglycan, a crucial component of bacterial cell walls. It exerts its mode of action by irreversibly binding to the active site of alanine racemase, an enzyme responsible for converting L-alanine to D-alanine, an essential building block for peptidoglycan synthesis. β-Chloro-D-alanine disrupts the production of D-alanine, leading to the impairment of peptidoglycan formation and ultimately causing bacterial cell lysis. β-Chloro-D-alanine involves the formation of a covalent bond with the active site cysteine residue of alanine racemase, thereby preventing the enzyme from carrying out its catalytic function. β-Chloro-D-alanine demonstrates potential as a tool for studying bacterial cell wall biosynthesis and as a chemical probe for investigating the role of peptidoglycan in bacterial physiology.
β-Chloro-D-alanine References
- The effect of beta-chloro D-alanine and L-cycloserine on the serine, phosphorus and palmitic acid uptake and metabolism of Tetrahymena lipids. | Kovács, P. 1999. Acta Biol Hung. 50: 363-73. PMID: 10735173
- Synergic activity of D-cycloserine and beta-chloro-D-alanine against Mycobacterium tuberculosis. | David, S. 2001. J Antimicrob Chemother. 47: 203-6. PMID: 11157908
- Structural requirements for activation of the glycine coagonist site of N-methyl-D-aspartate receptors expressed in Xenopus oocytes. | McBain, CJ., et al. 1989. Mol Pharmacol. 36: 556-65. PMID: 2554111
- Glutamate Racemase Is the Primary Target of β-Chloro-d-Alanine in Mycobacterium tuberculosis. | Prosser, GA., et al. 2016. Antimicrob Agents Chemother. 60: 6091-9. PMID: 27480853
- yggS Encoding Pyridoxal 5'-Phosphate Binding Protein Is Required for Acidovorax citrulli Virulence. | Wang, Y., et al. 2021. Front Microbiol. 12: 783862. PMID: 35087487
- Development of a Chemogenetic Approach to Manipulate Intracellular pH. | Ghaffari Zaki, A., et al. 2023. J Am Chem Soc. 145: 11899-11902. PMID: 37222194
- Inhibition of bacterial growth by beta-chloro-D-alanine. | Manning, JM., et al. 1974. Proc Natl Acad Sci U S A. 71: 417-21. PMID: 4150023
- D-Amino acid dehydrogenase of Escherichia coli K12: positive selection of mutants defective in enzyme activity and localization of the structural gene. | Wild, J. and Klopotowski, T. 1981. Mol Gen Genet. 181: 373-8. PMID: 6113535
- Antibiotic-tolerant mutants of Streptococcus pneumoniae that are not deficient in autolytic activity. | Williamson, R. and Tomasz, A. 1980. J Bacteriol. 144: 105-13. PMID: 6903187
- Synergy in the antimicrobial action of penicillin and beta-chloro-D-alanine in vitro. | Soper, TS. and Manning, JM. 1976. Antimicrob Agents Chemother. 9: 347-9. PMID: 773296
- Catalytic ability and stability of two recombinant mutants of D-amino acid transaminase involved in coenzyme binding. | Van Ophem, PW., et al. 1995. Protein Sci. 4: 2578-86. PMID: 8580849
- Inactivation of bacterial D-amino acid transaminase by beta-chloro-D-alanine. | Soper, TS., et al. 1977. J Biol Chem. 252: 3170-5. PMID: 863877
- Suppression of beta-lactam antibiotic resistance in a methicillin-resistant Staphylococcus aureus through synergic action of early cell wall inhibitors and some other antibiotics. | Sieradzki, K. and Tomasz, A. 1997. J Antimicrob Chemother. 39 Suppl A: 47-51. PMID: 9511062
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
β-Chloro-D-alanine, 1 g | sc-476009 | 1 g | $188.00 | |||
β-Chloro-D-alanine, 5 g | sc-476009A | 5 g | $676.00 |