Methyl N-carbobenzoxy-β-iodo-D-alaninate (1) served as an intermediate to synthesize methyl β-iodo-D-alaninate (2) and β-iodo-D-alanine (3). The 125I-labeled compound 1 was synthesized by the melt method and used to synthesize 125I-labeled compounds 2 and 3. Compound 3 was shown to be substrate for D-amino acid oxidase. It was also shown that compounds 2 and 3 were rapidly eliminated from normal mammalian tissues and that compound 3 inhibited the Escherichia coli growth in a dose-dependent manner at 100–500 μg/ml while compound 2 showed no effect at 500 μg/ml level. Therefore, it was suggested that compound 3 may serve as an abscess localizing agent.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
Dang T-Y, Cheung Y-F, Walsh C (1976) Reactions of β-fluoroalanine and β-bromoalanine with D-amino acid oxidase. Biochem Biophys Res Comm 72:960–968
Davis BD, Mingioli ES (1950) Mutants of Escherichia coli requiring methionine or vitamin B12. Bacteriol 60:17–28
Kollonitsch J, Barash L, Kahan FM, Kropp H (1973) New antibacterial agent via photofluorination of a bacterial cell wall constituent. Nature 243: 346–347
Kollonitsch J, Barash L (1976) Organofluorine synthesis via photofluorination: 3-fluoro-D-alanine and 2-deuterio analogue, antibacterials related to the bacterial cell wall. J Am Chem Soc 98:5591–5593
Lee SW, Foley EJ, Epstein JA, Wallace JH (1944) Improvements in the turbidimetric assay for penicillin. J Biol Chem 152:485–486
Manning JM, Merrifield NE, Jones WM, Gotschlich EC (1974) Inhibition of bacterial growthy by β-chloro-D-alanine. Proc Nat Acad Sci USA 71:417–421
Shiue C-Y, Wolf AP (1980) Synthesis of 131I-labelled β-iodo-D-alanine and related compounds. J Lab Cmpd Radiopharm 17:53–58
Walsh C, Schonbrunn A, Abeles RH (1971) Studies on the mechanism of action of D-amino acid oxidase. J Biol Chem 246:6855–6866
Wood WA, Gunsalus IC (1951) D-Alanine formation: a racemase in Streptococcus faecalis. J Biol Chem 190:403–416
Research carried out at Brookhaven National Laboratory under contract with the U.S. Department of Energy (No. DE-AC-02-76CH00016) and supported by its Office of Health and Environmental Research
About this article
Cite this article
Shiue, C.-., Gallagher, B.M. & Wolf, A.P. 125I-β-iodo-D-alanine-synthesis, biodistribution and antimicrobial activity. Eur J Nucl Med 6, 245–248 (1981). https://doi.org/10.1007/BF00251346
- Public Health
- Escherichia Coli
- Nuclear Medicine
- Antimicrobial Activity