Abstract
Certain D-amino acids, such as D-methionine and D-cystine, were incorporated into cells of Escherichia coli under conditions inhibiting protein and cell wall synthesis. Part of the radioactivity of D-14C-amino acids incorporated into the cells was found in the isolated cell wall peptidoglycan. A covalent linkage between the amino group of the D-amino acids and the peptidoglycan was presumed to be the main cause of the binding of the D-amino acids to peptidoglycan, because the amino group of the D-amino acids in the incorporation product was substituted. Whether the carboxyl terminus was substituted was unknown. The formation of the D-amino acid-peptidoglycan linkage was insensitive to beta-lactam antibiotics such as benzylpenicillin and ampicillin (500 micrograms/ml) and therefore was not due to the reaction of DD-transpeptidation which is involved in the biosynthesis of peptidoglycan. The D-amino acids also strongly inhibited the formation of peptidoglycan-bound lipoprotein in the E. coli cells. The results may suggest the correlation between binding of D-amino acid to peptidoglycan and inhibition of formation of the bound form of lipoprotein.
Full text
PDF
Images in this article
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Braun V. Covalent lipoprotein from the outer membrane of Escherichia coli. Biochim Biophys Acta. 1975 Oct 31;415(3):335–377. doi: 10.1016/0304-4157(75)90013-1. [DOI] [PubMed] [Google Scholar]
- Hirashima A., Inouye M. Specific biosynthesis of an envelope protein of Escherichia coli. Nature. 1973 Apr 6;242(5397):405–407. doi: 10.1038/242405a0. [DOI] [PubMed] [Google Scholar]
- Hirota Y., Suzuki H., Nishimura Y., Yasuda S. On the process of cellular division in Escherichia coli: a mutant of E. coli lacking a murein-lipoprotein. Proc Natl Acad Sci U S A. 1977 Apr;74(4):1417–1420. doi: 10.1073/pnas.74.4.1417. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Inouye M., Guthrie J. P. A mutation which changes a membrane protein of E. coli. Proc Natl Acad Sci U S A. 1969 Nov;64(3):957–961. doi: 10.1073/pnas.64.3.957. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Inouye M., Shaw J., Shen C. The assembly of a structural lipoprotein in the envelope of Escherichia coli. J Biol Chem. 1972 Dec 25;247(24):8154–8159. [PubMed] [Google Scholar]
- Inukai M., Takeuchi M., Shimizu K., Arai M. Mechanism of action of globomycin. J Antibiot (Tokyo) 1978 Nov;31(11):1203–1205. doi: 10.7164/antibiotics.31.1203. [DOI] [PubMed] [Google Scholar]
- Iwamatsu K., Inouye S., Tsuruoka T., Mizutani K., Omoto S., Ogino H., Miyauchi K., Watanabe T., Niida T. Synthesis and biological activity of 7 beta-(2-amino-2-carboxy)-ethylthioacetamido-7 alpha-methoxycephalosporin derivatives. J Antibiot (Tokyo) 1983 Mar;36(3):229–241. doi: 10.7164/antibiotics.36.229. [DOI] [PubMed] [Google Scholar]
- Izaki K., Matsuhashi M., Strominger J. L. Glycopeptide transpeptidase and D-alanine carboxypeptidase: penicillin-sensitive enzymatic reactions. Proc Natl Acad Sci U S A. 1966 Mar;55(3):656–663. doi: 10.1073/pnas.55.3.656. [DOI] [PMC free article] [PubMed] [Google Scholar]
- LARK C., BRADLEY D., LARK K. G. FURTHER STUDIES ON THE INCORPORATION OF D-METHIONINE INTO THE BACTERIAL CELL WALL; ITS INCORPORATION INTO THE R-LAYER AND THE STRUCTURAL CONSEQUENCES. Biochim Biophys Acta. 1963 Oct 29;78:278–288. doi: 10.1016/0006-3002(63)91638-x. [DOI] [PubMed] [Google Scholar]
- LARK C., LARK K. G. The effects of D-amino acids on Alcaligenes fecalis. Can J Microbiol. 1959 Aug;5:369–379. doi: 10.1139/m59-046. [DOI] [PubMed] [Google Scholar]
- LENNOX E. S. Transduction of linked genetic characters of the host by bacteriophage P1. Virology. 1955 Jul;1(2):190–206. doi: 10.1016/0042-6822(55)90016-7. [DOI] [PubMed] [Google Scholar]
- Nakao H., Yanagisawa H., Shimizu B., Kaneko M., Nagano M. A new semisynthetic 7alpha-methoxycephalosporin, CS-1170: 7beta-((cyanomethyl)thio)acetamido)-7alpha-methoxy-3-((1-methyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid. J Antibiot (Tokyo) 1976 May;29(5):554–558. doi: 10.7164/antibiotics.29.554. [DOI] [PubMed] [Google Scholar]
- WEIDEL W., PELZER H. BAGSHAPED MACROMOLECULES--A NEW OUTLOOK ON BACTERIAL CELL WALLS. Adv Enzymol Relat Areas Mol Biol. 1964;26:193–232. doi: 10.1002/9780470122716.ch5. [DOI] [PubMed] [Google Scholar]