Abstract
Lipoteichoic acid (LTA) from Lactobacillus casei contains poly(glycerophosphate) substituted with D-alanyl ester residues. The distribution of these residues in the in vitro-synthesized polymer is uniform. Esterification of LTA with D-alanine may occur in one of two modes: (i) addition at random or (ii) addition at a defined locus in the poly(glycerophosphate) chain followed by redistribution of the ester residues. A time-dependent transacylation of these residues from D-[14C]alanyl-lipophilic LTA to hydrophilic acceptor was observed. The hydrophilic acceptor was characterized as D-alanyl-hydrophilic LTA. This transacylation requires neither ATP nor the D-alanine incorporation system, i.e., the D-alanine activating enzyme and D-alanine:membrane acceptor ligase. No evidence for an enzyme-catalyzed transacylation reaction was observed. We propose that this process of transacylation may be responsible for the redistribution of D-alanyl residues after esterification to the poly(glycerophosphate). As a result, it is difficult to distinguish between these proposed modes of addition.
Full text
PDF![1191](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85bf/215903/7a8e08b8ad72/jbacter00223-0343.png)
![1192](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85bf/215903/6d731e039c7f/jbacter00223-0344.png)
![1193](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85bf/215903/179a47a85806/jbacter00223-0345.png)
![1194](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85bf/215903/96c90d641ff6/jbacter00223-0346.png)
![1195](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85bf/215903/2c3bde07f1e9/jbacter00223-0347.png)
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- BLIGH E. G., DYER W. J. A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959 Aug;37(8):911–917. doi: 10.1139/o59-099. [DOI] [PubMed] [Google Scholar]
- Brautigan V. M., Childs W. C., 3rd, Neuhaus F. C. Biosynthesis of D-alanyl-lipoteichoic acid in Lactobacillus casei: D-alanyl-lipophilic compounds as intermediates. J Bacteriol. 1981 Apr;146(1):239–250. doi: 10.1128/jb.146.1.239-250.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cabacungan E., Pieringer R. A. Mode of elongation of the glycerol phosphate polymer of membrane lipoteichoic acid of Streptococcus faecium ATCC 9790. J Bacteriol. 1981 Jul;147(1):75–79. doi: 10.1128/jb.147.1.75-79.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Childs W. C., 3rd, Neuhaus F. C. Biosynthesis of D-alanyl-lipoteichoic acid: characterization of ester-linked D-alanine in the in vitro-synthesized product. J Bacteriol. 1980 Jul;143(1):293–301. doi: 10.1128/jb.143.1.293-301.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fischer W. D-alanine ester-containing glycerophosphoglycolipids in the membrane of gram-positive bacteria. Biochim Biophys Acta. 1982 May 13;711(2):372–375. doi: 10.1016/0005-2760(82)90048-0. [DOI] [PubMed] [Google Scholar]
- Fischer W., Koch H. U., Rösel P., Fiedler F. Alanine ester-containing native lipoteichoic acids do not act as lipoteichoic acid carrier. Isolation, structural and functional characterization. J Biol Chem. 1980 May 25;255(10):4557–4562. [PubMed] [Google Scholar]
- Fischer W., Laine R. A., Nakano M. On the relationship between glycerophosphoglycolipids and lipoteichoic acids in Gram-positive bacteria. II. Structures of glycerophosphoglycolipids. Biochim Biophys Acta. 1978 Mar 30;528(3):298–308. doi: 10.1016/0005-2760(78)90019-x. [DOI] [PubMed] [Google Scholar]
- Fischer W., Nakano M., Laine R. A., Bohrer W. On the relationship between glycerophosphoglycolipids and lipoteichoic acids in Gram-positive bacteria. I. The occurrence of phosphoglycolipids. Biochim Biophys Acta. 1978 Mar 30;528(3):288–297. doi: 10.1016/0005-2760(78)90018-8. [DOI] [PubMed] [Google Scholar]
- Fischer W., Rösel P., Koch H. U. Effect of alanine ester substitution and other structural features of lipoteichoic acids on their inhibitory activity against autolysins of Staphylococcus aureus. J Bacteriol. 1981 May;146(2):467–475. doi: 10.1128/jb.146.2.467-475.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
- LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
- Laine R. A., Fischer W. On the relationship between glycerophosphoglycolipids and lipoteichoic acids of gram-positive bacteria. III. Di(glycerophospho)-acylkojibiosyldiacylglycerol and related compounds from Streptococcus lactis NCDO 712. Biochim Biophys Acta. 1978 May 25;529(2):250–262. doi: 10.1016/0005-2760(78)90068-1. [DOI] [PubMed] [Google Scholar]
- Lambert P. A., Hancock I. C., Baddiley J. Influence of alanyl ester residues on the binding of magnesium ions to teichoic acids. Biochem J. 1975 Dec;151(3):671–676. doi: 10.1042/bj1510671. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Lambert P. A., Hancock I. C., Baddiley J. Occurrence and function of membrane teichoic acids. Biochim Biophys Acta. 1977 May 31;472(1):1–12. doi: 10.1016/0304-4157(77)90012-0. [DOI] [PubMed] [Google Scholar]
- Linzer R., Neuhaus F. C. Biosynthesis of membrane teichoic acid. A role of the D-alanine-activating enzyme. J Biol Chem. 1973 May 10;248(9):3196–3201. [PubMed] [Google Scholar]
- Loftfield R. B. The mechanism of aminoacylation of transfer RNA. Prog Nucleic Acid Res Mol Biol. 1972;12:87–128. doi: 10.1016/s0079-6603(08)60660-1. [DOI] [PubMed] [Google Scholar]
- Naumova I. B. Teikhoevye Kisloty v peguliatsii Viokhimicheskikh Protsessov u mikroorganizmov. Biokhimiia. 1978 Feb;43(2):195–207. [PubMed] [Google Scholar]
- Neuhaus F. C., Linzer R., Reusch V. M., Jr Biosynthesis of membrane teichoic acid: role of the D-alanine-activating enzyme and D-alanine: membrane acceptor ligase. Ann N Y Acad Sci. 1974 May 10;235(0):502–518. doi: 10.1111/j.1749-6632.1974.tb43287.x. [DOI] [PubMed] [Google Scholar]
- PATTERSON M. S., GREENE R. C. MEASUREMENT OF LOW ENERGY BETA-EMITTERS IN AQUEOUS SOLUTION BY LIQUID SCINTILLATION COUNTING OF EMULSIONS. Anal Chem. 1965 Jun;37:854–857. doi: 10.1021/ac60226a017. [DOI] [PubMed] [Google Scholar]
- Reusch V. M., Jr, Neuhaus F. C. D-Alanine: membrane acceptor ligase from Lactobacillus casei. J Biol Chem. 1971 Oct 25;246(20):6136–6143. [PubMed] [Google Scholar]
- SHABAROVA Z. A., HUGHES N. A., BADDILEY J. The influence of adjacent phosphate and hydroxyl groups on amino acid esters. Biochem J. 1962 Apr;83:216–219. doi: 10.1042/bj0830216. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Schneider J. E., Kennedy E. P. A novel phosphodiesterase from Aspergillus niger and its application to the study of membrane-derived oligosaccharides and other glycerol-containing biopolymers. J Biol Chem. 1978 Nov 10;253(21):7738–7743. [PubMed] [Google Scholar]
- Taron D. J., Childs W. C., 3rd, Neuhaus F. C. Biosynthesis of D-alanyl-lipoteichoic acid: role of diglyceride kinase in the synthesis of phosphatidylglycerol for chain elongation. J Bacteriol. 1983 Jun;154(3):1110–1116. doi: 10.1128/jb.154.3.1110-1116.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]