Abstract
When cultured in the presence of 600 mM D-mannitol, Escherichia coli K-12 cells synthesized two novel phospholipids. The identities of these compounds are postulated to be phosphatidylmannitol and diphosphatidylmannitol, the sugar alcohol analogs of phosphatidylglycerol and cardiolipin, respectively. The nonacylated glycerol moieties of the normal acidic phospholipids were substituted by D-mannitol. The formation of the analogs was significantly enhanced when strains harboring the pss-1 allele, a temperature-sensitive mutation in phosphatidylserine synthase (Ohta and Shibuya, J. Bacteriol. 132:434-443, 1977), were grown at 42 degrees C, and the accumulation of the analogs was maximum in late stationary phase; more than 90% of the total cellular lipids were these novel phospholipids. Strains with a defective cardiolipin synthase (Pluschke et al., J. Biol. Chem. 253:5048-5055, 1978) failed to form the analog lipids, whereas cells with increased cardiolipin synthase activity due to the presence of a pBR322-derived recombinant plasmid containing the structural gene for cardiolipin synthase produced more mannitol lipids than wild-type strains. These observations and the structures of the analog lipids indicated that cardiolipin synthase participates in the formation of these novel phospholipids. We suggest that reversible alcoholysis and condensation, in addition to low substrate specificity of the enzyme, are the mechanisms involved in this process. Addition to the medium of other straight-chain alditols, D-arabitol, ribitol, xylitol, erythritol, and L-threitol also yielded pairs of novel phospholipids, whereas sorbitol or galactitol produced only one analog in small quantities. These acidic phospholipid analogs have not been reported in any living system. They should be useful in the study of structure-function relationships of phospholipids and in manipulating the structures of various membrane systems.
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.
- Ames G. F. Lipids of Salmonella typhimurium and Escherichia coli: structure and metabolism. J Bacteriol. 1968 Mar;95(3):833–843. doi: 10.1128/jb.95.3.833-843.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
- BENSON A. A., MARUO B. Piant phospholipids. I. Identification of the phosphatidyl glycerols. Biochim Biophys Acta. 1958 Jan;27(1):189–195. doi: 10.1016/0006-3002(58)90308-1. [DOI] [PubMed] [Google Scholar]
- Bachmann B. J. Pedigrees of some mutant strains of Escherichia coli K-12. Bacteriol Rev. 1972 Dec;36(4):525–557. doi: 10.1128/br.36.4.525-557.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Bell R. M. Mutants of Escherichia coli defective in membrane phospholipid synthesis: macromolecular synthesis in an sn-glycerol 3-phosphate acyltransferase Km mutant. J Bacteriol. 1974 Mar;117(3):1065–1076. doi: 10.1128/jb.117.3.1065-1076.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cronan J. E., Jr, Gelmann E. P. Physical properties of membrane lipids: biological relevance and regulation. Bacteriol Rev. 1975 Sep;39(3):232–256. doi: 10.1128/br.39.3.232-256.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Griggs L. J., Post A., White E. R., Finkelstein J. A., Moeckel W. E., Holden K. G., Zarembo J. E., Weisbach J. A. Identification and quantitation of alditol acetates of neutral and amino sugars from mucins by automated gas-liquid chromatography. Anal Biochem. 1971 Oct;43(2):369–381. doi: 10.1016/0003-2697(71)90266-1. [DOI] [PubMed] [Google Scholar]
- Hirschberg C. B., Kennedy E. P. Mechanism of the enzymatic synthesis of cardiolipin in Escherichia coli. Proc Natl Acad Sci U S A. 1972 Mar;69(3):648–651. doi: 10.1073/pnas.69.3.648. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Kito M., Aibara S., Kato M., Hata T. Differences in fatty acid composition among phosphatidylethanolamine, phosphatidylglycerol and cardiolipin of Escherichia coli. Biochim Biophys Acta. 1972 Mar 23;260(3):475–478. doi: 10.1016/0005-2760(72)90062-8. [DOI] [PubMed] [Google Scholar]
- Lee C. A., Jacobson G. R., Saier M. H., Jr Plasmid-directed synthesis of enzymes required for D-mannitol transport and utilization in Escherichia coli. Proc Natl Acad Sci U S A. 1981 Dec;78(12):7336–7340. doi: 10.1073/pnas.78.12.7336. [DOI] [PMC free article] [PubMed] [Google Scholar]
- McIntyre T. M., Chamberlain B. K., Webster R. E., Bell R. M. Mutants of Escherichia coli defective in membrane phospholipid synthesis. Effects of cessation and reinitiation of phospholipid synthesis on macromolecular synthesis and phospholipid turnover. J Biol Chem. 1977 Jul 10;252(13):4487–4493. [PubMed] [Google Scholar]
- Ohta A., Shibuya I. Membrane phospholipid synthesis and phenotypic correlation of an Escherichia coli pss mutant. J Bacteriol. 1977 Nov;132(2):434–443. doi: 10.1128/jb.132.2.434-443.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pluschke G., Hirota Y., Overath P. Function of phospholipids in Escherichia coli. Characterization of a mutant deficient in cardiolipin synthesis. J Biol Chem. 1978 Jul 25;253(14):5048–5055. [PubMed] [Google Scholar]
- Raetz C. R. Enzymology, genetics, and regulation of membrane phospholipid synthesis in Escherichia coli. Microbiol Rev. 1978 Sep;42(3):614–659. doi: 10.1128/mr.42.3.614-659.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Raetz C. R., Kantor G. D., Nishijima M., Newman K. F. Cardiolipin accumulation in the inner and outer membranes of Escherichia coli mutants defective in phosphatidylserine synthetase. J Bacteriol. 1979 Aug;139(2):544–551. doi: 10.1128/jb.139.2.544-551.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Solomon E., Lin E. C. Mutations affecting the dissimilation of mannitol by Escherichia coli K-12. J Bacteriol. 1972 Aug;111(2):566–574. doi: 10.1128/jb.111.2.566-574.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]