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. 1967 Jul;104(1):205–211. doi: 10.1042/bj1040205

The phospholipids of Pneumococcus I-192R, A.T.C.C. 12213

Some structural rearrangements occurring under mild conditions

D E Brundish 1, N Shaw 1, J Baddiley 1
PMCID: PMC1270562  PMID: 4382428

Abstract

1. The phospholipids from the non-capsulated strain of Pneumococcus I–192R, A.T.C.C. 12213, were separated into three fractions by chromatography on columns of silicic acid and DEAE-cellulose (acetate form). 2. The water-soluble phosphate esters produced by deacylation of each fraction were separated by chromatography on columns of DEAE-cellulose (HCO3 form). 3. Three deacylated products, diglycerol phosphate, glycerylphosphorylglycerol phosphate and bis(glycerylphosphoryl)glycerol, were identified by analysis, by chemical degradations and by comparison with synthetic materials. 4. From a study of freshly isolated lipids prepared and worked up under conditions where exposure to acid was minimal, it was concluded that the Pneumococcus contains phosphatidylglycerol and bisphosphatidylglycerol, in the molar proportion 1:2·5–3·0, and that the deacylation product glycerylphosphorylglycerol phosphate was probably an artifact of the isolation procedure. 5. Acid-catalysed isomerization (phosphodiester migration) of diglycerol phosphate and bis(glycerylphosphoryl)glycerol and transesterification (glycerol phosphate transfer) of diglycerol phosphate were observed. The structures of the products were established by degradation. 6. A novel mechanism for the biosynthesis of bisphosphatidylglycerol is presented.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ANDERSON J. S., MATSUHASHI M., HASKIN M. A., STROMINGER J. L. LIPID-PHOSPHOACETYLMURAMYL-PENTAPEPTIDE AND LIPID-PHOSPHODISACCHARIDE-PENTAPEPTIDE: PRESUMED MEMBRANE TRANSPORT INTERMEDIATES IN CELL WALL SYNTHESIS. Proc Natl Acad Sci U S A. 1965 Apr;53:881–889. doi: 10.1073/pnas.53.4.881. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Brundish D. E., Shaw N., Baddiley J. The glycolipids from the non-capsulated strain of Pneumococcus I-192R, A.T.C.C. 12213. Biochem J. 1965 Oct;97(1):158–165. doi: 10.1042/bj0970158. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. COULON-MORELEC M. J., FAURE M., MARECHAL J. [Controlled degradation of diphosphatidylglycerol (cardiolipid) in an acid medium. Study of the phosphatide derivatives obtained]. Bull Soc Chim Biol (Paris) 1962;44:171–183. [PubMed] [Google Scholar]
  4. COULON-MORELEC M. J., FAURE M., MARECHAL J. [Study of the mechanism of the liberation of phosphatide diglycerides under the action of hot acetic acid]. Bull Soc Chim Biol (Paris) 1960;42:867–876. [PubMed] [Google Scholar]
  5. HANAHAN D. J., OLLEY J. N. Chemical nature of monophosphoinositides. J Biol Chem. 1958 Apr;231(2):813–828. [PubMed] [Google Scholar]
  6. HANES C. S., ISHERWOOD F. A. Separation of the phosphoric esters on the filter paper chromatogram. Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0. [DOI] [PubMed] [Google Scholar]
  7. KANFER J., KENNEDY E. P. METABOLISM AND FUNCTION OF BACTERIAL LIPIDS. II. BIOSYNTHESIS OF PHOSPHOLIPIDS IN ESCHERICHIA COLI. J Biol Chem. 1964 Jun;239:1720–1726. [PubMed] [Google Scholar]
  8. KATES M., YENGOYAN L. S., SASTRY P. S. A DIETHER ANALOG OF PHOSPHATIDYL GLYCEROPHOSPHATE IN HALOBACTERIUM CUTIRUBRUM. Biochim Biophys Acta. 1965 Apr 5;98:252–268. doi: 10.1016/0005-2760(65)90119-0. [DOI] [PubMed] [Google Scholar]
  9. LECOCQ J., BALLOU C. E. ON THE STRUCTURE OF CARDIOLIPIN. Biochemistry. 1964 Jul;3:976–980. doi: 10.1021/bi00895a023. [DOI] [PubMed] [Google Scholar]
  10. MACFARLANE M. G. Structure of cardiolipin. Nature. 1958 Oct 4;182(4640):946–946. doi: 10.1038/182946a0. [DOI] [PubMed] [Google Scholar]
  11. RAPPORT M. M., ALONZO N. Photometric determination of fatty acid ester groups in phospholipides. J Biol Chem. 1955 Nov;217(1):193–198. [PubMed] [Google Scholar]
  12. ROTHFIELD L., HORECKER B. L. THE ROLE OF CELL-WALL LIPID IN THE BIOSYNTHESIS OF BACTERIAL LIPOPOLYSACCHARIDE. Proc Natl Acad Sci U S A. 1964 Oct;52:939–946. doi: 10.1073/pnas.52.4.939. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Schwarz H. P., Dreisbach L., Polis E., Polis B. D., Soffer E. Effect of whole-body x-ray irradiation on phospholipids of rat liver particulate fractions. Arch Biochem Biophys. 1965 Aug;111(2):422–430. doi: 10.1016/0003-9861(65)90205-5. [DOI] [PubMed] [Google Scholar]
  14. Wells M. A., Dittmer J. C. The identification of glycerophosphorylglycerol phosphate as the deacylation product of a new brain lipid. J Biol Chem. 1966 May 10;241(9):2103–2105. [PubMed] [Google Scholar]

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