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. 1968 Jun;108(2):211–219. doi: 10.1042/bj1080211

The chemical synthesis of glucosaminylphosphatidylglycerol. Comparison with a new phospholipid isolated from Bacillus megaterium

M I Gurr 1,*, P P M Bonsen 1, J A F OP Den Kamp 1, L L M Van Deenen 1
PMCID: PMC1198795  PMID: 4969864

Abstract

1. We describe the synthesis of a glucosamine derivative of phosphatidylglycerol having the same structure as that of the natural compound isolated from Bacillus megaterium. 2. 2-O-(3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-d-glucopyranosyl)-3-O-benzyl-1-iodo-sn-glycerol was prepared by a Königs–Knorr condensation between 3-O-benzyl-1-toluene-p-sulphonyl-sn-glycerol and 3,4,6-tri-O-acetyl-1-bromo-2-deoxy-2-phthalimido-d-glucopyranose followed by replacement of the toluene-p-sulphonyl group with iodine. The iodide was treated with the silver salt of 2-isolauroyl-1-oleoyl-sn-glycerol 3-(monobenzyl hydrogen phosphate) to form the fully protected phosphoglycolipid. 3. Removal of benzyl protecting groups by catalytic hydrogenolysis, phthaloyl group with hydrazine and acetyl groups with pH10 buffer furnished 2-O-(2-amino-2-deoxy-d-glucopyranosyl)-1-(2-isolauroyl-1-stearoyl-sn-glycero-3-phosphoryl)-sn-glycerol. 4. The synthetic and natural compounds appeared identical when compared by chromatography and by identification of hydrolysis products from chemical and enzymic degradations.

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Selected References

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  1. BADDILEY J., BUCHANAN J. G., RAJBHANDARY U. L., SANDERSON A. R. Teichoic acid from the walls of Staphylococcus aureus H. Structure of the N-acetylglucosaminyl-ribitol residues. Biochem J. 1962 Mar;82:439–448. doi: 10.1042/bj0820439. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BALLOU C. E. Alkali-sensitive glycosides. Adv Carbohydr Chem. 1954;9:59–95. doi: 10.1016/s0096-5332(08)60372-0. [DOI] [PubMed] [Google Scholar]
  3. Baer E., Rao K. V. Lipoamino acid. Synthesis of amino acid esters of phosphatidyl glycerols. Can J Biochem. 1966 Jun;44(6):899–915. doi: 10.1139/o66-107. [DOI] [PubMed] [Google Scholar]
  4. Bonsen P. P., de Haas G. H., van Deenen L. L. Synthesis and enzymic hydrolysis of an O-alanyl ester of phosphatidyl glycerol. Biochim Biophys Acta. 1965 Jul 7;106(1):93–105. doi: 10.1016/0005-2760(65)90098-6. [DOI] [PubMed] [Google Scholar]
  5. Bonsen P. P., de Haas G. H., van Deenen L. L. Synthetic and structural investigations on 3-phosphatidyl-1'-(3'-O-L-lysyl)glycerol. Biochemistry. 1967 Apr;6(4):1114–1120. doi: 10.1021/bi00856a021. [DOI] [PubMed] [Google Scholar]
  6. DAWSON R. M. A hydrolytic procedure for the identification and estimation of individual phospholipids in biological samples. Biochem J. 1960 Apr;75:45–53. doi: 10.1042/bj0750045. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. GALE E. F., FOLKES J. P. THE INCORPORATION OF GLYCEROL AND LYSINE INTO THE LIPID FRACTION OF STAPHYLOCOCCUS AUREUS. Biochem J. 1965 Feb;94:390–400. doi: 10.1042/bj0940390. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. HOUTSMULLER U. M., van DEENEN L. Identification of a bacterial phospholipid as an O-ornithine ester of phosphatidyl glycerol. Biochim Biophys Acta. 1963 Apr 23;70:211–213. doi: 10.1016/0006-3002(63)90743-1. [DOI] [PubMed] [Google Scholar]
  9. Houtsmuller U. M., van Deenen L. L. On the amino acid esters of phosphatidyl glycerol from bacteria. Biochim Biophys Acta. 1965 Dec 2;106(3):564–576. doi: 10.1016/0005-2760(65)90072-x. [DOI] [PubMed] [Google Scholar]
  10. Lennarz W. J., Bonsen P. P., van Deenen L. L. Substrate specificity of O-L-lysylphosphatidylglycerol synthetase. Enzymatic studies on the structure of O-L-lysylphosphatidylglycerol. Biochemistry. 1967 Aug;6(8):2307–2312. doi: 10.1021/bi00860a005. [DOI] [PubMed] [Google Scholar]
  11. Lennarz W. J., Nesbitt J. A., 3rd, Reiss J. The participation of sRNA in the enzymatic synthesis of O-L-lysyl phosphatidylgylcerol in Staphylococcus aureus. Proc Natl Acad Sci U S A. 1966 Apr;55(4):934–941. doi: 10.1073/pnas.55.4.934. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. TREVELYAN W. E., PROCTER D. P., HARRISON J. S. Detection of sugars on paper chromatograms. Nature. 1950 Sep 9;166(4219):444–445. doi: 10.1038/166444b0. [DOI] [PubMed] [Google Scholar]
  13. den Kamp JA O. P., Houtsmuller U. M., van Deenen L. L. On the phospholipids of Bacillus megaterium. Biochim Biophys Acta. 1965 Oct 4;106(2):438–441. doi: 10.1016/0005-2760(65)90059-7. [DOI] [PubMed] [Google Scholar]

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