The reaction of phosphoglycolipids and other lipids with hydrofluoric acid

Shaw, N.; Stead, A.H.

doi:10.1042/bj1430461

Cited by 22 publications

(10 citation statements)

References 20 publications

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“…Each of these fragments contained glycerol and fatty acids in a molar ratio of 1:2. The 1,3-diacylglycerol as well as two minor fragments, mono-and triacylglycerol, most likely arose from 1,2-diacylglycerol by transesterification during the HF treatment (25). The acylglycerol derivatives obtained from the diacyl LTAs of the remaining group B strains were the same as those from the diacyl LTA of B. coagulans AHU 1634.…”

Section: Methodsmentioning

confidence: 81%

Comparative studies of lipoteichoic acids from several Bacillus strains

Iwasaki¹,

Shimada²,

Ito³

1986

J Bacteriol

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Structural studies were carried out on lipoteichoic acids obtained from defatted cells of 10 Bacillus strains by phenol-water partition followed by chromatography on DEAE-Sephacel and Octyl-Sepharose columns. A group of the tested bacteria (group A), BaciUus subtilis, Bacillus licheniformis, and Bacillus pumilus, was shown to have a diacyl form of lipoteichoic acids which contained D-alanine, D-glucose, D-glucosamine, fatty acids, and glycerol in molar ratios to phosphorus of 0.35 to 0.69, 0.07 to 0.15, 0.15 to 0.43, 0.06 to 0.11, and 0.95 to 1.18, respectively, whereas the other group (group B), Bacillus coagulans and Bacillus megaterium, had diacyl lipoteichoic acids which contained D-galactose, fatty acids, and glycerol in molar ratios to phosphorus of 0.05 to 0.42, 0.06 to 0.12, and 0.96 to 1.07, respectively. After treatment with 47% hydrogen fluoride, the lipoteichoic acids obtained from group A strains commonly gave a hydrophobic fragment, gentiobiosyl-P(1-*1 or 3)diacylglycerol, in addition to dephosphorylated repeating units, glycerol, 2-D-alanylglycerol, N-acetyl-Dglucosaminyl-a(1-+2)glycerol, and D-alanyl-N-acetyl-D-glucosaminyl-oa(1--*2)glycerol, whereas the lipoteichoic acids from group B strains yielded diacylglycerol in addition to glycerol and D-galactosyl-a(1--2)glycerol. The results together with data from Smith degradations indicate that in the lipoteichoic acids of group A strains the polymer chains, made up of partially alanylated glycerol phosphate and glycosylglycerol phosphate units, are joined to the acylglycerol anchors through gentiobiose. However, in the lipoteichoic acids of group B strains, the partially galactosylated poly(glycerol phosphate) chains are believed to be directly linked to the acylglycerol anchors.

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Section: Methodsmentioning

confidence: 81%

Comparative studies of lipoteichoic acids from several Bacillus strains

Iwasaki¹,

Shimada²,

Ito³

1986

J Bacteriol

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“…Since the phosphodiester group in phospholipids is susceptible to the action of H F (Shaw & Stead, 1974) and yeast walls may contain small amounts of phospholipid, the effect of lipid extraction on the rates of floc sedimentation was examined. Lipid-depleted organisms of strains ~c u c 3 6 6 and N C Y C I O O~ formed flocs and sedimented at the same rate as untreated organisms, but the rate at which organisms of the more flocculent strains sedimented after lipid extraction was appreciably reduced ( Table 2 ) .…”

Section: # ------7 R----------h___--\ 7 -R-----h----mentioning

confidence: 99%

“…A technique was used which excises from the wall mannan phosphodiester linkages and mannose residues distal to the phosphodiester linkages. The technique, in which organisms and walls are treated with hydrofluoric acid (HF), has previously been used to excise phosphodiester linkages from other polymers including teichoic acids (Glaser & Burger, 1964 ;Archibald, Baddiley & Shaukat, 1968) and bacterial phospholipids (Shaw & Stead, 1974), as well as from mannan extracted from S. cerevisiae (Cawley, Harrington & Letters, 1972). The reaction catalysed by HF may be represented as :…”

Section: Introductionmentioning

confidence: 99%

Role of Wall Phosphomannan in Flocculation of Saccharomyces cerevisiae

Jayatissa

Rose

1976

Journal of General Microbiology

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S U M M A R YTreatment with 60 yo hydrofluoric acid (HF) removed most of the phosphorus and small amounts of mannan, glucan and protein from walls of two nonflocculent strains ( N C Y C~~~ and NCYCI004) and two flocculent strains (NCYCIOOS and NCYC I 063) of Saccharornyces cerevisiae. Organisms of all strains showed increased flocculating ability following H F treatment. Flocculation of untreated organisms of NCYCIOOS and N C Y C I O~~, and of HF-treated organisms of all four strains, declined appreciably when they were washed in deionized water, with or without EDTA, and the flocculation was measured in deionized water instead of in 0.05 M-sodium acetate containing Ca2 +. Treatment with I ,a-epoxypropane also caused a decrease in the flocculating ability of these organisms. Extracting the lipids from organisms of strains N C Y C~~~ and N C Y C I O O~ had no effect on their flocculating ability, but decreased the flocculating ability of organisms of strains NCYCIOO5 and N C Y C I O~~. pH-electrophoretic mobility curves of untreated and HF-treated organisms confirmed the loss of wall phosphate by H F treatment, and indicated that HF treatment had little effect on the content of protein carboxyl groups in the outer wall layers. Mannose at 0 . 2 2~ completely prevented floc formation by organisms of strain N C Y C I O~~ ; but, even at 0.33 M, it had very little effect on floc formation by HF-treated organisms of strains ~c u c 3 6 6 and ~c u c r o 6 3 . Organisms of all four strains bound fluorescein-conjugated concanavalin A to the same extent after treatment with HF as before, but this treatment led to a greatly diminished binding of fluorescein-conjugated antiserum raised against organisms of strain N C Y C~~~. The results indicate that phosphodiester linkages in yeast-wall mannan are not involved in bridge formation through Ca2 + during floc formation and that this arises principally through carboxyl groups.

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“…leased almost quantitatively the PPG glycans from the protein backbone (see above). Since these hydrolysis conditions do not cleave glycosidic bonds (5,6,29,42,44), it is likely that all the glycans were linked to the protein by mild acid-and HF-labile phosphodiesters similar to the main glycans in L. mexicana sAP (18) and not by N-or O-glycosidic linkages. Phosphoamino acid analysis of the PPG protein backbone indicated the presence of large amounts of Ser(P) (Fig.…”

Section: Fig 4 High Ph Anion Exchange Hplc Profiles Of L Major Ppgmentioning

confidence: 99%

Purification and Structural Characterization of a Filamentous, Mucin-like Proteophosphoglycan Secreted by Leishmania Parasites

Ilg

Stierhof

Craik

et al. 1996

Journal of Biological Chemistry

108

137

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Parasitic protozoa of the genus Leishmania secrete a filamentous macromolecule that forms networks and appears to be associated with cell aggregation. We report here the purification of this parasite antigen from Leishmania major culture supernatant and its compositional (75.6% carbohydrate, 20% phosphate, 4.4% amino acids, w/w), structural, and ultrastructural characterization as a highly unusual proteophosphoglycan (PPG). Mild acid hydrolysis, which cleaves preferentially hexose 1-phosphate bonds, releases the PPG glycans. Their structures are Gal␤1-4Man, Man␣1-2Man, Gal␤1-3Gal␤1-4Man, PO 4 -6(Gal␤1-3) 0 -2 Gal␤1-4Man, and PO 4 -6(Ara␤1-2Gal␤1-3)Gal␤1-4Man. These glycans are also components of the parasite glycolipid lipophosphoglycan, but their relative abundance and structural organization in PPG are different. Some of them represent novel forms of protein glycosylation. 31 P NMR on native PPG demonstrates that phosphate is exclusively in phosphodiester bonds and that the basic structure R-Man␣1-PO 4 -6-Gal-R connects the glycans. A phosphodiester linkage to phosphoserine (most likely R-Man␣1-PO 4 -Ser) anchors the PPG oligosaccharides to the polypeptide. PPG has a unique amino acid composition; glycosylated phosphoserine (>43 mol %), serine, alanine, and proline account for more than 87 mol % and appear to be clustered in large proteinase-resistant domains. Electron microscopy of purified PPG reveals cable-like, flexible, long (to 6 m), and unbranched filaments. The overall structure of PPG shows many similarities to mammalian mucins. Potential functions of this novel mucin-like molecule for the parasites are discussed.Parasitic protozoa of the genus Leishmania are the causative agent of a wide range of human and animal diseases, which are transmitted by an insect vector, the sandfly. The digenetic life cycle of the parasite encompasses the infective metacyclic and several forms of procyclic, extracellular promastigotes in the digestive tract of the insect and the intracellular amastigotes residing in parasitophorous vacuoles of the mammalian host cells, the macrophages. Expression of complex and unique glycoconjugates appears to be crucial for the survival and development of the parasites in the sandfly vector and the mammalian host (reviewed in Refs. 1-3). The dominant cell surface glycolipid of Leishmania promastigotes is lipophosphoglycan (LPG). 1 In the sandfly, LPG serves as a ligand for the attachment of procyclic promastigotes to the midgut wall lining and may protect the parasites against the hydrolytic environment of the insect's digestive tract. After transmission of metacyclic promastigotes to the mammalian host, LPG confers complement resistance; it has been shown to act as a receptor for invasion of macrophages and may protect the parasites against the microbicidal response of the host cell (reviewed in Refs. 1, 2).The structure of LPG from five different Leishmania species has been described (4 -10), including life stage-and strainspecific features (8,11,12). Conserved structural elements are...

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The reaction of phosphoglycolipids and other lipids with hydrofluoric acid

Cited by 22 publications

References 20 publications

Comparative studies of lipoteichoic acids from several Bacillus strains

Comparative studies of lipoteichoic acids from several Bacillus strains

Role of Wall Phosphomannan in Flocculation of Saccharomyces cerevisiae

Purification and Structural Characterization of a Filamentous, Mucin-like Proteophosphoglycan Secreted by Leishmania Parasites

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