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Chemical Compound Review

Mannolipid     [ (6E,10E,14E,18E,22E,26E,30E,34 E,38E,42E...

Synonyms: AC1O5I44, 55598-56-6, Dolichyl mannosyl phosphate, DOLICHOL MONOPHOSPHATE MANNOSE
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Disease relevance of Dolichyl mannosyl phosphate


High impact information on Dolichyl mannosyl phosphate

  • This is followed by fatty acylation of the inositol ring, sequential addition of mannose residues donated by dolichyl mannosyl phosphate, and finally addition of ethanolamine phosphate [3].
  • The endogenous mannolipid was sensitive to mild base hydrolysis and mannose was released from the mannolipid by snake venom phosphodiesterase digestion [4].
  • A double-labeled mannolipid was synthesized in incubations containing hamster liver membranes, GDP-[14C]mannose, and [3H]phosphatidic acid [4].
  • Glucosyl-phosphoryldolichol, di-N-acetylchitobiosyl-pyrophosphoryl-dolichol and also GDP-mannose are still present, indicating that the formation of mannosyl-phosphoryl-dolichol and hence glycosylation of proteins via the lipid-linked oligosaccharide (Glc)3(Man)9(GlcNAc)2-pyrophosphoryl-dolichol, are under metabolic control [5].
  • The glycosyl donor function of the polyisoprenyl mannosyl phosphate in the second reaction of the mannosylation sequence could be directly demonstrated by the transfer of [14C]mannose from purified endogenous mannolipid to either methyl-alpha-D-mannoside or dinitrophenyl unit A glycopeptides by thyroid enzyme in the presence of Triton X-100 [6].

Biological context of Dolichyl mannosyl phosphate

  • Despite the absence of mannosyl-phosphoryl-dolichol protein glycosylation is not blocked [5].
  • When measured as a function of substrate concentration, the synthesis of the mannolipid was a nearly linear function of GDP-Man concentration in the range of 5 to 32 microM whereas protein mannosylation exhibited hyperbolic kinetics with saturation reached at about 10 microM [7].
  • The increased mannosyl transferase-dependent mannolipid formation in adult females may reflect a higher energy demand by these parasites, which is probably associated with oogenesis [8].
  • Antiserum against Man beta 1-4Glc beta 1-1Ceramide (MIOse2Cer), a mannolipid isolated from spermatozoa of the fresh-water bivalve, Hyriopsis schlegellii, has been elicited in rabbits by repeated injection of a mixture of hapten-bovine serum albumin (1:1, mg/ml) with Freund's adjuvant [9].

Anatomical context of Dolichyl mannosyl phosphate


Associations of Dolichyl mannosyl phosphate with other chemical compounds


Gene context of Dolichyl mannosyl phosphate

  • The chain length of the dolichyl moiety also influenced the mannolipid-enzyme interaction as the partially purified PMT1 had a higher affinity for Man-P-Dol95 than for Man-P-Dol55 [18].
  • To define the structural specificity of the mannolipid-mediated activation of GPT1, the ability of a variety of mannosylphosphorylisoprenols to stimulate GlcNAc-lipid biosynthesis in microsomal preparations from retinas of the embryonic chick has been tested [19].
  • Stimulation of mannolipid synthesis showed a correlation with the 11 beta, 17 alpha, 21-trihydroxy structure of C21 steroids [11].
  • The initial rate of synthesis of dolichyl mannosyl phosphate from GDP-D-[14C]mannose and exogenous dolichyl phosphate was highest in an intermediate cell fraction having a low specific activity of sucrase and alkaline phosphatase and an intermediate specific activity of thymidine kinase [20].

Analytical, diagnostic and therapeutic context of Dolichyl mannosyl phosphate


  1. Synthesis of mannosylglucosaminylinositol phospholipids in normal but not paroxysmal nocturnal hemoglobinuria cells. Hirose, S., Ravi, L., Prince, G.M., Rosenfeld, M.G., Silber, R., Andresen, S.W., Hazra, S.V., Medof, M.E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  2. Atypical mannolipids characterize Thy-1-negative lymphoma mutants. Lemansky, P., Gupta, D.K., Meyale, S., Tucker, G., Tartakoff, A.M. Mol. Cell. Biol. (1991) [Pubmed]
  3. Complexity of ethanolamine phosphate addition in the biosynthesis of glycosylphosphatidylinositol anchors in mammalian cells. Kamitani, T., Menon, A.K., Hallaq, Y., Warren, C.D., Yeh, E.T. J. Biol. Chem. (1992) [Pubmed]
  4. Mannosylation of endogenous and exogenous phosphatidic acid by liver microsomal membranes. Formation of phosphatidylmannose. Creek, K.E., Rimoldi, D., Clifford, A.J., Silverman-Jones, C.S., De Luca, L.M. J. Biol. Chem. (1986) [Pubmed]
  5. Effect of energy depletion on the glycosylation of a viral glycoprotein. Datema, R., Schwarz, R.T. J. Biol. Chem. (1981) [Pubmed]
  6. Glycoprotein biosynthesis: studies on thyroid mannosyltransferases. II. Characterization of a polyisoprenyl mannosyl phosphate and evaluation of its intermediary role in the glycosylation of exogenous acceptors. Adamany, A.M., Spiro, R.G. J. Biol. Chem. (1975) [Pubmed]
  7. Biosynthesis of glycoproteins in Candida albicans: solubilization and partial characterization of dolichol phosphate mannose synthase and protein mannosyl transferases. Arroyo-Flores, B.L., Calvo-Méndez, C., Flores-Carreón, A., López-Romero, E. Antonie Van Leeuwenhoek (1998) [Pubmed]
  8. Dolichol phosphate is a rate-limiting factor in mannosyl transferase activity of adult male worms of Schistosoma mansoni. Tempone, A.J., Afonso, A.O., Nascimento, D., Rumjanek, F.D. Mol. Cell. Biochem. (1999) [Pubmed]
  9. Immunogenic properties of mannose-containing ceramide disaccharide and immunochemical detection of its hapten in the two kinds of crustacean, Euphausia superba and Macrobrachium nipponense. Itonori, S., Hiratsuka, M., Sonku, N., Tsuji, H., Itasaka, O., Hori, T., Sugita, M. Biochim. Biophys. Acta (1992) [Pubmed]
  10. Regulation of glycoinositol phospholipid anchor assembly in human lymphocytes. Absent mannolipid synthesis in affected T and natural killer cell lines from paroxysmal nocturnal hemoglobinuria patients. Schubert, J., Schmidt, R.E., Medof, M.E. J. Biol. Chem. (1993) [Pubmed]
  11. Evidence for the stimulation of dolichol and mannolipid synthesis by glucocorticoids in HeLa cells. Ramachandran, C.K., Hignite, C.E., Gray, S.L., Melnykovych, G. Biochem. J. (1981) [Pubmed]
  12. Enzymatic dephosphorylation of dolichyl pyrophosphate--the bacitracin-sensitive, rate-limiting step for dolichyl mannosyl phosphate synthesis in rat liver microsomes. Kato, S., Tsuji, M., Nakanishi, Y., Suzuki, S. Biochem. Biophys. Res. Commun. (1980) [Pubmed]
  13. Distribution of enzymes involved in mannan synthesis in plasma membranes and mesosomal vesicles of Micrococcus lysodeikticus. Owen, P., Salton, M.R. Biochim. Biophys. Acta (1975) [Pubmed]
  14. The biosynthesis of mannolipids and mannose-containing complex glycans by the retina. Kean, E.L. J. Supramol. Struct. (1977) [Pubmed]
  15. Glycoprotein biosynthesis in Chlamydomonas. A mannolipid intermediate with the properties of a short-chain alpha-saturated polyprenyl monophosphate. Lang, W.C. Biochem. J. (1984) [Pubmed]
  16. Characterization of recombinant yeast dolichyl mannosyl phosphate synthase and site-directed mutagenesis of its cysteine residues. Forsee, W.T., McPherson, D., Schutzbach, J.S. Eur. J. Biochem. (1997) [Pubmed]
  17. Entamoeba histolytica: solubilization and biochemical characterization of dolichol phosphate mannose synthase, an essential enzyme in glycoprotein biosynthesis. Villagómez-Castro, J.C., Calvo-Méndez, C., Vargas-Rodríguez, L., Flores-Carreón, A., López-Romero, E. Exp. Parasitol. (1998) [Pubmed]
  18. Mannosylphosphoryldolichol-mediated O-mannosylation of yeast glycoproteins: stereospecificity and recognition of the alpha-isoprene unit by a purified mannosyltransferase. Dotson, S.B., Rush, J.S., Ricketts, A.D., Waechter, C.J. Arch. Biochem. Biophys. (1995) [Pubmed]
  19. Activation of GlcNAc-P-P-dolichol synthesis by mannosylphosphoryldolichol is stereospecific and requires a saturated alpha-isoprene unit. Kean, E.L., Rush, J.S., Waechter, C.J. Biochemistry (1994) [Pubmed]
  20. Glycoprotein biosynthesis in intestinal epithelial cells during differentiation. Incorporation of [14C]mannose from GDP-[14C]mannose into dolichol derivatives. Herscovics, A., Bugge, B. Biochim. Biophys. Acta (1980) [Pubmed]
  21. A novel N-acetylglucosaminyl polyprene in hen oviduct. Hayes, G.R., Lucas, J.J. J. Biol. Chem. (1980) [Pubmed]
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