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2008 | 55 | 4 |

Tytuł artykułu

Prenyl sulfates as alkylating reagents for mercapto amino acids

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
A new methodology for prenylation of thiol compounds has been developed. The approach is based on the use of prenyl sulfates as new reagents for S-prenylation of benzenethiol and cysteamine in aqueous systems. The C10-prenols geraniol and nerol that differ in the configuration (E or Z, correspondingly) of the α-isoprene unit were efficiently O-sulfated in the presence of a pyridine-SO3,complex. The obtained geranyl and neryl sulfates were tested as alkylating agents. These compounds were chosen to reveal the influence of the α-isoprene unit configuration on their alkylation (prenylation) ability. S-Geranyl cysteine was prepared to demonstrate the applicability of this method for prenylation of peptides containing mercapto amino acids.

Wydawca

-

Rocznik

Tom

55

Numer

4

Opis fizyczny

p.807-813,fig.,ref.

Twórcy

autor
  • Russian Academy of Sciences, Leninsky prospect 47, Moscow, 119991, Russian Federation
autor
autor
autor
autor
autor

Bibliografia

  • Abankwa D, Gorfe AA, Hancock JF (2007) Ras nanoclusters: Molecular structure and assembly. Semin Cell Dev Biol 18:599-607.
  • Baron RA, Seabra MC (2008) Rab geranylgeranylation occurs preferentially via the pre-formed REP:RGGT complex and is regulated by geranylgeranyl pyrophosphate. Biochem J 415:67-75.
  • Brunsveld L, Watzke A, Durek T, Alexandrov K, Goody RS, Waldmann H (2005) Synthesis of functionalized Rab GTPases by a combination of solution- or solid-phase lipopeptide synthesis. Chemistry 11:2756-2772.
  • Brunsveld L, Kuhlman J, Alexandrov K, Wittinghofer A, Goody RS, Waldmann H (2006) Lipidated Ras and Rab proteins-synthesis, structure, and function. Angew Chem Int Ed Engl 45:6622-6646.
  • Buday L, Downward J (2008) Many faces of Ras activation. Biochim Biophys Acta 1786:178-187.
  • Crombie L, King RW, Whiting DA (1975) Carbon-13-magnetic resonance spectra. Synthetic presqualene esters, related cyclopropanes, and isoprenoids. J Chem Soc Perkin Trans 1:913-915.
  • Eisenberg S, Henis YI (2008) Interactions of Ras proteins with the plasma membrane and their roles in signaling. Cell Signal 20:31-39.
  • Epstein WW, Lever D, Leining LM, Bruenger E, Rilling HC (1991) Quantitation of prenylcysteines by a selective cleavage reaction. Proc Natl Acad Sci USA 88:9668-9670.
  • Farnsworth CC, Kawata M, Yoshida Y, Takai Y, Gelb MH, Glomset JA (1991) C terminus of the small GTP-binding protein smg p25A contains two geranylgeranylated cysteine residues and a methyl ester. Proc Natl Acad Sci USA 88:6196-6200.
  • Galichet A, Gruissem W (2006) Developmentally controlled farnesylation modulates AtNAP1;1 function in cell proliferation and cell expansion during Arabidopsis leaf development. Plant Physiol 142:1412-1426.
  • Gutkowska M, Bienkowski T, Hung VS, Wanke M, Hertel J, Danikiewicz W, Swiezewska E (2004) Proteins are polyisoprenylated in Arabidopsis thaliana. Biochem Biophys Res Commun 322:998-1004.
  • Hancock JF, Magee AL, Childs JE, Marshall CL (1989) All ras proteins are polyisoprenylated but only some are palmitoylated. Cell 57:1167-1177.
  • Kadereit D, Deck P, Heinemann I, Waldmann H (2001) Acid-labile protecting groups for the synthesis of lipidated peptides. Chemistry 7:1184-1193.
  • Kamiya Y, Sakuai A, Tamura S, Takahashi N (1978) Structure of rhodotorucine A, a novel lipopeptide, inducing mating tube formation in Rhodosporidium toruloides. Biochem Biophys Res Commun 83:1077-1083.
  • Kragol G, Lumbierres M, Palomo JM, Waldmann H (2004) Solid-phase synthesis of lipidated peptides. Angew Chem Int Ed Engl 43:5839-5842.
  • Kuhn K, Owen DJ, Bades B, Wittinghofer A, Kuhlmann J, Waldmann H (2001) Synthesis of fluorescent functional Ras lipoproteins and fluorescent derivatives. J Am Chem Soc 123:1023-1035.
  • Lane KT, Beese LS (2006) Thematic review series: lipid posttranslational modifications. Structural biology of protein farnesyltransferase and geranylgeranyltransferase type I. J Lipid Res 47:681-699.
  • Ludolph B, Eisele F, Waldmann H (2002) Solution- and solid-phase synthesis of the polybasic lipid-modified C termini of Rho A and K-Ras 4B. Chembiochem 3:901-904.
  • Ludolph B, Waldmann H (2003) The synthesis of acid- and base-labile lipopeptides on solid support. Chemistry 9:3683-3691.
  • Lumbierres M, Palomo JM, Kragol G, Roehrs S, Muller O, Waldmann H (2005) Solid-phase synthesis of lipidated peptides. Chemistry 11:7405-7415.
  • Maltsev SD, Sizova OV, Danilov LL, Shibaev VN (2001) Synthesis of dolichyl and polyprenyl sulfates. Russ J Bioorganic Chem 27:400-403 (Engl Transl).
  • Naider FR, Becker JM (1997) Synthesis of prenylated peptides and peptide esters.Biopolymers 43:3-14.
  • Omer CA, Gibbs JB (1994) Protein prenylation in eukariotic microorganisms: genetics, biology and biochemistry. Mol Microbiol 11:219-225.
  • Patra SK (2008) Ras regulation of DNA-methylation and cancer. Exp Cell Res 314:1193-1201.
  • Pechlivanis M, Kuhlmann J (2006) Hydrophobic modifications of Ras proteins by isoprenoid groups and fatty acids - More than just membrane anchoring. Biochim Biophys Acta 1764:1914-1931.
  • Perez-Sala D (2007) Protein isoprenylation in biology and disease: general overview and perspectives from studies with genetically engineered animals. Front Biosci 12:4456-4472.
  • Reents R, Wagner M, Schlummer S, Kuhlmann J, Waldmann H (2005) Synthesis and application of fluorescent Ras proteins for live-cell imaging. Chembiochem 6:86-94.
  • Rilling HC, Bruenger E, Epstein WW, Crain PF (1990) Prenylated proteins: the structure of the isoprenoid group. Science 247:318-320.
  • Rodriguez-Concepcion M, Yalovsky S, Gruissem W (1999) Protein prenylation in plants: old friends and new targets. Plant Mol Biol 39:865-870.
  • Schroeder H, Leventis R, Rex S, Schelhaas M, Nogele E, Waldmann H, Silvius JR (1997) S-acylation and plasma membrane targeting of the farnesylated carboxyl-terminal peptide of N-Ras in mammalian fibroblasts. Biochemistry 36:13102-13109.
  • Shahinian S, Silvius JR (1995) Doubly-lipid modified protein sequence motifs exhibit long-lived anchorage to lipid bilayer membranes. Biochemistry 34:3813-3822.
  • Shipton CA, Parmryd I, Swiezewska E, Andersson B, Dallner G (1995) Isoprenylation of plant proteins in vivo. J Biol Chem 270:566-572.
  • Silvius JR, Lheureux F (1994) Fluorimetric evaluation of the affinities of isoprenylated peptides for lipid bilayers. Biochemistry 33:3014-3022.
  • Simonen M, Ibig-Rehm Y, Hofmann G, Zimmermann J, Albrecht G, Magnier M, Heidinger V, Gabriel D (2008) High-content assay to study protein prenylation. J Biomol Screen 13:456-467.
  • Swiezewska E, Thelin A, Dallner G, Andersson B, Ernster L (1993) Occurrence of prenylated proteins in plant cells. Biochem Biophys Res Commun 192:161-166.
  • Takai Y, Sasaki T, Matozaki T (2001) Small GTP-binding proteins. Physiol Rev 81:153-208.
  • Vogler O, Barcelo JM, Ribas C, Escriba PV (2008) Membrane interactions of G proteins and other related proteins. Biochim Biophys Acta 1778:1640-1652.
  • Volkert M, Wagner M, Peters C, Waldman H (2001) The chemical biology of ras lipidation. Biol Chem 382:1133-1145.
  • Wittinghofer A, Waldmann H (2000) Ras - a molecular switch involved in tumor formation. Angew Chem Int Ed Engl 39:4192-4214.
  • Xue CB, Becker JM, Naider FR (1992) Efficient regioselective isoprenylation of peptides in acidic aqueous solution using zinc acetate as catalyst. Tetrahedron Lett 33:1435-1438

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

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