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S-adenosylmethionine and radical-based catalysis

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Summary.

S-adenosylmthionine is the major methyl donor in all living organisms, but it is also involved in many other reactions occurring through radical-based catalysis. The structure and function of some of these enzymes, including those involved in the synthesis of the molybdenum cofactors, biotin, lipoate, will be discussed.

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References

  • G Agrimi MA Di Noia CMT Marobbio G Fiermonte FM Lasorsa F Palmieri (2004) ArticleTitleIdentification of the human mitochondrial S-adenosylmethionine transporter: bacterial expression, reconstitution, functional characterization and tissue distribution Biochem J 379 183–190 Occurrence Handle14674884 Occurrence Handle10.1042/BJ20031664 Occurrence Handle1:CAS:528:DC%2BD2cXisVyrs7o%3D

    Article  PubMed  CAS  Google Scholar 

  • TP Begley J Xi C Kinsland S Taylor F McLafferty (1999) ArticleTitleThe enzymology of sulphur activation during thiamine and biotin biosynthesis Curr Opin Chem Biol 3 623–629 Occurrence Handle10508664 Occurrence Handle10.1016/S1367-5931(99)00018-6 Occurrence Handle1:CAS:528:DyaK1MXmsleksLg%3D

    Article  PubMed  CAS  Google Scholar 

  • F Berkovitch Y Nicolet JT Wan JT Jarrett CL Drennan (2004) ArticleTitleCrystal structure of biotin synthase, an S-adenosylmethionine-dependent radical enzyme Science 303 76–79 Occurrence Handle14704425 Occurrence Handle10.1126/science.1088493 Occurrence Handle1:CAS:528:DC%2BD3sXhtVWhs7zK

    Article  PubMed  CAS  Google Scholar 

  • RM Cicchillo K-H Lee C Baleanu-Gogonea NM Nesbitt C Krebs SJ Booker (2004) ArticleTitleEscherichia coli lipoyl synthase binds two distinct [4Fe–4S] clusters per polypeptide Biochemistry 43 11770–11781 Occurrence Handle15362861 Occurrence Handle10.1021/bi0488505 Occurrence Handle1:CAS:528:DC%2BD2cXmvFSrtbw%3D

    Article  PubMed  CAS  Google Scholar 

  • E DeMoll W Shive (1983) ArticleTitleThe origin of sulphur in biotin Biochem Biophys Res Commun 110 243–249 Occurrence Handle6340665 Occurrence Handle10.1016/0006-291X(83)91286-X Occurrence Handle1:CAS:528:DyaL3sXhtVCjsLg%3D

    Article  PubMed  CAS  Google Scholar 

  • EC Duin ME Lafferty BR Crouse RM Allen I Sanyaj DH Flint MK Johnson (1997) ArticleTitle[2Fe–2S] to [4Fe–4S] cluster conversion in Escherichia coli biotin synthase Biochemistry 36 11811–11820 Occurrence Handle9305972 Occurrence Handle10.1021/bi9706430 Occurrence Handle1:CAS:528:DyaK2sXlvVCmu74%3D

    Article  PubMed  CAS  Google Scholar 

  • S Dupre G Spoto SP Solinas (1983) ArticleTitleCysteine as precursor and sulphur donor in the biosynthesis of natural sulfur-containing compounds Prog Clin Biol Res 125 343–353 Occurrence Handle6410410 Occurrence Handle1:CAS:528:DyaL3sXkvVGmsbw%3D

    PubMed  CAS  Google Scholar 

  • R Eliasson E Pontis X Sun P Reichard (1994) ArticleTitleAllosteric control of the substrate specificity of the anaerobic ribonucleotide reductase from Escherichia coli J Biol Chem 269 26052–26057 Occurrence Handle7929317 Occurrence Handle1:CAS:528:DyaK2cXmt1Crs7c%3D

    PubMed  CAS  Google Scholar 

  • M Fontecave E Mulliez Ollagnier-de-Choudens (2001) ArticleTitleAdenosylmethionine as a source of 5′-deoxyadenosyl radicals Curr Opin Chem Biol 5 506–511 Occurrence Handle11578923 Occurrence Handle10.1016/S1367-5931(00)00237-4 Occurrence Handle1:CAS:528:DC%2BD3MXntV2gtLs%3D

    Article  PubMed  CAS  Google Scholar 

  • PA Frey OTh Magnusson (2003) ArticleTitleS-adenosylmethionine: a wolf in sheep’s clothing or a rich man’s adenosylcobalamin? Chem Rev 103 2129–2148 Occurrence Handle12797826 Occurrence Handle10.1021/cr020422m Occurrence Handle1:CAS:528:DC%2BD3sXivFGgu7s%3D

    Article  PubMed  CAS  Google Scholar 

  • P Hänzelmann HL Hernandez C Menzel R Garcia-Serres BH Huynh MK Johnson RR Mendel H Schindelin (2004) ArticleTitleCharacterization of MOCS1A, an oxygen-sensitive iron–sulfur protein involved in human molybdenum cofactor biosynthesis J Biol Chem 279 34721–34732 Occurrence Handle15180982 Occurrence Handle10.1074/jbc.M313398200

    Article  PubMed  Google Scholar 

  • P Hänzelmann G Schwarz RR Mendel (2002) ArticleTitleFunctionality of alternative splice forms of the first enzymes involved in human molybdenum cofactor biosynthesis J Biol Chem 277 18303–18312 Occurrence Handle11891227 Occurrence Handle10.1074/jbc.M200947200

    Article  PubMed  Google Scholar 

  • GNL Jameson M Mader Cosper HL Hernandez MK Johnson BH Huynh (2004) ArticleTitleRole of the [2Fe–2S] cluster in recombinant Escherichia coli biotin synthase Biochemistry 43 2022–2031 Occurrence Handle14967042 Occurrence Handle10.1021/bi035666v Occurrence Handle1:CAS:528:DC%2BD2cXnsVGquw%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • JT Jarrett (2003) ArticleTitleThe generation of 5′-deoxyadenosyl radicals by adenosylmethionine-dependent radical enzymes Curr Opin Chem Biol 7 174–182 Occurrence Handle12714049 Occurrence Handle10.1016/S1367-5931(03)00022-X Occurrence Handle1:CAS:528:DC%2BD3sXjtVKgs78%3D

    Article  PubMed  CAS  Google Scholar 

  • SW Jordan JE Cronan SuffixJr (1997) ArticleTitleA new metabolic link. The acyl carrier protein of lipid synthesis donates lipoic acid to the pyruvate dehydrogenase complex in Escherichia coli and mitochondria J Biol Chem 272 17903–17906 Occurrence Handle9218413 Occurrence Handle10.1074/jbc.272.29.17903 Occurrence Handle1:CAS:528:DyaK2sXkslKgtbo%3D

    Article  PubMed  CAS  Google Scholar 

  • G Layer J Moser DW Heinz D Jahn W-D Schubert (2003) ArticleTitleCrystal structure of coproporphyrinogen III oxidase reveals cofactor geometry of radical SAM enzymes EMBO J 22 6214–6224 Occurrence Handle14633981 Occurrence Handle10.1093/emboj/cdg598 Occurrence Handle1:CAS:528:DC%2BD3sXpvVemsLc%3D

    Article  PubMed  CAS  Google Scholar 

  • G Layer K Verfürth E Mahlitz D Jahn (2002) ArticleTitleOxygen-independent coproporphyrinogen-III oxidase HemN from Escherichia coli J Biol Chem 277 34136–34142 Occurrence Handle12114526 Occurrence Handle10.1074/jbc.M205247200 Occurrence Handle1:CAS:528:DC%2BD38Xnt1Sqtrk%3D

    Article  PubMed  CAS  Google Scholar 

  • DT Logan E Mulliez K-M Larsson S Bodevin M Atta PE Garnaud B-M Sjöberg M Fontecave (2003) Proc Natl Acad Sci USA 100 3826–3831 Occurrence Handle12655046 Occurrence Handle10.1073/pnas.0736456100 Occurrence Handle1:CAS:528:DC%2BD3sXivFSqtrk%3D

    Article  PubMed  CAS  Google Scholar 

  • CMT Marobbio G Agrimi FM Lasorsa F Palmieri (2003) ArticleTitleIdentification and functional reconstitution of yeast mitochondrial carrier for S-adenosylmethionine EMBO J 22 5975–5982 Occurrence Handle14609944 Occurrence Handle10.1093/emboj/cdg574 Occurrence Handle1:CAS:528:DC%2BD3sXptVeqt7s%3D

    Article  PubMed  CAS  Google Scholar 

  • A Matthies KV Rajagopalan RR Mendel S Leimkühler (2004) ArticleTitleEvidence for the physiological role of a rhodanese-like protein for the biosynthesis of the molybdenum cofactor in humans Proc Natl Acad Sci USA 101 5946–5951 Occurrence Handle15073332 Occurrence Handle10.1073/pnas.0308191101 Occurrence Handle1:CAS:528:DC%2BD2cXjsFKnsL4%3D

    Article  PubMed  CAS  Google Scholar 

  • JR Miller RW Busby SW Jordan J Cheek TF Henshaw GW Ashley JB Broderick JE Cronan SuffixJr MA Marletta (2000) ArticleTitleEscherichia coli LipA is a lipoylsynthase: in vitro biosynthesis of lipoylated pyruvate dehydrogenase complex from octanoyl-acyl carrier protein Biochemistry 39 15166–15178 Occurrence Handle11106496 Occurrence Handle10.1021/bi002060n Occurrence Handle1:CAS:528:DC%2BD3cXnvVKnsLg%3D

    Article  PubMed  CAS  Google Scholar 

  • T Morikawa R Yasuno H Wada (2001) ArticleTitleDo mammalian cells synthesize lipoic acid? Identification of a mouse cDNA encoding a lipoic acid synthase located in mitochondria FEBS Lett 498 16–21 Occurrence Handle11389890 Occurrence Handle10.1016/S0014-5793(01)02469-3 Occurrence Handle1:CAS:528:DC%2BD3MXktVKrur0%3D

    Article  PubMed  CAS  Google Scholar 

  • S Ollagnier-de-Choudens E Mulliez M Fontecave (2002a) ArticleTitleThe PLP-dependent biotin synthase from Escherichia coli: mechanistic studies FEBS Lett 532 465–468 Occurrence Handle10.1016/S0014-5793(02)03733-X Occurrence Handle1:CAS:528:DC%2BD38XptlCqu74%3D

    Article  CAS  Google Scholar 

  • S Ollagnier-de-Choudens E Mulliez KS Hewitson M Fontecave (2002b) ArticleTitleBiotin synthase is a pyridoxal phosphate-dependent cysteine desulfurase Biochemistry 41 9145–9152 Occurrence Handle10.1021/bi0122011 Occurrence Handle1:CAS:528:DC%2BD38XkvVWhurw%3D

    Article  CAS  Google Scholar 

  • D Padovani E Mulliez M Fontecave (2001) ArticleTitleActivation of class III ribonucleotide reductase by thioredoxin J Biol Chem 276 9587–9589 Occurrence Handle11266436 Occurrence Handle10.1074/jbc.C000895200 Occurrence Handle1:CAS:528:DC%2BD3MXis1OltLg%3D

    Article  PubMed  CAS  Google Scholar 

  • F Pierrel GR Bijörk M Fontecave M Atta (2002) ArticleTitleEnzymatic modification of tRNAs. MiaS is an iron–sulfur protein J Biol Chem 277 13367–13370 Occurrence Handle11882645 Occurrence Handle10.1074/jbc.C100609200 Occurrence Handle1:CAS:528:DC%2BD38XjsFWgtLs%3D

    Article  PubMed  CAS  Google Scholar 

  • F Pierrel T Douki M Fontecave M Atta (2004) ArticleTitleMiaB protein is a bifunctional radical S-adenosylmethionine enzyme involved in thiolation and methylation of tRNA J Biol Chem 279 47555–47563 Occurrence Handle15339930 Occurrence Handle10.1074/jbc.M408562200 Occurrence Handle1:CAS:528:DC%2BD2cXptl2gtbg%3D

    Article  PubMed  CAS  Google Scholar 

  • F Pierrel HL Hernandez MK Johnson M Fontecave M Atta (2003) ArticleTitleMiaB protein from Thermotoga maritima. Characterization of an extremely thermophilic tRNA methyltransferase J Biol Chem 278 29515–29524 Occurrence Handle12766153 Occurrence Handle10.1074/jbc.M301518200 Occurrence Handle1:CAS:528:DC%2BD3sXlvFOgu78%3D

    Article  PubMed  CAS  Google Scholar 

  • DM Pitterle JL Johnson KV Rajagopalan (1993) ArticleTitleIn vitro synthesis of molybdopterin from precursor Z using purified converting factor. Role of protein-bound sulphur in formation of the dithiolene J Biol Chem 268 13506–13509 Occurrence Handle8514783 Occurrence Handle1:CAS:528:DyaK3sXmt1Shsb8%3D

    PubMed  CAS  Google Scholar 

  • DM Pitterle KV Rajagopalan (1993) ArticleTitleThe biosynthesis of molibdopterin in Escherichia coli. Purification and characterization of the converting factor J Biol Chem 268 13499–13505 Occurrence Handle8514782 Occurrence Handle1:CAS:528:DyaK3sXlslKnt78%3D

    PubMed  CAS  Google Scholar 

  • KE Reed JE Cronan SuffixJr (1993) ArticleTitleLipoic acid metabolism in Escherichia coli: sequencing and functional characterization of the lipA and lipB genes J Bacteriol 175 1325–1336 Occurrence Handle8444795 Occurrence Handle1:CAS:528:DyaK3sXit1OisLg%3D

    PubMed  CAS  Google Scholar 

  • J Reiss (2000) ArticleTitleGenetics of molybdenum cofactor deficiency Hum Genet 106 157–163 Occurrence Handle10746556 Occurrence Handle10.1007/s004390051023 Occurrence Handle1:CAS:528:DC%2BD3cXivFaktrw%3D

    Article  PubMed  CAS  Google Scholar 

  • J Reiss E Christensen G Kurlemann M-T Zabot C Dorche (1998) ArticleTitleGenomic structure and mutational spectrum of the bicistronic MOCS1 gene defective in molybdenum cofactor deficiency type A Hum Genet 103 639–644 Occurrence Handle9921896 Occurrence Handle10.1007/s004390050884 Occurrence Handle1:CAS:528:DyaK1cXnvFSjtb0%3D

    Article  PubMed  CAS  Google Scholar 

  • J Reiss S Gross-Hardt E Christensen P Schmidt RR Mendel G Schwarz (2001) ArticleTitleA mutation in the gene for the neurotransmitter receptor-clustering protein gephyrin causes a novel form of molybdenum cofactor deficiency Am J Hum Genet 68 208–213 Occurrence Handle11095995 Occurrence Handle10.1086/316941 Occurrence Handle1:CAS:528:DC%2BD3MXnt1egtA%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • HJ Sofia G Chen BG Hetzler JF Reyes-Spindola NE Miller (2001) ArticleTitleRadical SAM, a novel protein superfamily linking unresolved steps in familiar biosynthetic pathways with radical mechanisms: functional characterization using new analysis and information visualization methods Nucleic Acids Res 29 1097–1106 Occurrence Handle11222759 Occurrence Handle10.1093/nar/29.5.1097 Occurrence Handle1:CAS:528:DC%2BD3MXhvFaqsLw%3D

    Article  PubMed  CAS  Google Scholar 

  • B Stallmeyer G Schwarz J Schulze A Nerlich J Reiss J Kirsch RR Mendel (1999) ArticleTitleThe neurotransmitter receptor-anchoring protein gephyrin reconstitutes molybdenum cofactor biosynthesis in bacteria, plants, and mammalian cells Proc Natl Acad Sci USA 96 1333–1338 Occurrence Handle9990024 Occurrence Handle10.1073/pnas.96.4.1333 Occurrence Handle1:CAS:528:DyaK1MXhsFSrtb4%3D

    Article  PubMed  CAS  Google Scholar 

  • X Sun S Ollagnier PP Schmidt M Atta E Mulliez L Lepape R Eliasson A Gräslund M Fontecave P Reichard B-M Sjöberg (1996) ArticleTitleThe free radical of the anaerobic ribonucleotide reductase from Escherichia coli is at glycine 681 J Biol Chem 271 6827–6831 Occurrence Handle8636106 Occurrence Handle10.1074/jbc.271.12.6827 Occurrence Handle1:CAS:528:DyaK28XhvVyisb8%3D

    Article  PubMed  CAS  Google Scholar 

  • J Tamarit C Gerez C Meier E Mulliez A Trautwein M Fontecave (2000) ArticleTitleThe activating component of the anaerobic ribonucleotide reductase from Escherichia coli. An iron–sulfur center with only three cysteines J Biol Chem 275 15669–15675 Occurrence Handle10821845 Occurrence Handle10.1074/jbc.275.21.15669 Occurrence Handle1:CAS:528:DC%2BD3cXjvFaju7o%3D

    Article  PubMed  CAS  Google Scholar 

  • E Torrents G Buist A Liu R Eliasson J Kok I Gibert A Gräslund P Reichard (2000) ArticleTitleThe anaerobic (Class III) ribonucleotide reductase from Lactococcus lactis. Catalytic properties and allosteric regulation of the pure enzyme system J Biol Chem 275 2463–2471 Occurrence Handle10644700 Occurrence Handle10.1074/jbc.275.4.2463 Occurrence Handle1:CAS:528:DC%2BD3cXpvFCitg%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • B Tse Sum Bui R Benda V Schünemann D Florentin AX Trautwein A Marquet (2003) ArticleTitleFate of the(2Fe–2S)2+ cluster of Escherichia coli biotin synthase during reaction: a Mössbauer characterization Biochemistry 42 8791–8798 Occurrence Handle12873140 Occurrence Handle10.1021/bi034426c

    Article  PubMed  Google Scholar 

  • B Tse Sum Bui M Lotierzo F Escalettes D Florentin A Marquet (2004) ArticleTitleFurther investigation on the turnover of Escherichia coli biotin synthase with dethiobiotin and 9-mercaptodethiobiotin as substrates Biochemistry 43 16432–16441 Occurrence Handle15610037 Occurrence Handle10.1021/bi048040t

    Article  PubMed  Google Scholar 

  • NB Ugulava KK Frederik JT Jarrett (2003) ArticleTitleControl of adenosylmethionine-dependent radical generation in biotin synthase: a kinetic and thermodynamic analysis of substrate binding to active and inactive forms of BioB Biochemistry 42 2708–2719 Occurrence Handle12614166 Occurrence Handle10.1021/bi0261084 Occurrence Handle1:CAS:528:DC%2BD3sXhtFeksro%3D

    Article  PubMed  CAS  Google Scholar 

  • H Wada D Shintani J Ohlrogge (1997) ArticleTitleWhy do mitochondria synthesize fatty acids? Evidence for involvement in lipoic acid production Proc Natl Acad Sci USA 94 1591–1596 Occurrence Handle9037098 Occurrence Handle10.1073/pnas.94.4.1591 Occurrence Handle1:CAS:528:DyaK2sXhtl2mt7k%3D

    Article  PubMed  CAS  Google Scholar 

  • X Zhao JR Miller Y Jiang MA Marletta JE Cronan (2003) ArticleTitleAssembly of the covalent linkage between lipoic acid and its cognate enzymes Chem Biol 10 1293–1302 Occurrence Handle14700636 Occurrence Handle10.1016/j.chembiol.2003.11.016 Occurrence Handle1:CAS:528:DC%2BD3sXhtVWis73J

    Article  PubMed  CAS  Google Scholar 

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  1. Dipartimento di Medicina e Oncologia Sperimentale, Sezione di Biochimica, Università di Torino, Torino, Italy

    M. A. Grillo & S. Colombatto

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  1. M. A. Grillo
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  2. S. Colombatto
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Grillo, M., Colombatto, S. S-adenosylmethionine and radical-based catalysis. Amino Acids 32, 197–202 (2007). https://doi.org/10.1007/s00726-006-0342-x

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