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Lipoylated Peptides and Proteins

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Peptidomimetics II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 49))

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Abstract

Lipoic acid is a heterocyclic sulfur-containing derivative of octanoic acid that is characterized by a 1,2-dithiolane ring. Found in nature as an essential protein cofactor, lipoic acid is implicated in cellular metabolic reactions. In particular, lipoylation is an essential posttranslational modification involved in cellular energetic metabolism performed by mitochondria. In this chapter, we highlight the different pathways to obtain lipoylated peptides and proteins and the antioxidant properties of lipoic acid analogs, including their therapeutic potential in fields such as autoimmunity.

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References

  1. Reed LJ, DeBusk BG, Gunsalus IC, Hornberger CS Jr (1951) Science 114:93–94

    Article  CAS  Google Scholar 

  2. Reed LJ (2001) J Biol Chem 276(42):38329–38336

    Article  CAS  Google Scholar 

  3. Bullock MW, Brockman JA Jr, Patterson EL, Pierce JV, Von Saltza MH, Sanders F, Stoksad ELR (1954) J Am Chem Soc 76:1828–1832

    Article  CAS  Google Scholar 

  4. Blaschke G, Scheidemantel U, Bethge H, Moller R, Beisswenger T, Huthmacher K (1994) Preparation and use of salts of pure enantiomers of alpha-lipoic acid. US Patent 5,281,722, 25 Jan 1994

    Google Scholar 

  5. Reche P, Perham RN (1999) EMBO J 18(10):2673–2682

    Article  CAS  Google Scholar 

  6. Wallis NG, Perham RN (1994) J Mol Biol 236:209–216

    Article  CAS  Google Scholar 

  7. Apweiler R, Hermjakob H, Sharon N (1999) Biochim Biophys Acta 1473:4–8

    Article  CAS  Google Scholar 

  8. Parry RJ (1983) Tetrahedron 39(8):1215–1238

    Article  CAS  Google Scholar 

  9. Cronan JE, Zhao X, Jiang Y (2005) Adv Microb Physiol 50:103–146

    Article  CAS  Google Scholar 

  10. Fujiwara K, Takeuchi S, Okamura-Ikeda K, Motokawa Y (2001) J Biol Chem 276(31):28819–28823

    Article  CAS  Google Scholar 

  11. Fujiwara K, Okamura-Ikeda K, Motokawa Y (1994) J Biol Chem 269(24):16605–16609

    CAS  Google Scholar 

  12. Booker SJ (2004) Chem Biol 11:10–12

    Article  CAS  Google Scholar 

  13. Zhao X, Miller JR, Jiang Y, Marletta MA, Cronan JE (2003) Chem Biol 10(12):1293–1302

    Article  CAS  Google Scholar 

  14. Cicchillo RM, Booker SJ (2005) J Am Chem Soc 127(9):2860–2861

    Article  CAS  Google Scholar 

  15. Miller JR, Busby RW, Jordan SW, Cheek J, Henshaw TF, Ashley GW, Broderick JB, Cronan JE Jr, Marletta MA (2000) Biochemistry 39(49):15166–15178

    Article  CAS  Google Scholar 

  16. Reed LJ (1974) Acc Chem Res 7:40–46

    Article  CAS  Google Scholar 

  17. De Kok A, Hengeveld AF, Martin A, Westphal AH (1998) Biochim Biophys Acta 1385:353–366

    Article  Google Scholar 

  18. Perham RN (1991) Biochemistry 30:8501–8512

    Article  CAS  Google Scholar 

  19. Motokawa Y, Fujiawara K, Okamura-Ikeda K (1995) In: Packer L, Cadenas E (eds) Bithiols in health and disease. Marcel Dekker, New York, pp 389–407

    Google Scholar 

  20. Perham RN (2000) Annu Rev Biochem 69:961–1004

    Article  CAS  Google Scholar 

  21. Valeur E, Bradley M (2009) Chem Soc Rev 38:606–631

    Article  CAS  Google Scholar 

  22. Tuaillon N, Andre C, Briand JP, Penner E, Muller S (1992) J Immunol 148(2):445–450

    CAS  Google Scholar 

  23. Long SA, Quan C, Van de Water J, Nantz MH, Kurth MJ, Barsky D, Colvin ME, Lam KS, Coppel RL, Ansari A, Gershwin ME (2001) J Immunol 167:2956–2963

    Article  CAS  Google Scholar 

  24. Amano K, Leung PSC, Xu Q, Marik J, Quan C, Kurth MJ, Nantz MH, Ansari AA, Lam KS, Zeniya M, Coppel RL, Gershwin ME (2004) J Immunol 172:6444–6452

    Article  CAS  Google Scholar 

  25. Amano K, Leung PSC, Rieger R, Quan C, Wang X, Marik J, Suen YF, Kurth MJ, Nantz MH, Ansari A, Lam KS, Zeniya M, Matsuura E, Coppel RL, Gershwin ME (2005) J Immunol 174:5874–5883

    Article  CAS  Google Scholar 

  26. Rieger R, Leung PSC, Jeddeloh MR, Kurth MJ, Nantz MH, Lam KS, Barsky D, Ansari AA, Coppel L, Mackay IR, Gershwin ME (2006) J Autoimmun 27:7–16

    Article  CAS  Google Scholar 

  27. Naiyanetr P, Butler JD, Meng L, Pfeiff J, Kenny TP, Guggenheim KG, Reiger R, Lam KS, Kurth MJ, Ansari AA, Coppel RL, Lopez-Hoyos M, Gershwin ME, Leung PSC (2011) J Autoimmun 37:209–216

    Article  CAS  Google Scholar 

  28. Chen RCY, Naiyanetr P, Shu SA, Wang J, Yang GX, Kenny TP, Guggenheim KC, Butler JD, Bowlus C, Tao MH, Kurth MJ, Ansari AA, Kaplan M, Coppel RL, Lleo A, Gershwin ME, Leung PSC (2013) Hepatology 57(4):1498–1508

    Article  CAS  Google Scholar 

  29. Kaiser E, Colescott RL, Bossiriger CD, Cook PI (1970) Anal Biochem 34:595–598

    Article  CAS  Google Scholar 

  30. Hancock WS, Battersby JE (1976) Anal Biochem 71:260–264

    Article  CAS  Google Scholar 

  31. Sarin VK, Kent SBH, Tarn JP, Merrifleld RB (1981) Anal Biochem 117:147–157

    Article  CAS  Google Scholar 

  32. Kates SA, Casale RA, Baguisi A, Beeuwkes R III (2014) Bioorg Med Chem 22:505–512

    Article  CAS  Google Scholar 

  33. Brookfield DC, Green J, Ali ST, Machado RS, Guest JR (1991) FEBS Lett 295:13–16

    Article  CAS  Google Scholar 

  34. Quinn J, Diamond AG, Masters AK, Brookfield DE, Wallis NG, Yeaman SJ (1993) Biochem J 289:81–85

    Article  CAS  Google Scholar 

  35. Green DE, Morris TW, Green J, Cronan JE Jr, Guest JR (1995) Biochem J 309:853–862

    Article  CAS  Google Scholar 

  36. Bryant P, Kriek M, Wood RJ, Roach PL (2006) Anal Biochem 351:44–49

    Article  CAS  Google Scholar 

  37. Nawa H, Brady WT, Koike M, Reed LJ (1960) J Am Chem Soc 82:896–903

    Article  CAS  Google Scholar 

  38. Reed LJ, Koike M, Levitch ME, Leach FR (1958) J Biol Chem 232:143–158

    CAS  Google Scholar 

  39. Vaughan JR Jr (1952) J Am Chem Soc 74:6137–6139

    Article  CAS  Google Scholar 

  40. Thomas RC, Reed LJ (1956) J Am Chem Soc 78:6148–6149

    Article  CAS  Google Scholar 

  41. Matsugo S, Yasui F, Ozaki T (2003) ITE Lett Batteries New Technol Med 4(2):206–210

    CAS  Google Scholar 

  42. Brufani M, Medici I, Bettolo RM, Migneco LM, Marzella R, Figliola R, LaBella A (2011) Alpha lipoic acid derivatives and their use in drug preparation. US Patent 2011/0212954A1, 1 Sept 2011

    Google Scholar 

  43. Koufaki M, Kiziridi C, Alexi X, Alexis MN (2009) Bioorg Med Chem 17(17):6432–6441

    Article  CAS  Google Scholar 

  44. Koufaki M, Kiziridi C, Nikoloudaki F, Alexis MN (2007) Bioorg Med Chem Lett 17(15):4223–4227

    Article  CAS  Google Scholar 

  45. Guillonneau C, Charton Y, Ginot YM, Fouquier-d’Herouel MV, Bertrand M, Lockhart B, Lestage P, Goldstein S (2003) Eur J Med Chem 38:1–11

    Article  CAS  Google Scholar 

  46. Rentier C, Pacini G, Nuti F, Peroni E, Rovero P, Papini AM (2015) J Pept Sci 21:408–414

    Article  CAS  Google Scholar 

  47. Kisfaludy L, Schon I (1983) Synthesis 4:325–327

    Article  Google Scholar 

  48. Fries M, Jung HI, Perham RN (2003) Biochemistry 42(23):6996–7002

    Article  CAS  Google Scholar 

  49. Sheng X, Liu Y (2013) Biochemistry 52(45):8079–8093

    Article  CAS  Google Scholar 

  50. Graham LD, Packman LC, Perham RN (1989) Biochemistry 28(4):1574–1581

    Article  CAS  Google Scholar 

  51. Gunsalus IC, Barton LS, Gruber W (1956) J Am Chem Soc 78(8):1763–1766

    Article  CAS  Google Scholar 

  52. Susumu K, Uyeda T, Mednitz IL, Pons T, Delehanty JB, Mattoussi H (2007) J Am Chem Soc 129:13987–13996

    Article  CAS  Google Scholar 

  53. Fang Z, Liu L, Xu L, Yin X, Zhong X (2008) Nanotechnology 19:235603–235609

    Article  Google Scholar 

  54. Cleland WW (1964) Biochemistry 3(4):480–482

    Article  CAS  Google Scholar 

  55. Burns JA, Butler JC, Moran J, Whitesides GM (1991) J Org Chem 56:2648–2650

    Article  CAS  Google Scholar 

  56. Getz EB, Xiao M, Chakrabarty T, Cooke R, Selvin PR (1999) Anal Biochem 273:73–80

    Article  CAS  Google Scholar 

  57. Palui G, Avellini T, Zhan N, Pan F, Gray D, Alabugin I, Mattoussi H (2012) J Am Chem Soc 134(39):16370–16378

    Article  CAS  Google Scholar 

  58. Thomas RC, Reed LJ (1956) J Am Chem Soc 78(23):6148–6149

    Article  CAS  Google Scholar 

  59. Brown PR, Edwards JO (1969) J Org Chem 34(10):3131–3135

    Article  CAS  Google Scholar 

  60. Willey TM, Vance AL, Bostedt C, van Buuren T, Meulenberg RW, Terminello LJ, Fadley CS (2004) Langmuir 20:4939–4944

    Article  CAS  Google Scholar 

  61. Su D, Yang X, Xia Q, Chai F, Wang C, Qu F (2013) RSC Adv 3:24618–24624

    Article  CAS  Google Scholar 

  62. Nikolic RS, Krstic NS, Nikolic GM, Kocic GM, Cakic MD, Andelkovic DH (2014) Polyhedron 80:223–227

    Article  CAS  Google Scholar 

  63. Suh JH, Moreau R, Heath SH, Hagen TM (2005) Redox Rep 10(1):52–60

    Article  CAS  Google Scholar 

  64. Ou P, Tritschler HJ, Wolff SP (1995) Biochem Pharmacol 50:123–126

    Article  CAS  Google Scholar 

  65. Sigel H, Prijs B, McCormick DB, Shih JCH (1978) Arch Biochem Biophys 187:208–214

    Article  CAS  Google Scholar 

  66. Veljkovic AR, Nikolic RS, Kocic GM, Pavlovic DD, Cvetkovic TP, Sokolovic DT, Jevtovic TM, Basic JT, Laketic DM, Marinkovic MR, Stojanovic SR, Djordjevic BS, Krsmanovic MM (2012) Renal Failure 34(10):1281–1287

    Article  CAS  Google Scholar 

  67. Ioannou PV, Tsivgoulis GM (2014) Monatsh Chem 145:897–909

    Article  CAS  Google Scholar 

  68. Smith AR, Shenvi SV, Widlansky M, Suh JH, Hagen TM (2004) Curr Med Chem 11(9):1135–1146

    Article  CAS  Google Scholar 

  69. Packer L, Witt EH, Tritschler HJ (1995) Free Radical Biol Med 19:227–250

    Article  CAS  Google Scholar 

  70. Tomassoni D, Amenta F, Amantini C, Farfariello V, Manelli LDC, Nwankwo IE, Marini C, Tayebati SK (2013) Int J Mol Sci 14:4580–4595

    Article  CAS  Google Scholar 

  71. Heinisch BB, Francesconi M, Mittermayer F, Schaller G, Gouya G, Wolzt M, Pleiner J (2010) Eur J Clin Invest 40(2):148–154

    Article  CAS  Google Scholar 

  72. Ziegler D, Nowak H, Kempler P, Vargha P, Low PA (2004) Diabet Med 21(2):114–121

    Article  CAS  Google Scholar 

  73. Morini M, Roccatagliata L, Dell’Eva R, Pedemonte E, Furlan R, Minghelli S, Giunti D, Pfeffer U, Marchese M, Noonan D, Mancardi G, Albini A, Uccelli A (2004) J Neuroimmunol 148:146–153

    Article  CAS  Google Scholar 

  74. Yadav Y, Marracci GH, Munar MY, Cherala G, Stuber LE, Alvarez L, Shinto L, Koop DR, Bourdette DN (2010) Mult Scler 16(4):387–397

    Article  CAS  Google Scholar 

  75. Holmquist L, Stuchbury G, Berbaum K, Muscat S, Young S, Hager K, Engel J, Munch G (2007) Pharmacol Ther 113:154–164

    Article  CAS  Google Scholar 

  76. Maczurek A, Hager K, Kenklies M, Sharman M, Martins R, Engel J, Carlson DA, Munch G (2008) Adv Drug Delivery Rev 60:1463–1470

    Article  CAS  Google Scholar 

  77. Wang X, Nagata K, Higuchi M (2012) Thin Solid Films 520:2884–2891

    Article  CAS  Google Scholar 

  78. Tappura K, Vikholm-Lundin I, Albers WM (2007) Biosens Bioelectron 22:912–919

    Article  CAS  Google Scholar 

  79. Gatto E, Venanzi M (2013) Polym J 45:468–480

    Article  CAS  Google Scholar 

  80. Xianhua L, Jiaofeng Y, Lin Z, Hongxi L, Yiren L (2013) Trans Tianjin Univ 19:248–254

    Article  Google Scholar 

  81. Wen X, Linton RW, Formaggio F, Toniolo C, Samulski ET (2004) J Phys Chem A 108:9673–9681

    Article  CAS  Google Scholar 

  82. Matulaitiene I, Kuodis Z, Eicher-Lorka O, Niaura G (2013) J Electroanal Chem 700:77–85

    Article  CAS  Google Scholar 

  83. Blonder R, Willner I, Bückmann AF (1998) J Am Chem Soc 120:9335–9341

    Article  CAS  Google Scholar 

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Acknowledgments

ANR Chaire d’Excellence PeptKit 2009–2014 (grant n° ANR-09-CEXC-013-01), French-Italian University (Vinci Project grant n° C2-133), and Ente Cassa di Risparmio di Firenze are gratefully acknowledged for their financial support.

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Correspondence to Anna-Maria Papini .

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Rentier, C., Pacini, G., Nuti, F., Rovero, P., Papini, AM. (2015). Lipoylated Peptides and Proteins. In: Lubell, W. (eds) Peptidomimetics II. Topics in Heterocyclic Chemistry, vol 49. Springer, Cham. https://doi.org/10.1007/7081_2015_186

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