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
Reed LJ, DeBusk BG, Gunsalus IC, Hornberger CS Jr (1951) Science 114:93–94
Reed LJ (2001) J Biol Chem 276(42):38329–38336
Bullock MW, Brockman JA Jr, Patterson EL, Pierce JV, Von Saltza MH, Sanders F, Stoksad ELR (1954) J Am Chem Soc 76:1828–1832
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
Reche P, Perham RN (1999) EMBO J 18(10):2673–2682
Wallis NG, Perham RN (1994) J Mol Biol 236:209–216
Apweiler R, Hermjakob H, Sharon N (1999) Biochim Biophys Acta 1473:4–8
Parry RJ (1983) Tetrahedron 39(8):1215–1238
Cronan JE, Zhao X, Jiang Y (2005) Adv Microb Physiol 50:103–146
Fujiwara K, Takeuchi S, Okamura-Ikeda K, Motokawa Y (2001) J Biol Chem 276(31):28819–28823
Fujiwara K, Okamura-Ikeda K, Motokawa Y (1994) J Biol Chem 269(24):16605–16609
Booker SJ (2004) Chem Biol 11:10–12
Zhao X, Miller JR, Jiang Y, Marletta MA, Cronan JE (2003) Chem Biol 10(12):1293–1302
Cicchillo RM, Booker SJ (2005) J Am Chem Soc 127(9):2860–2861
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
Reed LJ (1974) Acc Chem Res 7:40–46
De Kok A, Hengeveld AF, Martin A, Westphal AH (1998) Biochim Biophys Acta 1385:353–366
Perham RN (1991) Biochemistry 30:8501–8512
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
Perham RN (2000) Annu Rev Biochem 69:961–1004
Valeur E, Bradley M (2009) Chem Soc Rev 38:606–631
Tuaillon N, Andre C, Briand JP, Penner E, Muller S (1992) J Immunol 148(2):445–450
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
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
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
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
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
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
Kaiser E, Colescott RL, Bossiriger CD, Cook PI (1970) Anal Biochem 34:595–598
Hancock WS, Battersby JE (1976) Anal Biochem 71:260–264
Sarin VK, Kent SBH, Tarn JP, Merrifleld RB (1981) Anal Biochem 117:147–157
Kates SA, Casale RA, Baguisi A, Beeuwkes R III (2014) Bioorg Med Chem 22:505–512
Brookfield DC, Green J, Ali ST, Machado RS, Guest JR (1991) FEBS Lett 295:13–16
Quinn J, Diamond AG, Masters AK, Brookfield DE, Wallis NG, Yeaman SJ (1993) Biochem J 289:81–85
Green DE, Morris TW, Green J, Cronan JE Jr, Guest JR (1995) Biochem J 309:853–862
Bryant P, Kriek M, Wood RJ, Roach PL (2006) Anal Biochem 351:44–49
Nawa H, Brady WT, Koike M, Reed LJ (1960) J Am Chem Soc 82:896–903
Reed LJ, Koike M, Levitch ME, Leach FR (1958) J Biol Chem 232:143–158
Vaughan JR Jr (1952) J Am Chem Soc 74:6137–6139
Thomas RC, Reed LJ (1956) J Am Chem Soc 78:6148–6149
Matsugo S, Yasui F, Ozaki T (2003) ITE Lett Batteries New Technol Med 4(2):206–210
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
Koufaki M, Kiziridi C, Alexi X, Alexis MN (2009) Bioorg Med Chem 17(17):6432–6441
Koufaki M, Kiziridi C, Nikoloudaki F, Alexis MN (2007) Bioorg Med Chem Lett 17(15):4223–4227
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
Rentier C, Pacini G, Nuti F, Peroni E, Rovero P, Papini AM (2015) J Pept Sci 21:408–414
Kisfaludy L, Schon I (1983) Synthesis 4:325–327
Fries M, Jung HI, Perham RN (2003) Biochemistry 42(23):6996–7002
Sheng X, Liu Y (2013) Biochemistry 52(45):8079–8093
Graham LD, Packman LC, Perham RN (1989) Biochemistry 28(4):1574–1581
Gunsalus IC, Barton LS, Gruber W (1956) J Am Chem Soc 78(8):1763–1766
Susumu K, Uyeda T, Mednitz IL, Pons T, Delehanty JB, Mattoussi H (2007) J Am Chem Soc 129:13987–13996
Fang Z, Liu L, Xu L, Yin X, Zhong X (2008) Nanotechnology 19:235603–235609
Cleland WW (1964) Biochemistry 3(4):480–482
Burns JA, Butler JC, Moran J, Whitesides GM (1991) J Org Chem 56:2648–2650
Getz EB, Xiao M, Chakrabarty T, Cooke R, Selvin PR (1999) Anal Biochem 273:73–80
Palui G, Avellini T, Zhan N, Pan F, Gray D, Alabugin I, Mattoussi H (2012) J Am Chem Soc 134(39):16370–16378
Thomas RC, Reed LJ (1956) J Am Chem Soc 78(23):6148–6149
Brown PR, Edwards JO (1969) J Org Chem 34(10):3131–3135
Willey TM, Vance AL, Bostedt C, van Buuren T, Meulenberg RW, Terminello LJ, Fadley CS (2004) Langmuir 20:4939–4944
Su D, Yang X, Xia Q, Chai F, Wang C, Qu F (2013) RSC Adv 3:24618–24624
Nikolic RS, Krstic NS, Nikolic GM, Kocic GM, Cakic MD, Andelkovic DH (2014) Polyhedron 80:223–227
Suh JH, Moreau R, Heath SH, Hagen TM (2005) Redox Rep 10(1):52–60
Ou P, Tritschler HJ, Wolff SP (1995) Biochem Pharmacol 50:123–126
Sigel H, Prijs B, McCormick DB, Shih JCH (1978) Arch Biochem Biophys 187:208–214
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
Ioannou PV, Tsivgoulis GM (2014) Monatsh Chem 145:897–909
Smith AR, Shenvi SV, Widlansky M, Suh JH, Hagen TM (2004) Curr Med Chem 11(9):1135–1146
Packer L, Witt EH, Tritschler HJ (1995) Free Radical Biol Med 19:227–250
Tomassoni D, Amenta F, Amantini C, Farfariello V, Manelli LDC, Nwankwo IE, Marini C, Tayebati SK (2013) Int J Mol Sci 14:4580–4595
Heinisch BB, Francesconi M, Mittermayer F, Schaller G, Gouya G, Wolzt M, Pleiner J (2010) Eur J Clin Invest 40(2):148–154
Ziegler D, Nowak H, Kempler P, Vargha P, Low PA (2004) Diabet Med 21(2):114–121
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
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
Holmquist L, Stuchbury G, Berbaum K, Muscat S, Young S, Hager K, Engel J, Munch G (2007) Pharmacol Ther 113:154–164
Maczurek A, Hager K, Kenklies M, Sharman M, Martins R, Engel J, Carlson DA, Munch G (2008) Adv Drug Delivery Rev 60:1463–1470
Wang X, Nagata K, Higuchi M (2012) Thin Solid Films 520:2884–2891
Tappura K, Vikholm-Lundin I, Albers WM (2007) Biosens Bioelectron 22:912–919
Gatto E, Venanzi M (2013) Polym J 45:468–480
Xianhua L, Jiaofeng Y, Lin Z, Hongxi L, Yiren L (2013) Trans Tianjin Univ 19:248–254
Wen X, Linton RW, Formaggio F, Toniolo C, Samulski ET (2004) J Phys Chem A 108:9673–9681
Matulaitiene I, Kuodis Z, Eicher-Lorka O, Niaura G (2013) J Electroanal Chem 700:77–85
Blonder R, Willner I, Bückmann AF (1998) J Am Chem Soc 120:9335–9341
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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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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DOI: https://doi.org/10.1007/7081_2015_186
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