Abstract
Succinimidylferrocenyl propionate (SFP) is introduced as labelling agent for amino functions in peptides and proteins. The resulting derivatives are characterised by considerably lower polarity compared with the native analytes and can thus be well separated by means of reversed phase liquid chromatography (RP-LC). The reaction products are characterised by electrospray ionisation mass spectrometry (ESI-MS) and inductively coupled plasma mass spectrometry (ICP-MS). A further advantage of the method is a simple and straightforward derivatisation protocol. Different basic and acidic model proteins as lysozyme, ß-lactoglobulin A and insulin were derivatised using SFP. Furthermore, the first dual-labelling strategy of thiol and amino groups with ferrocene-based reagents is presented. Whereas the amino groups were derivatised with SFP, the thiol groups were functionalised by reaction with ferrocenecarboxylic acid(2-maleimidoyl)ethylamide. Again, LC/ESI-MS is a suitable tool to characterise the modified peptides and proteins.
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Luo JL, Hammarqvist F, Lind IA, Andersson K, Wernerman K (1995) J Chromatogr B 670:29–36
Bettmer J, Jakubowski N, Prange A (2006) Anal Bioanal Chem 386:7–11
Ahrends R, Pieper S, Kühn A, Weisshoff H, Hamester M, Lindemann T, Scheler T, Lehmann K, Taubner K, Linscheid MW (2007) Mol Cell Proteomics 6:1907–1916
Salmain M, Jaouen G (2003) C R Chimie 6:249–258
El Amouri H, Besace Y, Vaissermann J, Jaouen G (1996) J Organomet Chem 515:103–107
Giese RW, Vallee BL (1972) J Am Chem Soc 94:6199–6200
Peterlik M (1967) Monatsh Chem 98:2133–2134
Tanaka M, Shimada K, Nambara T (1984) J Chromatogr 292:410–411
Shimada K, Orii S, Tanaka M, Nambara T (1986) J Chromatogr 352:329–335
Seiwert B, Henneken H, Karst U (2004) J Am Soc Mass Spectrom 15:1727–1736
Seiwert B, Hayen H, Karst U (2008) J Am Soc Mass Spectrom 19:1–7
Eckert H, Koller M (1990) J Liq Chromatogr 13:3399–3414
Koller M (1990) German Patent 3919317-A1, Chem. Abstr. 115:25536
Anderson GW, Zimmermann JE, Callahan FM (1964) J Am Chem Soc 86:1839–1842
Eckert H, Koller M (1990) Z Naturforsch 45b:1709–1714
Shimada K, Oe T, Tanaka M, Nambara T (1989) J Chromatogr 487:247–255
Cox RL, Schneider TW, Koppang MD (1992) Anal Chim Acta 262:145–159
Bomke S, Seiwert B, Dudek L, Effkemann S, Karst U (2009) Anal Bioanal Chem 393:247–256
van Staveren DR, Metzler-Nolte N (2004) Chem Rev 104:5931–5985
Seiwert B, Karst U (2008) Anal Bioanal Chem 390:181–200
Rosman KJR, Taylor PDP (1999) J Anal At Spectrom 15:5N
Ingle C, Langford N, Harvey L, Dainty JR, Armah C, Fairweather-Tait S, Sharp B, Crews H, Rose M, Lewis J (2002) J Anal At Spectrom 17:1498–1501
Harrington CF, Elahi S, Merson SA, Ponnampalavanar P (2994) J AOAC Int 87:253–258
Takatera K, Watanabe T (1991) Anal Sci 7:695–698
Aňorbe MG, Messerschmidt J, Feldmann I, Jakubowski N (2007) J Anal At Spectrom 22:917–924
Estela del Castillo Busto M, Montes Bayón M, Blanco-González E, Meija J, Sanz-Medel A (2005) Anal Chem 77:5615–5621
Rodríguez SA, Blanco-González E, Alvarez-Llamas G, Montes Bayón M, Sanz-Medel A (2005) Anal Bioanal Chem 383:390–397
Estela del Castillo Busto M, Montes Bayón M, Bettmer J, Sanz-Medel A (2007) Analyst 133:379–384
Marshall PS, Leavens B, Heudi O, Ramirez-Molina C (2004) J Chromatogr A 1056:3–12
Deng A-P, Liu H-T, Jiang S-J, Huang H-J, Ong C-W (2002) Anal Chim Acta 472:55–61
Panchaud A, Hansson J, Affolter M, Rhlid RB, Piu S, Moreillon P, Kussmann M (2008) Mol Cell Proteomics 7:800–812
Lang S, Spratt DE, Guillemette JG, Palmer M (2005) Anal Biochem 342:271–279
Seiwert B, Hayen H, Karst U (2007) Anal Chem 79:7131–7138
Fasman GD (ed) (1989) Practical handbook of biochemistry and molecular biology. CRC, Boca Raton, FL, pp 31
Canfield RE (1962) J Biol Chem 238:2698–2707
Jolles P (1996) Angew Chem Int Ed 8:227–239
Derewenda U, Dodson GG, Diamond R (eds) (1993) Molecular structures in biology. Oxford University Press 260
Conaway-Jacobs A, Lewin LM (1971) Anal Biochem 43:394–400
Brownlow S, Morais Cabral JH, Cooper R, Flower DR, Yewdall SJ, Polikarpov I, North ACT, Sawyer L (1997) Structure 5:481–495
Prange A, Pröfrock D (2008) J Anal Atomic Spectrom 23:432–459
Kahn M (1984) J Pharm Sci 73:1767–1771
Smyth DG, Nagamatsu A, Fruton JS (1960) J Am Chem Soc 82:4600–4604
Seiwert B, Karst U (2007) Anal Bioanal Chem 388:1633–1642
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Financial support by the Fonds der Chemischen Industrie (Frankfurt/Main, Germany) is gratefully acknowledged.
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Bomke, S., Pfeifer, T., Meermann, B. et al. Liquid chromatography with complementary electrospray and inductively coupled plasma mass spectrometric detection of ferrocene-labelled peptides and proteins. Anal Bioanal Chem 397, 3503–3513 (2010). https://doi.org/10.1007/s00216-009-3123-z
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DOI: https://doi.org/10.1007/s00216-009-3123-z