Simultaneous analysis of the non-canonical amino acids norleucine and norvaline in biopharmaceutical-related fermentation processes by a new ultra-high performance liquid chromatography approach
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- 作者：Michael Biermann (1)
Bettina Bardl (1)
Sebastian Vollst?dt (1)
Julia Linnemann (1)
Uwe Knüpfer (1)
Guido Seidel (2)
Uwe Horn (1) - 关键词：Recombinant antibody ; Norleucine ; Norvaline ; Ultra ; high performance liquid chromatography ; Biopharmaceutical fermentation ; Escherichia coli ; Bioprocess design
- 刊名：Amino Acids
- 出版年：2013
- 出版时间：April 2013
- 年：2013
- 卷：44
- 期：4
- 页码：1225-1231
- 全文大小：280KB
- 参考文献：1. Ahmed I, Kaspar B, Sharma U (2012) Biosimilars: impact of biologic product life cycle and European experience on the regulatory trajectory in the United States. Clin Ther 34(2):400-19 CrossRef
2. Apostol I, Lippincott J, Levine J, Leach J, Hess E, Glascock CB, Weickert MJ, Blackmore R (1997) Incorporation of norvaline at leucine positions in recombinant human hemoglobin expressed in / Escherichia coli. J Biol Chem 272:28980-8988 CrossRef
3. Armenta JM, Cortes DF, Pisciotta JM, Shuman JL, Blakeslee K, Rasoloson D, Ogunbiyi O, Sullivan DJ Jr, Shulaev V (2010) Sensitive and rapid method for amino acid quantitation in malaria biological samples using AccQ.Tag ultra performance liquid chromatography–electrospray ionization–MS/MS with multiple reaction monitoring. Anal Chem 82(2):548-58 CrossRef
4. Arrieta MP, Prats-Moya MS (2012) Free amino acids and biogenic amines in Alicante Monastrell wines. Food Chem 135(3):1511-519 CrossRef
5. Berkowitz SA, Engen JR, Mazzeo JR, Jones GB (2012) Analytical tools for characterizing biopharmaceuticals and the implications for biosimilars. Nat Rev Drug Discov 11(7):527-40 CrossRef
6. Bogosian G, Violand BN, Dorward-King EJ, Workman WE, Jung PE, Kane JF (1989) Biosynthesis and incorporation into protein of norleucine by / Escherichia coli. J Biol Chem 264:531-39
7. Budisa N, Steipe B, Demange P, Eckerskorn C, Kellermann J, Huber R (1995) High-level biosynthetic substitution of methionine in proteins by its analogs 2-aminohexanoic acid, selenomethionine, telluromethionine and ethionine in / Escherichia coli. Eur J Biochem 230:788-96 CrossRef
8. Dettmer K, Stevens AP, Fagerer SR, Kaspar H, Oefner PJ (2012) Amino acid analysis in physiological samples by GC–MS with propyl chloroformate derivatization and iTRAQ–LC–MS/MS. Methods Mol Biol 828:165-81 CrossRef
9. Fekete S, Oláh E, Fekete J (2012) Fast liquid chromatography: the domination of core–shell and very fine particles. J Chromotogr A 1228:57-1 CrossRef
10. Fekkes D (1996) State-of-the-art of high-performance liquid chromatographic analysis of amino acids in physiological samples. J Chromatogr B 682:3-2 CrossRef
11. Gritti F, Guiochon G (2012) The current revolution in column technology: how it began, where is it going? J Chromotogr A 1228:2-9 CrossRef
12. Guiochon G, Gritti F (2011) Shell particles, trials, tribulations and triumphs. J Chromotogr A 1218(15):1915-938 CrossRef
13. Habicht G, Haupt C, Friedrich RP, Hortschansky P, Sachse C, Meinhardt J, Wieligmann K, Gellermann GP, Brodhun M, G?tz J, Halbhuber KJ, R?cken C, Horn U, F?ndrich M (2007) Directed selection of a conformational antibody domain that prevents mature amyloid fibril formation by stabilizing Aβ protofibrils. Proc Natl Acad Sci USA 104(49):19232-9237 CrossRef
14. Horn U, Strittmatter W, Krebber A, Knüpfer U, Kujau R, Wenderoth R, Müller C, Matzku S, Plückthun A, Riesenberg D (1996) High volumetric yields of functional dimeric miniantibodies in / Escherichia coli using an optimized expression vector and high cell density fermentation under non-limited growth conditions. Appl Microbiol Biotechnol 46:524-32 CrossRef
15. Husek P, Simek P, Hartvich P, Zahradnickova H (2008) Fluoroalkyl chloroformates in treating amino acids for gas chromatographic analysis. J Chromatogr A 1186:391-00 CrossRef
16. Ilisz I, Aranyi A, Pataj Z, Péter A (2012) Enantiomeric separation of nonproteinogenic amino acids by high-performance liquid chromatography. J Chromotogr A. doi:10.1016/j.chroma.2012.07.011
17. Joseph MH, Davies P (1983) Electrochemical activity of / o-phthalaldehyde mercaptoethanol derivatives of amino acids: application to high-performance liquid chromatographic determination of amino acids in plasma and other biological materials. J Chromatogr 277:125-36 CrossRef
18. Kaspar H, Dettmer K, Gronwald W, Oefner PJ (2009) Advances in amino acid analysis. Anal Bioanal Chem 393(2):445-52 CrossRef
19. Kisumi M, Sugiura M, Kato J, Chibata I (1976) l- Norvaline and l- homoisoleucine formation by / Serratia marcescens. J Biochem 79(5):1021-028
20. Kohlhaw G, Leary TR, Umbarger HE (1969) Alpha-isopropylmalate synthase from / Salmonella typhimurium. Purification and properties. J Biol Chem 244:2218-225
21. Kroemer O (2005) OPA amino acids on Gemini C18. Phenomenex application note ID: 15992
22. Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L (1997) Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem 43:1421-428
23. Lu HS, Tsai LB, Kenney WC, Lai PH (1988) Identification of unusual replacement of methionine by norleucine in recombinant interleukin-2 produced by / E. coli. Biochem Biophys Res Commun 156:807-13 CrossRef
24. Mayer HK, Fiechter G, Fischer E (2010) A new ultra-pressure liquid chromatography method for the determination of biogenic amines in cheese. J Chromotogr A 1217(19):3251-257 CrossRef
25. Molnár-Perl I (2005) HPLC of amino acids as / o-phthalaldehyde derivatives. J Chromotogr Libr 70:163-98 CrossRef
26. Nandi P, Sen GP (1953) An antifungal substance from a strain of / Bacillus subtilis. Nature 172:871-72 CrossRef
27. Pappa-Louisi A, Nikitas P, Agrafiotou P, Papageorgiou A (2007) Optimization of separation and detection of 6-aminoquinolyl derivatives of amino acids by using reversed-phase liquid chromatography with on line UV, fluorescence and electrochemical detection. Anal Chim Acta 593:92-7 CrossRef
28. Pereira V, Pontes M, Camara JS, Marques JC (2008) Simultaneous analysis of free amino acids and biogenic amines in honey and wine samples using in loop orthophthalaldehyde derivatization procedure. J Chromotogr A1189(1-):435-43
29. Reynolds NM, Lazazzera BA, Ibba M (2010) Cellular mechanisms that control mistranslation. Nat Rev Microbiol 12:849-56 CrossRef
30. Roth M (1971) Fluorescence reaction for amino acids. Anal Chem 43(7):880-82 CrossRef
31. Soini J, Falschlehner C, Liedert C, Bernhardt J, Vuoristo J, Neubauer P (2008) Norvaline is accumulated after a down-shift of oxygen in / Escherichia coli W3110. Microb Cell Fact 7:30 CrossRef
32. Song Y, Funatsu T, Tsunoda M (2012a) Rapid determination of amino acids in biological samples using a monolithic silica column. Amino Acids 42(5):1897-902 CrossRef
33. Song Y, Funatsu T, Tsunoda M (2012b) Amino acid analysis using core–shell particle column. J Chromotogr B. doi:10.1016/j.jchromb.2012.09.005
34. Sugiura M, Kisumi M, Chibata I (1981) Biosynthetic pathway of beta-methylnorleucine, an antimetabolite produced by / Serratia marcescens. J Antibiot 34:1283-289
35. Sunasara KM, Cramer SM, Hauer CR, Rupp RG, Shoup VA (1999) Characterization of recombinant human brain-derived neurotrophic factor variants. Arch Biochem Biophys 372(2):248-60 CrossRef
36. Sycheva EV, Yampol’skaya TA, Preobrajenskaya ES, Novikova AE, Matrosov NG, Stoynova NV (2007) Overproduction of noncanonical amino acids by / Escherichia coli cells. Mikrobiologiya 76(6):805-12
37. Tsai LB, Lu HS, Kenney WC, Curless CC, Klein ML, Lai PH, Fenton DM, Altrock BW, Mann MB (1988) Control of misincorporation of de novo synthesized norleucine into recombinant interleukin-2 in / E. coli. Biochem Biophys Res Commun 156:733-39
38. Wan H, Blomberg LG (2000) Chiral separation of amino acids and peptides by capillary electrophoresis. J Chromatogr A 875(1-):43-8
39. Waterval WAH, Scheijen J, Ortmans-Ploemen M, Habets-van der Poel CD, Bierau J (2009) Quantitative UPLC-MS/MS analysis of underivatised amino acids in body fluids is a reliable tool for the diagnosis and follow-up of patients with inborn errors of metabolism. Clin Chim Acta 407(1-):36-2 CrossRef
40. Wu N, Clausen AM (2007) Fundamental and practical aspects of ultrahigh pressure liquid chromatography for fast separations. J Sep Sci 30(8):1167-182 CrossRef - 作者单位：Michael Biermann (1)
Bettina Bardl (1)
Sebastian Vollst?dt (1)
Julia Linnemann (1)
Uwe Knüpfer (1)
Guido Seidel (2)
Uwe Horn (1)
1. Leibniz-Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstrasse 11a, 07745, Jena, Germany
2. Wacker Biotech GmbH, Hans-Kn?ll Strasse 3, 07745, Jena, Germany - ISSN：1438-2199
文摘
In this study, a precise and reliable ultra-high performance liquid chromatography (UHPLC) method for the simultaneous determination of non-canonical (norvaline and norleucine) and standard amino acids (aspartic acid, glutamic acid, serine, histidine, glycine, threonine, arginine, tyrosine, methionine, valine, phenylalanine, isoleucine, leucine) in biopharmaceutical-related fermentation processes was established. After pre-column derivatization with ortho-phthaldialdehyde and 2-mercaptoethanol, the derivatives were separated on a sub-2?μm particle C18 reverse-phase column. Identification and quantification of amino acids were carried out by fluorescence detection. To test method feasibility on standard HPLC instruments, the assay was properly transferred to a core–shell particle C18 reverse-phase column. The limits of detection showed excellent sensitivity by values from 0.06 to 0.17?pmol per injection and limits of quantification between 0.19 and 0.89?pmol. In the present study, the newly established UHPLC method was applied to a recombinant antibody Escherichia coli fermentation process for the analysis of total free amino acids. We were able to specifically detect and quantify the unfavorable amino acids in such complex samples. Since we observed trace amounts of norvaline and norleucine during all fermentation phases, an obligatory process monitoring should be considered to improve quality of recombinant protein drugs in future.