Scalable purification of the lantibiotic nisin and isolation of chemical/enzymatic cleavage fragments suitable for semi-synthesis

Journal of Peptide Science

Volumn 19, Issue 11, 2013, Pages 692-699

  Slootweg, Jack C ^a   Liskamp, Rob M J ^a,b   Rijkers, Dirk T S ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Antimicrobial peptides; CNBr cleavage; Enzymatic digestion; LC MS; Nisin; Peptide purification; Semi synthesis

Indexed keywords

ASPARTIC ACID; CHYMOTRYPSIN; LYSINE; METHIONINE; NISIN; TRYPSIN;

AMINO ACID SEQUENCE; ARTICLE; DRUG MECHANISM; DRUG PURIFICATION; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; EXTRACTION; FOLLOW UP; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRECIPITATION; PRIORITY JOURNAL; PROTEIN CLEAVAGE; SYNTHESIS;

ANTIMICROBIAL PEPTIDES; CNBR CLEAVAGE; ENZYMATIC DIGESTION; LC-MS; NISIN; PEPTIDE PURIFICATION; SEMI-SYNTHESIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHYMOTRYPSIN; CYANOGEN BROMIDE; MOLECULAR SEQUENCE DATA; NISIN; PEPTIDE FRAGMENTS; PROTEOLYSIS; TRYPSIN;

EID: 84885942732     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2551     Document Type: Article

References (38)

1. Chatterjee C, Paul M, Xie L, van der Donk WA. Biosynthesis and mode of action of lantibiotic. Chem. Rev. 2000; 105: 633-684.
2. Willey JM, van der Donk WA. Lantibiotics: peptides of diverse structure and function. Annu. Rev. Microbiol. 2007; 61: 477-501.
3. Knerr PJ, van der Donk WA. Discovery, biosynthesis, and engineering of lantipeptides. Annu. Rev. Biochem. 2012; 81: 479-505.
4. Breukink E, de Kruijff B. Lipid II as a target for antibiotics. Nat. Rev. Drug Discovery 2006; 5: 321-332.
5. Hsu ST, Breukink E, Tischenko E, Lutters MAG, de Kruijff B, Kaptein R, Bonvin AMJJ, van Nuland NAJ. The nisin-lipid II complex reveals a pyrophosphate cage that provides a blueprint for novel antibiotics. Nat. Struct. Mol. Biol. 2004; 11: 963-967.
6. Hasper HE, Kramer NE, Smith JL, Hillman JD, Zachariah C, Kuipers OP, de Kruijff B, Breukink E. An alternative bactericidal mechanism of action for lantibiotic peptides that target lipid II. Science 2006; 313: 1636-1637.
7. Hsu ST, Breukink E, de Kruijff B, Kaptein R, Bonvin AMJJ, van Nuland NAJ. Mapping the targeted membrane pore formation mechanism by solution NMR: the nisin Z and lipid II interaction in SDS micelles. Biochemistry 2002; 41: 7670-7676.
8. Breukink E, van Kraaij C, Demel R, Siezen RJ, Kuipers OP, de Kruijff B. The C-terminal region of nisin is responsible for the initial interaction of nisin with the target membrane. Biochemistry 1997; 36: 6968-6976.
9. van Kraaij C, Breukink E, Noordermeer M, Demel R, Siezen RJ, Kuipers OP, de Kruijff B. Pore formation by nisin involves translocation of its C-terminal part across the membrane. Biochemistry 1998; 37: 16033-16040.
10. Breukink E, Wiedemann I, van Kraaij C, Kuipers OP, Sahl HG, de Kruijff B. Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic. Science 1999; 286: 2361-2364.
11. Wiedemann I, Breukink E, van Kraaij C, Kuipers OP, Bierbaum G, de Kruijff B, Sahl HG. Specific binding of nisin to the peptidoglycan precursor lipid II combines pore formation and inhibition of cell wall biosynthesis for potent antibiotic activity. J. Biol. Chem. 2001; 276: 1772-1779.
12. Breukink E, van Heusden HE, Vollmerhaus PJ, Swiezewska E, Brunner L, Walker S, Heck AJR, de Kruijff B. Lipid II is an intrinsic component of the pore induced by nisin in bacterial membranes. J. Biol. Chem. 2003; 278: 19898-19903.
13. Hasper HE, de Kruijff B, Breukink E. Assembly and stability of nisin-lipid II pores. Biochemistry 2004; 43: 11567-11575.
14. van Kraaij C, de Vos WM, Siezen RJ, Kuipers OP. Lantibiotics: biosynthesis, mode of action and applications. Nat. Prod. Res. 1999; 16: 575-587.
15. Ghalit N, Rijkers DTS, Kemmink J, Versluis C, Liskamp RMJ. Pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis. Chem. Commun. 2005; 192-194.
16. Ghalit N, Rijkers DTS, Liskamp RMJ. Alkene- and alkyne-bridged mimics of nisin as potential peptide-based antibiotics. J. Mol. Catal. A, Chem. 2006; 254: 68-77.
17. Ghalit N, Kemmink J, Hilbers HW, Versluis C, Rijkers DTS, Liskamp RMJ. Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis. Org. Biomol. Chem. 2007; 5: 924-934.
18. Ghalit N, Reichwein JF, Hilbers HW, Breukink E, Rijkers DTS, Liskamp RMJ, Synthesis of bicyclic alkene-/alkane-bridged nisin mimics by ring-closing metathesis and their biochemical evaluation as lipid II binders: toward the design of potential novel antibiotics. ChemBioChem 2007; 8: 1540-54.
19. Slootweg JC, Rijkers DTS, Liskamp RMJ. Synthesis, structural characterization and application of crossed alkene-bridged nisin DE-ring mimics for semi-synthesis of nisin hybrid mimics. J. Pept. Sci. 2012; 18(Supplement S1): S127-S128.
20. Cheigh CI, Kook MC, Kim SB, Hong YH, Pyun YR. Simple one-step purification of nisin Z from unclarified culture broth of Lactococcus lactis subsp. lactis A164 using expanded bed ion exchange chromatography. Biotechnol. Lett. 2004; 26: 1341-1345.
21. Taylor TM, Davidson PM, Zhong Q. Extraction of nisin from a 2.5% commercial nisin product using methanol and ethanol solutions. J. Food Protect. 2007; 70: 1272-1276.
22. Jozala AF, Lopes AM, Mazzola PG, Magalhães PO, Vessoni Penna TC, Pessoa Jr A. Liquid-liquid extraction of commercial and biosynthesized nisin by aqueous two-phase micellar systems. Enzym. Microb. Tech. 2008; 42: 107-112.
23. Abts A, Mavaro A, Stindt J, Bakkes PJ, Metzger S, Driessen AJM, Smits SHJ, Schmitt L. Easy and rapid purification of highly active nisin. Int. J. Peptides 2011; 175145.
24. Burianek LL, Yousef AE. Solvent extraction of bacteriocins from liquid cultures. Lett. Appl. Microbiol. 2000; 31: 193-197.
25. URL: http://www.chr-hansen.com/products/product-areas/enzymes/our-products/bioprotective-enzymes/chrisinr.html [last accessed on May 14, 2013]
26. URL: http://www.sigmaaldrich.com/catalog/product/sigma/n5764?lang=en®ion=NL [last accessed on May 14, 2013]
27. Chan WC, Leyland M, Clark J, Dodd HM, Lian LY, Gasson MJ, Bycroft BW, Roberts GC. Structure-activity relationships in the peptide antibiotic nisin: antibacterial activity of fragments of nisin. FEBS Lett. 1996; 390: 129-132.
28. Fukase K, Kitazawa M, Sano A, Shimbo K, Fujita H, Horimoto S, Wakamiya T, Shiba T. Total synthesis of peptide antibiotic nisin. Tetrahedron Lett. 1988; 29: 795-798.
29. Bregant S, Tabor AB. Orthogonally protected lanthionines: synthesis and use for the solid-phase synthesis of an analogue of nisin ring C. J. Org. Chem. 2005; 70: 2430-2438.
30. Mothia B, Appleyard AN, Wadman S, Tabor AB. Synthesis of peptides containing overlapping lanthionine bridges on the solid phase: an analogue of rings D and E of the lantibiotic nisin. Org. Lett. 2011; 13: 4216-4219.
31. Gross E, Morell JL. Nisin. The assignment of sulfide bridges of β-methyllanthionine to a novel bicyclic structure of identical ring size. J. Am. Chem. Soc. 1970; 92: 2919-2920.
32. Liu W, Hansen JN. Some chemical and physical properties of nisin, a small-protein antibiotic produced by Lactococcus lactis. Appl. Environ. Microbiol. 1990; 56: 2551-2558.
33. Gross E. The cyanogen bromide reaction. Methods Enzymol. 1976; 11: 238-255.
34. Goodlett DR, Armstrong FB, Creech RJ, van Breemen RB. Formylated peptides from cyanogen bromide digests identified by fast atom bombardment mass spectrometry. Anal. Biochem. 1990; 186: 116-120.
35. Freidinger RM, Schwenk Perlow D, Veber DF. Protected lactam-bridged dipeptides for use as conformational constraints in peptides. J. Org. Chem. 1982; 47: 104-109.
36. Kaiser R, Metzka L. Enhancement of cyanogen bromide cleavage yields for methionyl-serine and methionyl-threonine peptide bonds. Anal. Biochem. 1999; 266: 1-8.
37. Tabor AB. The challenge of the lantibiotics: synthetic approaches to thioether-bridged peptides. Org. Biomol. Chem. 2011; 9: 7606-7628.
38. Arnusch CJ, Bonvin AMJJ, Verel AM, Jansen WTM, Liskamp RMJ, de Kruijff B, Pieters RJ, Breukink E. The vancomycin-nisin(1-12) hybrid restores activity against vancomycin resistant Enterococci. Biochemistry 2008; 47: 12661-12663.