Structural, dynamic, and chemical characterization of a novel S-glycosylated bacteriocin

Biochemistry

Volumn 50, Issue 14, 2011, Pages 2748-2755

  Venugopal, Hariprasad ^a   Edwards, Patrick J B ^a   Schwalbe, Martin ^a   Claridge, Jolyon K ^a   Libich, David S ^a   Stepper, Judith ^a   Loo, Trevor ^a   Patchett, Mark L ^a   Norris, Gillian E ^a   Pascal, Steven M ^a  

^a MASSEY UNIVERSITY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOCINS; BACTERIOSTATIC; C-TERMINAL TAIL; CHEMICAL CHARACTERIZATION; CONFORMATIONAL STABILITIES; DISULFIDE BONDS; GLYCOSYLATED; LACTOBACILLUS PLANTARUM; MODE OF ACTION; N-ACETYLGLUCOSAMINE; NATURAL PRESERVATIVES; PEPTIDE CONFORMATION; POST-TRANSLATIONAL MODIFICATIONS; PROBIOTICS; SIDE CHAINS; SPECIFIC ACTIVITY;

AMINO ACIDS; CONFORMATIONS; COVALENT BONDS; MAGNETIC RESONANCE; OXYGEN; PEPTIDES; SULFUR;

SUGARS;

BACTERIOCIN; CYSTEINE; GLYCOCIN F; N ACETYLGLUCOSAMINE; OXYGEN; SERINE; SULFUR; UNCLASSIFIED DRUG;

ALPHA HELIX; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DISULFIDE BOND; LACTOBACILLUS PLANTARUM; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN PROCESSING;

ACETYLGLUCOSAMINE; BACTERIOCINS; CYSTEINE; DISULFIDES; GLYCOSYLATION; KINETICS; LACTOBACILLUS PLANTARUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXYGEN; PROTEIN CONFORMATION; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEIN STRUCTURE, SECONDARY; SERINE; SULFUR;

BACTERIA (MICROORGANISMS); LACTOBACILLUS PLANTARUM;

EID: 79953711158     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi200217u     Document Type: Article

References (31)

1. Löte, C. J. and Weiss, J. B. (1971) Identification of digalactosylcysteine in a glycopeptide isolated from urine by a new preparative technique FEBS Lett. 16, 81-85
2. Weiss, J. B., Löte, C. J., and Bobinski, H. (1971) New low molecular weight glycopeptide containing triglucosylcysteine in human erythrocyte membrane Nat. New Biol. 234, 25-26
3. Oman, T. J., Boettcher, J. M., Wang, H., Okalibe, X. N., and van der Donk, W. A. (2011) Sublancin is not a lantibiotic but an S- linked glycopeptide Nat. Chem. Biol. 7 (2) 78-80
4. Stepper, J., Shastri, S., Loo, T. S., Preston, J. C., Novak, P., Man, P., Moore, C. H., Havlíček, V., Patchett, M. L., and Norris, G. E. (2011) Cysteine S- glycosylation, a new post-translational modification found in glycopeptide bacteriocins FEBS Lett. 585, 645-650
5. Baran, E. and Drabarek, S. (1978) Pol. J. Chem. 52, 941-946
6. Jahn, M., Marles, J., Warren, R. A., and Withers, S. G. (2003) Thioglycoligases: Mutant Glycosidases for Thioglycoside Synthesis Angew. Chem., Int. Ed. 42, 352-354 (Pubitemid 36176322)
7. Driguez, H. (2001) Thiooligosaccharides as Tools for Structural Biology ChemBioChem 2, 311-318 (Pubitemid 33722572)
8. Cohen, S. B. and Halcomb, R. L. (2002) Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S- Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis J. Am. Chem. Soc. 124, 2534-2543 (Pubitemid 34251766)
9. Gerz, M., Matter, H., and Kessler, H. (1993) S- Glycosylated Cyclic Peptides Angew. Chem., Int. Ed. 32, 269-271
10. Galonić, D. P., van der Donk, W. A., and Gin, D. Y. (2004) Site-Selective Conjugation of Thiols with Aziridine-2-Carboxylic Acid-Containing Peptides J. Am. Chem. Soc. 126, 12712-12713 (Pubitemid 39372266)
11. Galonić, D. P., Ide, N. D., van der Donk, W. A., and Gin, D. Y. (2005) Aziridine-2-carboxylic Acid-Containing Peptides: Application to Solution- and Solid-Phase Convergent Site-Selective Peptide Modification J. Am. Chem. Soc. 127, 7359-7369 (Pubitemid 40746020)
12. Hili, R., Rai, V., and Yudin, A. K. (2010) Macrocyclization of Linear Peptides Enabled by Amphoteric Molecules J. Am. Chem. Soc. 132, 2889-2891
13. Gillor, O., Etzion, A., and Riley, M. A. (2008) The dual role of bacteriocins as anti- and probiotics Appl. Microbiol. Biotechnol. 81, 591-606
14. Corr, S. C., Li, Y., Riedel, C. U., O'Toole, P. W., Hill, C., and Gahan, C. G. (2007) Bacteriocin production as a mechanism for the antiinfective activity of Lactobacillus salivarius UCC118 Proc. Natl. Acad. Sci. U.S.A. 104, 7617-7621 (Pubitemid 47185955)
15. Klaenhammer, T. R. (1993) Genetics of bacteriocins produced by lactic acid bacteria FEMS Microbiol. Rev. 12, 39-85 (Pubitemid 23266726)
16. Cotter, P. D., Hill, C., and Ross, R. P. (2005) Bacteriocins: Developing innate immunity for food Nat. Rev. Microbiol. 3, 777-788 (Pubitemid 41518738)
17. 13C chemical-shift data J. Biomol. NMR 4, 171-180
18. Berjanskii, M. V. and Wishart, D. S. (2007) The RCI server: Rapid and accurate calculation of protein flexibility using chemical shifts Nucleic Acids Res. 35, W531-W537
19. CH J. Am. Chem. Soc. 127, 6154-6155 (Pubitemid 40627725)
20. Schanda, P., Kupce, E., and Brutscher, B. (2005) SOFAST-HMQC experiments for recording two-dimensional heteronuclear correlation spectra of proteins within a few seconds J. Biomol. NMR 33, 199-211 (Pubitemid 43118574)
21. Fregeau Gallagher, N. L., Sailer, M., Niemczura, W. P., Nakashima, T. T., Stiles, M. E., and Vederas, J. C. (1997) Three-dimensional structure of leucocin A in trifluoroethanol and dodecylphosphocholine micelles: Spatial location of residues critical for biological activity in type IIa bacteriocins from lactic acid bacteria Biochemistry 36, 15062-15072 (Pubitemid 27527970)
22. Uteng, M., Huge, H. H., Markwick, P. R., Fimland, G., Mantzilas, D., Nissen-Meyer, J., and Muhle-Goll, C. (2003) Three-dimensional structure in lipid micelles of the pediocin-like antimicrobial peptide sakacin P and a sakacin P variant that is structurally stabilized by an inserted C-terminal disulfide bridge Biochemistry 42, 11417-11426 (Pubitemid 37205735)
23. Haugen, H. S., Fimland, G., Nissen-Meyer, J., and Kristiansen, P. E. (2005) Three-dimensional structure in lipid micelles of the pediocin-like antimicrobial peptide curvacin A Biochemistry 44, 16149-16157 (Pubitemid 41785813)
24. Vranken, W. F., Boucher, W., Stevens, T. J., Fogh, R. H., Pajon, A., Llinas, M., Ulrich, E. L., Markley, J. L., Ionides, J., and Laue, E. D. (2005) The CCPN data model for NMR spectroscopy: Development of a software pipeline Proteins 59, 687-696 (Pubitemid 40695845)
25. Marion, D., Kay, L. E., Sparks, S. W., Torchia, D. A., and Bax, A. (1989) Three-dimensional heteronuclear NMR of nitrogen-15 labeled proteins J. Am. Chem. Soc. 111, 1515-1517
26. Fesik, S. W. and Zuiderweg, E. R. (1990) Heteronuclear three-dimensional NMR spectroscopy of isotopically labelled biological macromolecules Q. Rev. Biophys. 23, 97-131
27. Bax, A. and Grzesiek, S. (1993) Methodological advances in protein NMR Acc. Chem. Res. 26, 131-138
28. 15N) NMR assignments and secondary structure of the basic region-helix-loop-helix domain of E47 Protein Sci. 6, 175-184 (Pubitemid 27045257)
29. Habeck, M., Rieping, W., Linge, J. P., and Nilges, M. (2004) NOE assignment with ARIA 2.0: The nuts and bolts Methods Mol. Biol. 278, 379-402
30. DeLano, W. L. (2008) The PyMOL Molecular Graphics System, DeLano Scientific LLC, Palo Alto, CA.
31. Laskowski, R. A., Rullmannn, J. A., MacArthur, M. W., Kaptein, R., and Thornton, J. M. (1996) AQUA and PROCHECK-NMR: Programs for checking the quality of protein structures solved by NMR J. Biomol. NMR 8 (4) 477-486 (Pubitemid 126706801)