Engineering an affinity tag for genetically encoded cyclic peptides

Biotechnology and Bioengineering

Volumn 92, Issue 7, 2005, Pages 820-830

  Naumann, Todd A ^a   Savinov, Sergey N ^a   Benkovic, Stephen J ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Cyclic peptide; Genetic selection; Intein

Indexed keywords

AMINO ACIDS; CELLS; GENES; PURIFICATION;

CYCLIC PEPTIDE; GENETIC SELECTION; INTEIN;

PROTEINS;

CYCLOPEPTIDE; INTEIN; PEPTIDE LIBRARY; STREPTAVIDIN;

ARTICLE; CELL FUNCTION; GENETIC ENGINEERING; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN EXPRESSION; PROTEIN MOTIF; PROTEIN PURIFICATION; CHEMISTRY; GENETICS; METABOLISM; PROTEIN ENGINEERING;

AMINO ACID MOTIFS; INTEINS; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; PROTEIN BINDING; PROTEIN ENGINEERING; STREPTAVIDIN;

EID: 33644831071     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.20644     Document Type: Article

References (42)

1. Abel-Santos E, Scott CP, Benkovic SJ. 2003. Use of inteins for the in vivo production of stable cyclic peptide libraries in E. coli. Methods Mol Biol 205:281-294.
2. Bayer EA, Ben-Hur H, Wilchek M. 1990. Isolation and properties of streptavidin. Methods Enzymol 184:80-89.
3. Caponigro G, Abedi MR, Hurlburt AP, Maxfield A, Judd W, Kamb A. 1998. Transdominant genetic analysis of a growth control pathway. Proc Natl Acad Sci USA 95:7508-7513.
4. Chong S, Mersha FB, Comb DG, Scott ME, Landry D, Vence LM, Perler FB, Benner J, Kucera RB, Hirvonen CA, Pelletier JJ, Paulus H, Xu MQ. 1997. Single-column purification of free recombinant proteins using a self-cleavable affinity tag derived from a protein splicing element. Gene 192:271-281.
5. Devlin JJ, Panganiban LC, Devlin PE. 1990. Random peptide libraries: A source of specific protein binding molecules. Science 249:404-406.
6. Ding Y, Xu MQ, Ghosh I, Chen X, Ferrandon S, Lesage G, Rao Z. 2003. Crystal structure of a mini-intein reveals a conserved catalytic module involved in side chain cyclization of asparagine during protein splicing. J Biol Chem 278:39133-39142.
7. Ellman GL. 1959. Tissue sulfhydryl groups. Arch Biochem Biophys 82:70-77.
8. Evans TCJRTC, Xu MQ. 2002. Mechanistic and kinetic considerations of protein splicing. Chem Rev 102:4869-4884.
9. Geyer CR, Colman-Lerner A, Brent R. 1999. "Mutagenesis" by peptide aptamers identifies genetic network members and pathway connections. Proc Natl Acad Sci USA 96:8567-8572.
10. Giebel LB, Cass RT, Milligan DL, Young DC, Arze R, Johnson CR. 1995. Screening of cyclic peptide phage libraries identifies ligands that bind streptavidin with high affinities. Biochemistry 34:15430-15435.
11. Green NM. 1965. A spectophotometric assay for avidin and biotin based on binding of dyes by avidin. Biochem J 94:23C-24C.
12. Green N. 1975. Avidin. In: Anfinsen C, Edsall J, Richards F, editors. Advances in protein chemistry, Vol. 29. New York: Academic Press. pp 85-133.
13. Green NM. 1990. Avidin and streptavidin. Methods Enzymol 184:51-67.
14. Guzman LM, Belin D, Carson MJ, Beckwith J. 1995. Tight regulation, modulation, and high-level expression by vectors containing the arabinose PBAD promoter. J Bacteriol 177:4121-4130.
15. Horswill AR, Savinov SN, Benkovic SJ. 2004. A systematic method for identifying small-molecule modulators of protein-protein interactions. Proc Natl Acad Sci USA 101:15591-15596.
16. Houghten RA, Pinilla C, Blondelle SE, Appel JR, Dooley CT, Cuervo JH. 1991. Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery. Nature 354:84-86.
17. Kamb A, Caponigro G. 2001. Peptide inhibitors expressed in vivo. Curr Opin Chem Biol 5:74-77.
18. Kamb A, Teng DH. 2000. Transdominant genetics, peptide inhibitors and drug targets. Curr Opin Mol Ther 2:662-669.
19. Katz BA. 1995. Binding to protein targets of peptidic leads discovered by phage display: Crystal structures of streptavidin-bound linear and cyclic peptide ligands containing the HPQ sequence. Biochemistry 34:15421-15429.
20. Kee KS, Jois SD. 2003. Design of beta-turn based therapeutic agents. Curr Pharm Des 9:1209-1224.
21. Khlebnikov A, Datsenko KA, Skaug T, Wanner BL, Keasling JD. 2001. Homogeneous expression of the P(BAD) promoter in Escherichia coli by constitutive expression of the low-affinity high-capacity AraE transporter. Microbiology 147:3241-3247.
22. Kinsella TM, Ohashi CT, Harder AG, Yam GC, Li W, Peelle B, Pali ES, Bennett MK, Molineaux SM, Anderson DA, Masuda ES, Payan DG. 2002. Retrovirally delivered random cyclic peptide libraries yield inhibitors of interleukin-4 signaling in human B cells. J Biol Chem 277:37512-37518.
23. Kirley TL. 1989. Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Anal Biochem 180:231-236.
24. Ladner RC. 1995. Constrained peptides as binding entities. Trends Biotechnol 13:426-430.
25. Ladner RC, Sato AK, Gorzelany J, de Souza M. 2004. Phage display-derived peptides as therapeutic alternatives to antibodies. Drug Discov Today 9:525-529.
26. Latham PW. 1999. Therapeutic peptides revisited. Nat Biotechnol 17:755-757.
27. McBride JD, Freeman N, Domingo GJ, Leatherbarrow RJ. 1996. Selection of chymotrypsin inhibitors from a conformationally-constrained combinatorial peptide library. J Mol Biol 259:819-827.
28. McConnell SJ, Kendall ML, Reilly TM, Hoess RH. 1994. Constrained peptide libraries as a tool for finding mimotopes. Gene 151:115-158.
29. Needleman SB, Wunsch CD. 1970. A general method applicable to the search for similarities in the amino acid sequence of two proteins. J Mol Biol 48:443-453.
30. Norman TC, Smith DL, Sorger PK, Drees BL, O'Rourke SM, Hughes TR, Roberts CJ, Friend SH, Fields S, Murray AW. 1999. Genetic selection of peptide inhibitors of biological pathways. Science 285:591-595.
31. Perler FB. 2002. In Base: the Intein Database. Nucleic Acids Res 30:383-384.
32. Rose GD, Gierasch LM, Smith JA. 1985. Turns in peptides and proteins. Adv Protein Chem 37:1-109.
33. Schmidt TG, Skerra A. 1994. One-step affinity purification of bacterially produced proteins by means of the "Strep tag" and immobilized recombinant core streptavidin. J Chromatogr A 676:337-345.
34. Schogger H, von Jagow G. 1987. Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal Biochem 166:368-379.
35. Scott CP, Abel-Santos E, Wall M, Wahnon DC, Benkovic SJ. 1999. Production of cyclic peptides and proteins in vivo. Proc Natl Acad Sci USA 96:13638-13643.
36. Scott CP, Abel-Santos E, Jones AD, Benkovic SJ. 2001. Structural requirements for the biosynthesis of backbone cyclic peptide libraries. Chem Biol 8:801-815.
37. Shindler JS, Childs RE, Bardsley WG. 1976. Peroxidase from human cervical mucus. The isolation and characterization. Eur J Biochem 65:325-331.
38. Srinivas NR, Mamidi RN. 2003. Bioanalytical considerations for compounds containing free sulfhydryl groups. Biomed Chromatogr 17:285-291.
39. Tan DS, Foley MA, Shair MD, Shreiber SL. 1998. Stereoselective synthesis of over two million compounds having structural features both reminiscent of natural products and compatible with miniaturized cell-based assays. J Am Chem Soc 120:8565-8566.
40. Terpe K. 2003. Overview of tag protein fusions: from molecular and biochemical fundamentals to commercial systems. Appl Microbiol Biotechnol 60:523-533.
41. Veber DF, Freidlinger RM, Perlow DS, Paleveda WJ, Jr., Holly FW, Strachan RG, Nutt RF, Arison BH, Homnick C, Randall WC, Glitzer MS, Saperstein R, Hirschmann R. 1981. A potent cyclic hexapeptide analogue of somatostatin. Nature 292:55-58.
42. Wu H, Xu MQ, Liu XQ. 1998. Protein trans-splicing and functional mini-inteins of a cyanobacterial dnaB intein. Biochim Biophys Acta 1387:422-432.