Chemo-enzymatic three-fragment assembly of semisynthetic proteins

Journal of Peptide Science

Volumn 20, Issue 2, 2014, Pages 145-151

  Schmohl, Lena ^a   Schwarzer, Dirk ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

FRET reporter; phosphopantetheine transferase; protein semisynthesis; sortase mediated ligation

Indexed keywords

GLUTATHIONE TRANSFERASE; HISTONE H3; PANTETHEINE PHOSPHATE; SORTASE; SYNTHETIC PEPTIDE; AMINOACYLTRANSFERASE; BACTERIAL PROTEIN; CYSTEINE PROTEINASE; PEPTIDE FRAGMENT; PROTEIN; SORTASE A;

AMINO TERMINAL SEQUENCE; ARTICLE; CONJUGATION; CONTROLLED STUDY; ENZYME MECHANISM; FLUORESCENCE RESONANCE ENERGY TRANSFER; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN PURIFICATION; PROTEIN SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; SYNTHESIS;

AMINOACYLTRANSFERASES; BACTERIAL PROTEINS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYSTEINE ENDOPEPTIDASES; MOLECULAR STRUCTURE; PEPTIDE FRAGMENTS; PROTEINS;

EID: 84892802193     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2600     Document Type: Article

References (29)

1. Hackenberger CPR,;, Schwarzer D,. Chemoselective ligation and modification strategies for peptides and proteins. Angew. Chem. Int. Ed. 2008; 47: 10030-10074.
2. Kent SBH,. Total chemical synthesis of proteins. Chem. Soc. Rev. 2009; 38: 338-351.
3. Dawson PE, Muir TW, Clarklewis I, Kent SBH,. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779.
4. Muir TW, Sondhi D, Cole PA,. Expressed protein ligation: A general method for protein engineering. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 6705-6710.
5. Popp MWL, Ploegh HL,. Making and breaking peptide bonds: protein engineering using sortase. Angew. Chem. Int. Ed. 2011; 50: 5024-5032.
6. Tsukiji S, Nagamune T,. Sortase-mediated ligation: a gift from gram-positive bacteria to protein engineering. Chembiochem 2009; 10: 787-798.
7. Piotukh K, Geltinger B, Heinrich N, Gerth F, Beyermann M, Freund C, Schwarzer D,. Directed evolution of sortase a mutants with altered substrate selectivity profiles. J. Am. Chem. Soc. 2011; 133: 17536-17539.
8. Teschke T, Geltinger B, Dose A, Freund C, Schwarzer D,. Probing the recognition of post-translational modifications by combining sortase-mediated ligation and phage-assisted selection. Acs Chem. Biol. 2013; 8: 1692-1697.
9. Ton-That H, Marraffini LA, Schneewind O,. Protein sorting to the cell wall envelope of Gram-positive bacteria. Bba-Mol. Cell. Res. 2004; 1694: 269-278.
10. Clancy KW, Melvin JA, McCafferty DG,. Sortase transpeptidases: insights into mechanism, substrate specificity, and inhibition. Biopolymers 2010; 94: 385-396.
11. Bang D, Pentelute BL, Kent SBH,. Kinetically controlled ligation for the convergent chemical synthesis of proteins; Angew. Chem. Int. Ed. 2006; 45: 3985-3988.
12. Antos JM, Chew GL, Guimaraes CP, Yoder NC, Grotenbreg GM, Popp MWL, Ploegh HL,. Site-specific N- and C-terminal labeling of a single polypeptide using sortases of different specificity. J. Am. Chem. Soc. 2009; 131: 10800-10801.
13. Race PR, Bentley ML, Melvin JA, Crow A, Hughes RK, Smith WD, Sessions RB, Kehoe MA, McCafferty DG, Banfield MJ,. Crystal structure of streptococcus pyogenes sortase A: implications for sortase mechanism. J. Biol. Chem. 2009; 284: 6924-6933.
14. Lambalot RH, Gehring AM, Flugel RS, Zuber P, LaCelle M, Marahiel MA, Reid R, Khosla C, Walsh CT,. A new enzyme superfamily-the phosphopantetheinyl transferases. Chem. Biol. 1996; 3: 923-936.
15. Yin J, Liu F, Li XH, Walsh CT,. Labeling proteins with small molecules by site-specific posttranslational modification. J. Am. Chem. Soc. 2004; 126: 7754-7755.
16. Zou YK, Yin J,. Phosphopantetheinyl transferase catalyzed site-specific protein labeling with ADP conjugated chemical probes. J. Am. Chem. Soc. 2009; 131: 7548-7549.
17. George N, Pick H, Vogel H, Johnsson N, Johnsson K,. Specific labeling of cell surface proteins with chemically diverse compounds. J. Am. Chem. Soc. 2004; 126: 8896-8897.
18. Yin J, Straight PD, McLoughlin SM, Zhou Z, Lin AJ, Golan DE, Kelleher NL, Kolter R, Walsh CT,. Genetically encoded short peptide tag for versatile protein labeling by Sfp phosphopantetheinyl transferase. Proc. Natl. Acad. Sci. U.S.A. 2005; 102: 15815-15820.
19. Zhou Z, Cironi P, Lin AJ, Xu YQ, Hrvatin S, Golan DE, Silver PA, Walsh CT, Yin J,. Genetically encoded short peptide tags for orthogonal protein labeling by Sfp and AcpS phosphopantetheinyl transferases. Acs Chem. Biol. 2007; 2: 337-346.
20. Chen I, Dorr BM, Liu DR,. A general strategy for the evolution of bond-forming enzymes using yeast display. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 11399-11404.
21. Newman RH, Fosbrink MD, Zhang J,. Genetically encodable fluorescent biosensors for tracking signaling dynamics in living cells. Chem. Rev. 2011; 111: 3614-3666.
22. Yi L, Sun H, Itzen A, Triola G, Waldmann H, Goody RS, Wu YW,. One-pot dual-labeling of a protein by two chemoselective reactions. Angew. Chem. Int. Ed. 2011; 50: 8287-8290.
23. Lin CW, Ting AY,. A genetically encoded fluorescent reporter of histone phosphorylation in living cells. Angew. Chem. Int. Ed. 2004; 43: 2940-2943.
24. Lau OD, Kundu TK, Soccio RE, Ait-Si-Ali S, Khalil EM, Vassilev A, Wolffe AP, Nakatani Y, Roeder RG, Cole PA,. HATs off: selective synthetic inhibitors of the histone acetyltransferases p300 and PCAF. Mol. Cell 2000; 5: 589-595.
25. Matsumoto T, Tanaka T, Kondo A,. Sortase A-catalyzed site-specific coimmobilization on microparticles via streptavidin. Langmuir 2012; 28: 3553-3557.
26. Cerutti H, Casas-Mollano JA,. Histone H3 phosphorylation universal code or lineage specific dialects? Epigenetics 2009; 4: 71-75.
27. Wei Y, Yu LL, Bowen J, Gorovsky MA, Allis CD,. Phosphorylation of histone H3 is required for proper chromosome condensation and segregation. Cell 1999; 97: 99-109.
28. Liokatis S, Stutzer A, Elsasser SJ, Theillet FX, Klingberg R, van Rossum B, Schwarzer D, Allis CD, Fischle W, Selenko P,. Phosphorylation of histone H3 Ser10 establishes a hierarchy for subsequent intramolecular modification events. Nat. Struct. Mol. Biol. 2012; 19: 819-823.
29. Nakanishi M, Yatome C, Ishida N, Kitade Y,. Putative ACP phosphodiesterase gene (acpD) encodes an azoreductase. J. Biol. Chem. 2001; 276: 46394-46399.