Sortase-mediated ligations for the site-specific modification of proteins

Current Opinion in Chemical Biology

Volumn 22, Issue , 2014, Pages 122-128

  Schmohl, Lena ^a   Schwarzer, Dirk ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEIN; SORTASE; SORTASE A; UNCLASSIFIED DRUG; AMINOACYLTRANSFERASE; BACTERIAL PROTEIN; CYSTEINE PROTEINASE;

ARTICLE; BIOCHEMISTRY; CHEMICAL ANALYSIS; CHEMOSELECTIVE LIGATION; MOLECULAR BIOLOGY; NONHUMAN; PROTEIN ENGINEERING; PROTEIN MODIFICATION; SORTASE MEDIATED LIGATION; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES; AMINO ACID SEQUENCE; ANIMAL; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; PROCEDURES;

AMINO ACID SEQUENCE; AMINOACYLTRANSFERASES; ANIMALS; BACTERIA; BACTERIAL PROTEINS; CYSTEINE ENDOPEPTIDASES; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN ENGINEERING; PROTEINS;

EID: 84907818379     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2014.09.020     Document Type: Review

References (49)

1. Popp M.W., Antos J.M., Grotenbreg G.M., Spooner E., Ploegh H.L. Sortagging: a versatile method for protein labeling. Nat Chem Biol 2007, 3:707-708.
2. Kruger R.G., Otvos B., Frankel B.A., Bentley M., Dostal P., McCafferty D.G. Analysis of the substrate specificity of the Staphylococcus aureus sortase transpeptidase SrtA. Biochemistry 2004, 43:1541-1551.
3. Schneewind O., Fowler A., Faull K.F. Structure of the cell-wall anchor of surface-proteins in Staphylococcus aureus. Science 1995, 268:103-106.
4. Spirig T., Weiner E.M., Clubb R.T. Sortase enzymes in Gram-positive bacteria. Mol Microbiol 2011, 82:1044-1059.
5. Maresso A.W., Schneewind O. Sortase as a target of anti-infective therapy. Pharmacol Rev 2008, 60:128-141.
6. Mazmanian S.K., Ton-That H., Su K., Schneewind O. An iron-regulated sortase anchors a class of surface protein during Staphylococcus aureus pathogenesis. Proc Natl Acad Sci U S A 2002, 99:2293-2298.
7. Maresso A.W., Chapa T.J., Schneewind O. Surface protein IsdC and sortase B are required for heme-iron scavenging of Bacillus anthracis. J Bacteriol 2006, 188:8145-8152.
8. Ton-That H., Liu G., Mazmanian S.K., Faull K.F., Schneewind O. Purification and characterization of sortase, the transpeptidase that cleaves surface proteins of Staphylococcus aureus at the LPXTG motif. Proc Natl Acad Sci U S A 1999, 96:12424-12429.
9. Bentley M.L., Gaweska H., Kielec J.M., McCafferty D.G. Engineering the substrate specificity of Staphylococcurs aureus sortase A-the beta 6/beta 7 loop from SrtB confers NPQTN recognition to SrtA. J Biol Chem 2007, 282:6571-6581.
10. Weiner E.M., Robson S., Marohn M., Clubb R.T. The sortase A enzyme that attaches proteins to the cell wall of Bacillus anthracis contains an unusual active site architecture. J Biol Chem 2010, 285:23431-23441.
11. Race P.R., Bentley M.L., Melvin J.A., Crow A., Hughes R.K., Smith W.D., Sessions R.B., Kehoe M.A., McCafferty D.G., Banfield M.J. Crystal structure of Streptococcus pyogenes sortase A: impications for sortase mechanism. J Biol Chem 2009, 284:6924-6933.
12. Frankel B.A., Tong Y., Bentley M.L., Fitzgerald M.C., McCafferty D.G. Mutational analysis of active site residues in the Staphylococcus aureus transpeptidase SrtA. Biochemistry 2007, 46:7269-7278.
13. Clancy K.W., Melvin J.A., McCafferty D.G. Sortase transpeptidases insights into mechanism, substrate specificity, and inhibition. Biopolymers 2010, 94:385-396.
14. Frankel B.A., Kruger R.G., Robinson D.E., Kelleher N.L., McCafferty D.G. Staphylococcus aureus sortase transpeptidase SrtA: insight into the kinetic mechanism and evidence for a reverse protonation catalytic mechanism. Biochemistry 2005, 44:11188-11200.
15. Suree N., Yi S.W., Thieu W., Marohn M., Damoiseaux R., Chan A., Jung M.E., Clubb R.T. Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors. Bioorg Med Chem 2009, 17:7174-7185.
16. Popp M.W.L., Ploegh H.L. Making and breaking peptide bonds: protein engineering using sortase. Angew Chem Int Ed 2011, 50:5024-5032.
17. Mao H.Y., Hart S.A., Schink A., Pollok B.A. Sortase-mediated protein ligation: a new method for protein engineering. J Am Chem Soc 2004, 126:2670-2671.
18. Hess G.T., Cragnolini J.J., Popp M.W., Allen M.A., Dougan S.K., Spooner E., Ploegh H.L., Belcher A.M., Guimaraes C.P. M13 bacteriophage display framework that allows sortase-mediated modification of surface-accessible phage proteins. Bioconjug Chem 2012, 23:1478-1487.
19. Swee L.K., Guimaraes C.P., Sehrawat S., Spooner E., Barrasa M.I., Ploegh H.L. Sortase-mediated modification of alphaDEC205 affords optimization of antigen presentation and immunization against a set of viral epitopes. Proc Natl Acad Sci U S A 2013, 110:1428-1433.
20. Paterson B.M., Alt K., Jeffery C.M., Price R.I., Jagdale S., Rigby S., Williams C.C., Peter K., Hagemeyer C.E., Donnelly P.S. Enzyme-mediated site-specific bioconjugation of metal complexes to proteins: sortase-mediated coupling of copper-64 to a single-chain antibody. Angew Chem Int Ed 2014, 53:6115-6119.
21. Sakamoto T., Sawamoto S., Tanaka T., Fukuda H., Kondo A. Enzyme-mediated site-specific antibody-protein modification using a ZZ domain as a linker. Bioconjug Chem 2010, 21:2227-2233.
22. Mohlmann S., Mahlert C., Greven S., Scholz P., Harrenga A. In vitro sortagging of an antibody fab fragment: overcoming unproductive reactions of sortase with water and lysine side chains. ChemBioChem 2011, 12:1774-1780.
23. Popp M.W., Dougan S.K., Chuang T.Y., Spooner E., Ploegh H.L. Sortase-catalyzed transformations that improve the properties of cytokines. Proc Natl Acad Sci U S A 2011, 108:3169-3174.
24. Wu Z., Guo X., Guo Z. Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides. Chem Commun (Camb) 2011, 47:9218-9220.
25. Zhang J., Yamaguchi S., Hirakawa H., Nagamune T. Intracellular protein cyclization catalyzed by exogenously transduced Streptococcus pyogenes sortase A. J Biosci Bioeng 2013, 116:298-301.
26. Chan L., Cross H.F., She J.K., Cavalli G., Martins H.F., Neylon C. Covalent attachment of proteins to solid supports and surfaces via sortase-mediated ligation. PLoS ONE 2007, 2:e1164.
27. Sinisi A., Popp M.W., Antos J.M., Pansegrau W., Savino S., Nissum M., Rappuoli R., Ploegh H.L., Buti L. Development of an influenza virus protein array using Sortagging technology. Bioconjug Chem 2012, 23:1119-1126.
28. Steinhagen M., Zunker K., Nordsieck K., Beck-Sickinger A.G. Large scale modification of biomolecules using immobilized sortase A from Staphylococcus aureus. Bioorg Med Chem 2013, 21:3504-3510.
29. 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.
30. Jiang R., Wang L., Weingart J., Sun X.L. Chemoenzymatic bio-orthogonal chemistry for site-specific double modification of recombinant thrombomodulin. ChemBioChem 2014, 15:42-46.
31. Ling J.J.J., Policarpo R.L., Rabideau A.E., Liao X.L., Pentelute B.L. Protein thioester synthesis enabled by sortase. J Am Chem Soc 2012, 134:10749-10752.
32. Warden-Rothman R., Caturegli I., Popik V., Tsourkas A. Sortase-tag expressed protein ligation: combining protein purification and site-specific bioconjugation into a single step. Anal Chem 2013, 85:11090-11097.
33. Schmohl L., Schwarzer D. Chemo-enzymatic three-fragment assembly of semisynthetic proteins. J Pept Sci 2014, 20:145-151.
34. Ritzefeld M. Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry 2014, (Epub ahead of print).
35. Tsukiji S., Nagamune T. Sortase-mediated ligation a gift from Gram-positive bacteria to protein engineering. ChemBioChem 2009, 10:787-798.
36. Hackenberger C.P.R., Schwarzer D. Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed 2008, 47:10030-10074.
37. Kent S.B. Total chemical synthesis of proteins. Chem Soc Rev 2009, 38:338-351.
38. Mootz H.D. Split inteins as versatile tools for protein semisynthesis. ChemBioChem 2009, 10:2579-2589.
39. Antos J.M., Chew G.L., Guimaraes C.P., Yoder N.C., Grotenbreg G.M., Popp M.W.L., Ploegh H.L. Site-specific N- and C-terminal labeling of a single polypeptide using sortases of different specificity. J Am Chem Soc 2009, 131:10800-10801.
40. Pritz S., Wolf Y., Kraetke O., Klose J., Bienert M., Beyermann M. Synthesis of biologically active peptide nucleic acid-peptide conjugates by sortase-mediated ligation. J Org Chem 2007, 72:3909-3912.
41. Yamamura Y., Hirakawa H., Yamaguchi S., Nagamune T. Enhancement of sortase A-mediated protein ligation by inducing a beta-hairpin structure around the ligation site. Chem Commun 2011, 47:4742-4744.
42. Williamson D.J., Fascione M.A., Webb M.E., Turnbull W.B. Efficient N-terminal labeling of proteins by use of sortase. Angew Chem Int Ed 2012, 51:9377-9380.
43. Liu F., Luo E.Y., Flora D.B., Mezo A.R. Irreversible sortase A-mediated ligation driven by diketopiperazine formation. J Org Chem 2014, 79:487-492.
44. Li Y.M., Li Y.T., Pan M., Kong X.Q., Huang Y.C., Hong Z.Y., Liu L. Irreversible site-specific hydrazinolysis of proteins by use of sortase. Angew Chem Int Ed 2014, 53:2198-2202.
45. Strijbis K., Spooner E., Ploegh H.L. Protein ligation in living cells using sortase. Traffic 2012, 13:780-789.
46. 2+-independent Staphylococcus aureus sortase A mutants. Biotechnol Bioeng 2012, 109:2955-2961.
47. 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.
48. Chen I., Dorr B.M., Liu D.R. A general strategy for the evolution of bond-forming enzymes using yeast display. Proc Natl Acad Sci U S A 2011, 108:11399-11404.
49. Deng F.K., Zhang L., Wang Y.T., Schneewind O., Kent S.B.H. Total chemical synthesis of the enzyme sortase A DN59 with full catalytic activity. Angew Chem Int Ed 2014, 53:4662-4666.