Sortagging: a robust and efficient chemoenzymatic ligation strategy

Ritzefeld M (2014)
Chemistry (Weinheim an der Bergstrasse, Germany) 20(28): 8516-8529.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Ritzefeld, MarkusUniBi
Einrichtung
Fakultät für Chemie > Organische Chemie III
Abstract / Bemerkung
Bioorthogonal, chemoselective ligation methods are an essential part of the tools utilized to investigate biochemical pathways. Specifically enzymatic approaches are valuable methods in this context due to the inherent specificity of the deployed enzymes and the mild conditions of the modification reactions. One of the most common strategies is based on the transpeptidation catalyzed by sortase A derived from Staphylococcus aureus. The procedure is well established and a wide variety of applications have been published to date. Here, implementations of sortase A, which range from protein labeling using fluorescence dyes and the preparation of cyclic proteins to the modification of entire cells, are summarized. Furthermore, there is a focus on the optimization approaches established to solve the drawbacks of sortase-mediated transpeptidation.
Erscheinungsjahr
2014
Zeitschriftentitel
Chemistry (Weinheim an der Bergstrasse, Germany)
Band
20
Ausgabe
28
Seite(n)
8516-8529
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/2685748

Zitieren

Ritzefeld M. Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry (Weinheim an der Bergstrasse, Germany). 2014;20(28):8516-8529.
Ritzefeld, M. (2014). Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry (Weinheim an der Bergstrasse, Germany), 20(28), 8516-8529. doi:10.1002/chem.201402072
Ritzefeld, Markus. 2014. “Sortagging: a robust and efficient chemoenzymatic ligation strategy”. Chemistry (Weinheim an der Bergstrasse, Germany) 20 (28): 8516-8529.
Ritzefeld, M. (2014). Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry (Weinheim an der Bergstrasse, Germany) 20, 8516-8529.
Ritzefeld, M., 2014. Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry (Weinheim an der Bergstrasse, Germany), 20(28), p 8516-8529.
M. Ritzefeld, “Sortagging: a robust and efficient chemoenzymatic ligation strategy”, Chemistry (Weinheim an der Bergstrasse, Germany), vol. 20, 2014, pp. 8516-8529.
Ritzefeld, M.: Sortagging: a robust and efficient chemoenzymatic ligation strategy. Chemistry (Weinheim an der Bergstrasse, Germany). 20, 8516-8529 (2014).
Ritzefeld, Markus. “Sortagging: a robust and efficient chemoenzymatic ligation strategy”. Chemistry (Weinheim an der Bergstrasse, Germany) 20.28 (2014): 8516-8529.

22 Zitationen in Europe PMC

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Jia X, Kwon S, Wang CI, Huang YH, Chan LY, Tan CC, Rosengren KJ, Mulvenna JP, Schroeder CI, Craik DJ., J. Biol. Chem. 289(10), 2014
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Real-Time Analysis of Specific Protein-DNA Interactions with Surface Plasmon Resonance.
Ritzefeld M, Sewald N., J Amino Acids 2012(), 2012
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Analysis of DNA interactions using single-molecule force spectroscopy.
Ritzefeld M, Walhorn V, Anselmetti D, Sewald N., Amino Acids 44(6), 2013
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Immunosensor with a controlled orientation of antibodies by using NeutrAvidin-protein A complex at immunoaffinity layer.
Chung JW, Park JM, Bernhardt R, Pyun JC., J. Biotechnol. 126(3), 2006
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Highly oriented recombinant glycosyltransferases: site-specific immobilization of unstable membrane proteins by using Staphylococcus aureus sortase A.
Ito T, Sadamoto R, Naruchi K, Togame H, Takemoto H, Kondo H, Nishimura S., Biochemistry 49(11), 2010
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Sortase A-catalyzed site-specific coimmobilization on microparticles via streptavidin.
Matsumoto T, Tanaka T, Kondo A., Langmuir 28(7), 2012
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Covalent attachment of proteins to solid supports and surfaces via Sortase-mediated ligation.
Chan L, Cross HF, She JK, Cavalli G, Martins HF, Neylon C., PLoS ONE 2(11), 2007
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Immobilization of proteins to biacore sensor chips using Staphylococcus aureus sortase A.
Clow F, Fraser JD, Proft T., Biotechnol. Lett. 30(9), 2008
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Development of an influenza virus protein array using Sortagging technology.
Sinisi A, Popp MW, Antos JM, Pansegrau W, Savino S, Nissum M, Rappuoli R, Ploegh HL, Buti L., Bioconjug. Chem. 23(6), 2012
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Sortase A as a tool to functionalize surfaces.
Sijbrandij T, Cukkemane N, Nazmi K, Veerman EC, Bikker FJ., Bioconjug. Chem. 24(5), 2013
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End-point immobilization of recombinant thrombomodulin via sortase-mediated ligation.
Jiang R, Weingart J, Zhang H, Ma Y, Sun XL., Bioconjug. Chem. 23(3), 2012
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Leung, Angew. Chem. 124(), 2012
Bio-click chemistry: enzymatic functionalization of PEGylated capsules for targeting applications.
Leung MK, Hagemeyer CE, Johnston AP, Gonzales C, Kamphuis MM, Ardipradja K, Such GK, Peter K, Caruso F., Angew. Chem. Int. Ed. Engl. 51(29), 2012
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New method for site-specific modification of liposomes with proteins using sortase A-mediated transpeptidation.
Guo X, Wu Z, Guo Z., Bioconjug. Chem. 23(3), 2012
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Site-specific, covalent incorporation of Tus, a DNA-binding protein, on ionic-complementary self-assembling peptide hydrogels using transpeptidase Sortase A as a conjugation tool†Dedicated to the memory of Joachim H. G. Steinke.‡Electronic supplementary information (ESI) available: Further experimental data. See DOI: 10.1039/c3sm00131hClick here for additional data file.
Piluso S, Cassell HC, Gibbons JL, Waller TE, Plant NJ, Miller AF, Cavalli G., Soft Matter 9(29), 2013
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A biosynthetic strategy for re-engineering the Staphylococcus aureus cell wall with non-native small molecules.
Nelson JW, Chamessian AG, McEnaney PJ, Murelli RP, Kazmierczak BI, Kazmiercak BI, Spiegel DA., ACS Chem. Biol. 5(12), 2010
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Site-specific protein modification on living cells catalyzed by Sortase.
Tanaka T, Yamamoto T, Tsukiji S, Nagamune T., Chembiochem 9(5), 2008
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Expansion of the sortase-mediated labeling method for site-specific N-terminal labeling of cell surface proteins on living cells.
Yamamoto T, Nagamune T., Chem. Commun. (Camb.) (9), 2009
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Protein cell-surface display through in situ enzymatic modification of proteins with a poly(Ethylene glycol)-lipid.
Tomita U, Yamaguchi S, Maeda Y, Chujo K, Minamihata K, Nagamune T., Biotechnol. Bioeng. 110(10), 2013
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Anchoring foreign substances on live cell surfaces using Sortase A specific binding peptide.
Park K, Jung J, Son J, Kim SH, Chung BH., Chem. Commun. (Camb.) 49(83), 2013
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M13 bacteriophage display framework that allows sortase-mediated modification of surface-accessible phage proteins.
Hess GT, Cragnolini JJ, Popp MW, Allen MA, Dougan SK, Spooner E, Ploegh HL, Belcher AM, Guimaraes CP., Bioconjug. Chem. 23(7), 2012
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Probing the recognition of post-translational modifications by combining sortase-mediated ligation and phage-assisted selection.
Teschke T, Geltinger B, Dose A, Freund C, Schwarzer D., ACS Chem. Biol. 8(8), 2013
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Analysis of the substrate specificity of the Staphylococcus aureus sortase transpeptidase SrtA.
Kruger RG, Otvos B, Frankel BA, Bentley M, Dostal P, McCafferty DG., Biochemistry 43(6), 2004
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Sorting of LPXTG peptides by archetypal sortase A: role of invariant substrate residues in modulating the enzyme dynamics and conformational signature of a productive substrate.
Biswas T, Pawale VS, Choudhury D, Roy RP., Biochemistry 53(15), 2014
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Directed evolution of sortase A mutants with altered substrate selectivity profiles.
Piotukh K, Geltinger B, Heinrich N, Gerth F, Beyermann M, Freund C, Schwarzer D., J. Am. Chem. Soc. 133(44), 2011
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Amide bonds assemble pili on the surface of bacilli.
Budzik JM, Marraffini LA, Souda P, Whitelegge JP, Faull KF, Schneewind O., Proc. Natl. Acad. Sci. U.S.A. 105(29), 2008
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Anchoring of surface proteins to the cell wall of Staphylococcus aureus. Sortase catalyzed in vitro transpeptidation reaction using LPXTG peptide and NH(2)-Gly(3) substrates.
Ton-That H, Mazmanian SK, Faull KF, Schneewind O., J. Biol. Chem. 275(13), 2000
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Isopeptide ligation catalyzed by quintessential sortase A: mechanistic cues from cyclic and branched oligomers of indolicidin.
Dasgupta S, Samantaray S, Sahal D, Roy RP., J. Biol. Chem. 286(27), 2011
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Enhancement of sortase A-mediated protein ligation by inducing a β-hairpin structure around the ligation site.
Yamamura Y, Hirakawa H, Yamaguchi S, Nagamune T., Chem. Commun. (Camb.) 47(16), 2011
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Williamson, Angew. Chem. 124(), 2012
Efficient N-terminal labeling of proteins by use of sortase.
Williamson DJ, Fascione MA, Webb ME, Turnbull WB., Angew. Chem. Int. Ed. Engl. 51(37), 2012
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Depsipeptide substrates for sortase-mediated N-terminal protein ligation.
Williamson DJ, Webb ME, Turnbull WB., Nat Protoc 9(2), 2014
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Irreversible sortase A-mediated ligation driven by diketopiperazine formation.
Liu F, Luo EY, Flora DB, Mezo AR., J. Org. Chem. 79(2), 2014
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Li, Angew. Chem. 126(), 2014
Irreversible site-specific hydrazinolysis of proteins by use of sortase.
Li YM, Li YT, Pan M, Kong XQ, Huang YC, Hong ZY, Liu L., Angew. Chem. Int. Ed. Engl. 53(8), 2014
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Design of Ca2+-independent Staphylococcus aureus sortase A mutants.
Hirakawa H, Ishikawa S, Nagamune T., Biotechnol. Bioeng. 109(12), 2012
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AUTHOR UNKNOWN, 0
Cooperative binding of PhoB(DBD) to its cognate DNA sequence-a combined application of single-molecule and ensemble methods.
Ritzefeld M, Walhorn V, Kleineberg C, Bieker A, Kock K, Herrmann C, Anselmetti D, Sewald N., Biochemistry 52(46), 2013
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Large scale modification of biomolecules using immobilized sortase A from Staphylococcus aureus.
Steinhagen M, Zunker K, Nordsieck K, Beck-Sickinger AG., Bioorg. Med. Chem. 21(12), 2013
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Staphylococcus aureus sortase A exists as a dimeric protein in vitro.
Lu C, Zhu J, Wang Y, Umeda A, Cowmeadow RB, Lai E, Moreno GN, Person MD, Zhang Z., Biochemistry 46(32), 2007
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Bellucci, Angew. Chem. 125(), 2013
Three-in-one chromatography-free purification, tag removal, and site-specific modification of recombinant fusion proteins using sortase A and elastin-like polypeptides.
Bellucci JJ, Amiram M, Bhattacharyya J, McCafferty D, Chilkoti A., Angew. Chem. Int. Ed. Engl. 52(13), 2013
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A general strategy for the evolution of bond-forming enzymes using yeast display.
Chen I, Dorr BM, Liu DR., Proc. Natl. Acad. Sci. U.S.A. 108(28), 2011
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AUTHOR UNKNOWN, 0

Deng, Angew. Chem. 126(), 2014
Total chemical synthesis of the enzyme sortase A(ΔN59) with full catalytic activity.
Deng FK, Zhang L, Wang YT, Schneewind O, Kent SB., Angew. Chem. Int. Ed. Engl. 53(18), 2014
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