Selective Exo-Enzymatic Labeling of N-Glycans on the Surface of Living Cells by Recombinant ST6Gal I†
Dr. Ngalle Eric Mbua
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Chemistry, University of Georgia (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Xiuru Li
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Heather R. Flanagan-Steet
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorDr. Lu Meng
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorDr. Kazuhiro Aoki
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorProf. Dr. Kelley W. Moremen
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Biochemistry and Molecular Biology, University of Georgia (USA)
Search for more papers by this authorDr. Margreet A. Wolfert
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Richard Steet
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Biochemistry and Molecular Biology, University of Georgia (USA)
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)===Search for more papers by this authorCorresponding Author
Prof. Dr. Geert-Jan Boons
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Chemistry, University of Georgia (USA)
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)===Search for more papers by this authorDr. Ngalle Eric Mbua
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Chemistry, University of Georgia (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Xiuru Li
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Heather R. Flanagan-Steet
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorDr. Lu Meng
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorDr. Kazuhiro Aoki
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorProf. Dr. Kelley W. Moremen
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Biochemistry and Molecular Biology, University of Georgia (USA)
Search for more papers by this authorDr. Margreet A. Wolfert
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Richard Steet
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Biochemistry and Molecular Biology, University of Georgia (USA)
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)===Search for more papers by this authorCorresponding Author
Prof. Dr. Geert-Jan Boons
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)
Department of Chemistry, University of Georgia (USA)
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA)===Search for more papers by this authorThis research was supported by the National Cancer Institute (R01CA088986 to G.-J.B.), the National Center for Research Resources (P41RR005351 to G.-J.B. and K.W.M.) and the National Institute of General Medical Sciences (P41GM103390 to G.-J.B. and K.W.M.; R01GM086524 to R.S.; P41GM103490 to K.A.) from the US National Institutes of Health.
Graphical Abstract
A game of tag: N-Glycans on the surface of living cells were selectively tagged by exogenously administering recombinant ST6Gal I sialyltransferase and azide-modified CMP-Neu5Ac. This modification was followed by a strain-promoted cycloaddition using a biotin-modified dibenzylcyclooctynol (red star=biotin). The methodology will make it possible to dissect the mechanisms that underlie altered glycoconjugate recycling and storage in disease.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie_201307095_sm_miscellaneous_information.pdf5.2 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aE. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108–7133;
10.1002/ange.200900942 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 6974–6998;
- 1bG. J. Boons in Carbohydrate Chemistry: Chemical and Biological Approaches, Vol. 36 (Eds.: ), RSC Publishing, Cambridge, 2010, pp. 152–167.
- 2M. F. Debets, C. W. J. van der Doelen, F. P. J. T. Rutjes, F. L. van Delft, ChemBioChem 2010, 11, 1168–1184.
- 3
- 3aE. Saxon, C. R. Bertozzi, Science 2000, 287, 2007–2010;
- 3bC. I. Schilling, N. Jung, M. Biskup, U. Schepers, S. Brase, Chem. Soc. Rev. 2011, 40, 4840–4871.
- 4
- 4aM. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952–3015;
- 4bD. Soriano Del Amo, W. Wang, H. Jiang, C. Besanceney, A. C. Yan, M. Levy, Y. Liu, F. L. Marlow, P. Wu, J. Am. Chem. Soc. 2010, 132, 16893–16899;
- 4cD. C. Kennedy, C. S. McKay, M. C. Legault, D. C. Danielson, J. A. Blake, A. F. Pegoraro, A. Stolow, Z. Mester, J. P. Pezacki, J. Am. Chem. Soc. 2011, 133, 17993–18001.
- 5
- 5aJ. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272–1279;
- 5bM. F. Debets, S. S. van Berkel, J. Dommerholt, A. T. Dirks, F. P. Rutjes, F. L. van Delft, Acc. Chem. Res. 2011, 44, 805–815.
- 6
- 6aA. Hara, N. Kitazawa, T. Taketomi, J. Lipid Res. 1984, 25, 175–184;
- 6bR. McGlynn, K. Dobrenis, S. U. Walkley, J. Comp. Neurol. 2004, 480, 415–426.
- 7
- 7aJ. Roth, D. J. Taatjes, J. M. Lucocq, J. Weinstein, J. C. Paulson, Cell 1985, 43, 287–295;
- 7bF. Dall’Olio, Glycoconjugate J. 2000, 17, 669–676;
- 7cY. Zhuo, S. L. Bellis, J. Biol. Chem. 2011, 286, 5935–5941.
- 8Y. Kajihara, T. Kamitani, R. Sato, N. Kamei, T. Miyazaki, R. Okamoto, T. Sakakibara, T. Tsuji, T. Yamamoto, Carbohydr. Res. 2007, 342, 1680–1688.
- 9H. Yu, H. Yu, R. Karpel, X. Chen, Bioorg. Med. Chem. 2004, 12, 6427–6435.
- 10F. Friscourt, P. A. Ledin, N. E. Mbua, H. R. Flanagan-Steet, M. A. Wolfert, R. Steet, G. J. Boons, J. Am. Chem. Soc. 2012, 134, 5381–5389.
- 11
- 11aD. H. Joziasse, W. E. Schiphorst, D. H. van den Eijnden, J. A. van Kuik, H. van Halbeek, J. F. Vliegenthart, J. Biol. Chem. 1985, 260, 714–719;
- 11bF. Maley, R. B. Trimble, A. L. Tarentino, T. H. Plummer, Jr., Anal. Biochem. 1989, 180, 195–204;
- 11cT. L. Chen, C. Chen, N. Q. Bergeron, B. E. Close, T. J. Bohrer, B. M. Vertel, K. J. Colley, Glycobiology 2003, 13, 109–117;
- 11dA. W. Barb, L. Meng, Z. Gao, R. W. Johnson, K. W. Moremen, J. H. Prestegard, Biochemistry 2012, 51, 4618–4626.
- 12K. R. Anumula, P. B. Taylor, Anal. Biochem. 1992, 203, 101–108.
- 13M. R. Bond, C. M. Whitman, J. J. Kohler, Mol. BioSyst. 2010, 6, 1796–1799.
- 14
- 14aA. D. Elbein, J. E. Tropea, M. Mitchell, G. P. Kaushal, J. Biol. Chem. 1990, 265, 15599–15605;
- 14bF. Vallee, K. Karaveg, A. Herscovics, K. W. Moremen, P. L. Howell, J. Biol. Chem. 2000, 275, 41287–41298.
- 15
- 15aX. H. Ning, J. Guo, M. A. Wolfert, G. J. Boons, Angew. Chem. 2008, 120, 2285–2287; Angew. Chem. Int. Ed. 2008, 47, 2253–2255;
- 15bN. E. Mbua, J. Guo, M. A. Wolfert, R. Steet, G. J. Boons, ChemBioChem 2011, 12, 1912–1921.
- 16C. T. Anderson, I. S. Wallace, C. R. Somerville, Proc. Natl. Acad. Sci. USA 2012, 109, 1329–1334.
- 17A. Dumont, A. Malleron, M. Awwad, S. Dukan, B. Vauzeilles, Angew. Chem. 2012, 124, 3197–3200;
10.1002/ange.201108127 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 3143–3146.
- 18
- 18aN. Khidekel, S. B. Ficarro, P. M. Clark, M. C. Bryan, D. L. Swaney, J. E. Rexach, Y. E. Sun, J. J. Coon, E. C. Peters, L. C. Hsieh-Wilson, Nat. Chem. Biol. 2007, 3, 339–348;
- 18bP. M. Clark, J. F. Dweck, D. E. Mason, C. R. Hart, S. B. Buck, E. C. Peters, B. J. Agnew, L. C. Hsieh-Wilson, J. Am. Chem. Soc. 2008, 130, 11576–11577;
- 18cN. Mercer, B. Ramakrishnan, E. Boeggeman, L. Verdi, P. K. Qasba, Bioconjugate Chem. 2013, 24, 144–152.
- 19T. Zheng, H. Jiang, M. Gros, D. Soriano del Amo, S. Sundaram, G. Lauvau, F. Marlow, Y. Liu, P. Stanley, P. Wu, Angew. Chem. 2011, 123, 4199; Angew. Chem. Int. Ed. 2011, 50, 4113.
- 20
- 20aA. H. Futerman, G. van Meer, Nat. Rev. Mol. Cell Biol. 2004, 5, 554–565;
- 20bS. BasuRay, S. Mukherjee, E. G. Romero, M. N. Seaman, A. Wandinger-Ness, J. Biol. Chem. 2013, 288, 1135–1149.
- 21
- 21aA. Harduin-Lepers, V. Vallejo-Ruiz, M. A. Krzewinski-Recchi, B. Samyn-Petit, S. Julien, P. Delannoy, Biochimie 2001, 83, 727–737;
- 21bA. Harduin-Lepers, R. Mollicone, P. Delannoy, R. Oriol, Glycobiology 2005, 15, 805–817;
- 21cS. Takashima, Biosci. Biotechnol. Biochem. 2008, 72, 1155–1167.
