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Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 285-298

http://dx.doi.org/10.1351/PAC-CON-08-11-05

Sugars and proteins: New strategies in synthetic biology

Benjamin G. Davis

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK

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  • Megia-Fernandez Alicia, de la Torre-Gonzalez Diego, Parada-Aliste Jose, Lopez-Jaramillo Francisco Javier, Hernandez-Mateo Fernando, Santoyo-Gonzalez Francisco: Masked Thiol Sugars: Chemical Behavior and Synthetic Applications of S -Glycopyranosyl-N -monoalkyl Dithiocarbamates. Chem. Asian J. 2014, 9, 620. <http://dx.doi.org/10.1002/asia.201301270>
  • Ryu Jihye, Eom Min Sik, Ko Wooseok, Han Min Su, Lee Hyun Soo: A fluorescence-based glycosyltransferase assay for high-throughput screening. Bioorganic & Medicinal Chemistry 2014, 22, 2571. <http://dx.doi.org/10.1016/j.bmc.2014.02.027>
  • Boutureira Omar, Bernardes Gonçalo J. L., Fernández-González Marta, Anthony Daniel C., Davis Benjamin G.: Selenenylsulfide-Linked Homogeneous Glycopeptides and Glycoproteins: Synthesis of Human “Hepatic Se Metabolite A”. angew chemie 2012, 124, 1461. <http://dx.doi.org/10.1002/ange.201106658>
  • Boutureira Omar, Bernardes Gonçalo J. L., Fernández-González Marta, Anthony Daniel C., Davis Benjamin G.: Selenenylsulfide-Linked Homogeneous Glycopeptides and Glycoproteins: Synthesis of Human “Hepatic Se Metabolite A”. Angew Chem Int E 2012, 51, 1432. <http://dx.doi.org/10.1002/anie.201106658>
  • Spicer Christopher D., Triemer Therese, Davis Benjamin G.: Palladium-Mediated Cell-Surface Labeling. J. Am. Chem. Soc. 2012, 134, 800. <http://dx.doi.org/10.1021/ja209352s>
  • Kung Karen Ka-Yan, Li Gai-Li, Zou Lan, Chong Hiu-Chi, Leung Yun-Chung, Wong Ka-Hing, Lo Vanessa Kar-Yan, Che Chi-Ming, Wong Man-Kin: Gold-mediated bifunctional modification of oligosaccharides via a three-component coupling reaction. Biomol Chem 2012, 10, 925. <http://dx.doi.org/10.1039/c1ob06429k>
  • Bernardes Gonçalo J. L., Linderoth Lars, Doores Katie J., Boutureira Omar, Davis Benjamin G.: Site-Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations. Chem Eur J of Chem Bio 2011, 12, 1383. <http://dx.doi.org/10.1002/cbic.201100125>
  • Lee Hyun Soo, Thorson Jon S.: Development of a universal glycosyltransferase assay amenable to high-throughput formats. Anal Bichem 2011, 418, 85. <http://dx.doi.org/10.1016/j.ab.2011.06.016>
  • Szabó Tamás, Szilágyi László, Illyés Tünde-Zita: Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents. Carbohydrates Research 2011, 346, 1622. <http://dx.doi.org/10.1016/j.carres.2011.04.020>
  • Díaz-Rodríguez Alba, Davis Benjamin G: Chemical modification in the creation of novel biocatalysts. J Curr Opin Chem Biol 2011, 15, 211. <http://dx.doi.org/10.1016/j.cbpa.2010.12.002>
  • Chalker Justin M., Bernardes Gonçalo J. L., Davis Benjamin G.: A “Tag-and-Modify” Approach to Site-Selective Protein Modification. Acc. Chem. Res. 2011, 44, 730. <http://dx.doi.org/10.1021/ar200056q>
  • Vallée M. Robert J., Majkut Paul, Wilkening Ina, Weise Christoph, Müller Gregor, Hackenberger Christian P. R.: Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins. Org Lett 2011, 13, 5440. <http://dx.doi.org/10.1021/ol2020175>
  • Spicer Christopher D., Davis Benjamin G.: Palladium-mediated site-selective Suzuki–Miyaura protein modification at genetically encoded aryl halides. Chem Commun 2011, 47, 1698. <http://dx.doi.org/10.1039/c0cc04970k>
  • Galan M. Carmen, Benito-Alifonso David, Watt Gregory M.: Carbohydrate chemistry in drug discovery. Org Biomol Chem 2011, 9, 3598. <http://dx.doi.org/10.1039/c0ob01017k>
  • Boutureira Omar, Bernardes Gonçalo J. L., D'Hooge François, Davis Benjamin G.: Direct radiolabelling of proteins at cysteine using [18F]-fluorosugars. Chemical Communication 2011, 47, 10010. <http://dx.doi.org/10.1039/c1cc13524d>
  • Conte Mauro Lo, Staderini Samuele, Marra Alberto, Sanchez-Navarro Macarena, Davis Benjamin G., Dondoni Alessandro: Multi-molecule reaction of serum albumin can occur through thiol-yne coupling. Chem Commn 2011, 47, 11086. <http://dx.doi.org/10.1039/c1cc14402b>
  • Chalker Justin M., Gunnoo Smita B., Boutureira Omar, Gerstberger Stefanie C., Fernández-González Marta, Bernardes Gonçalo J. L., Griffin Laura, Hailu Hanna, Schofield Christopher J., Davis Benjamin G.: Methods for converting cysteine to dehydroalanine on peptides and proteins. Chem Sci 2011, 2, 1666. <http://dx.doi.org/10.1039/c1sc00185j>
  • Chalker Justin M, Davis Benjamin G: Chemical mutagenesis: selective post-expression interconversion of protein amino acid residues. J Curr Opin Chem Biol 2010, 14, 781. <http://dx.doi.org/10.1016/j.cbpa.2010.10.007>
  • Böhrsch Verena, Serwa Remigiusz, Majkut Paul, Krause Eberhard, Hackenberger Christian P. R.: Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites. Chem Commun 2010, 46, 3176. <http://dx.doi.org/10.1039/b926818a>
  • Boutureira Omar, D'Hooge François, Fernández-González Marta, Bernardes Gonçalo J. L., Sánchez-Navarro Macarena, Koeppe Julia R., Davis Benjamin G.: Fluoroglycoproteins: ready chemical site-selective incorporation of fluorosugars into proteins. Chem Commun 2010, 46, 8142. <http://dx.doi.org/10.1039/c0cc01576h>
  • Patel Mitul K., Vijayakrishnan Balakumar, Koeppe Julia R., Chalker Justin M., Doores Katie J., Davis Benjamin G.: Analysis of the dispersity in carbohydrate loading of synthetic glycoproteins using MALDI-TOF mass spectrometry. Chem Commun 2010, 46, 9119. <http://dx.doi.org/10.1039/c0cc03420g>
  • Fernández-González Marta, Boutureira Omar, Bernardes Gonçalo J. L., Chalker Justin M., Young Matthew A., Errey James C., Davis Benjamin G.: Site-selective chemoenzymatic construction of synthetic glycoproteins using endoglycosidases. Chem Sci 2010, 1, 709. <http://dx.doi.org/10.1039/c0sc00265h>
  • Serwa Remigiusz, Majkut Paul, Horstmann Benjamin, Swiecicki Jean-Marie, Gerrits Michael, Krause Eberhard, Hackenberger Christian P. R.: Site-specific PEGylation of proteins by a Staudinger-phosphite reaction. Chem Sci 2010, 1, 596. <http://dx.doi.org/10.1039/c0sc00324g>
  • Floyd Nicola, Vijayakrishnan Balakumar, Koeppe Julia R., Davis Benjamin G.: Thiyl Glycosylation of Olefinic Proteins: S-Linked Glycoconjugate Synthesis. Angew Chem 2009, 121, 7938. <http://dx.doi.org/10.1002/ange.200903135>
  • Floyd Nicola, Vijayakrishnan Balakumar, Koeppe Julia R., Davis Benjamin G.: Thiyl Glycosylation of Olefinic Proteins: S-Linked Glycoconjugate Synthesis. Angew Chem Int Ed 2009, 48, 7798. <http://dx.doi.org/10.1002/anie.200903135>
  • Dondoni Alessandro, Massi Alessandro, Nanni Paolo, Roda Aldo: A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol-Ene Coupling. Chem. Eur. J. 2009, 15, 11444. <http://dx.doi.org/10.1002/chem.200901746>
  • Russell David, Oldham Neil J., Davis Benjamin G.: Site-selective chemical protein glycosylation protects from autolysis and proteolytic degradation. Carbohydrates Research 2009, 344, 1508. <http://dx.doi.org/10.1016/j.carres.2009.06.033>
  • Chalker Justin M., Wood Charlotte S. C., Davis Benjamin G.: A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling. J Am Chem Soc 2009, 131, 16346. <http://dx.doi.org/10.1021/ja907150m>
  • Chalker Justin M., Lin Yuya A., Boutureira Omar, Davis Benjamin G.: Enabling olefin metathesis on proteins: chemical methods for installation of S-allyl cysteine. Chem Commun 2009, 3714. <http://dx.doi.org/10.1039/b908004j>