N-Azidoacetylmannosamine and N-Azidoacetylgalactosamine Incorporation into N-Glycans of Recombinantly Expressed Human Lactotransferrin by Metabolic Oligosaccharide Engineering

REFERENCES

• Sinclair , A. M. and Elliott , S. 2005 . Glycoengineering: the effect of glycosylation on the properties of therapeutic proteins . J. Pharm. Sci. , 94 : 1626 – 1635 .
   PubMed Web of Science ®Google Scholar
• Du , J. , Meledeo , M. A. , Wang , Z. , Khanna , H. S. , Paruchuri , V. D. and Yarema , K. J. 2009 . Metabolic glycoengineering: sialic acid and beyond . Glycobiology , 19 : 1382 – 1401 .
   PubMed Web of Science ®Google Scholar
• de Mejia , E. G. and Dia , V. P. 2010 . The role of nutraceutical proteins and peptides in apoptosis, angiogenesis, and metastasis of cancer cells . Cancer Metastasis Rev. , 29 : 511 – 528 .
   PubMed Web of Science ®Google Scholar
• Gonzalez-Chavez , S. A. , Arevalo-Gallegos , S. and Rascon-Cruz , Q. 2009 . Lactoferrin: structure, function and applications . Int. J. Antimicrob. Agents , 33 : 301 – 308 .
   PubMed Web of Science ®Google Scholar
• Yu , T. , Guo , C. , Wang , J. , Hao , P. , Sui , S. , Chen , X. , Zhang , R. , Wang , P. , Yu , G. , Zhang , L. , Dai , Y. and Li , N. 2011 . Comprehensive characterization of the site-specific N-glycosylation of wild-type and recombinant human lactoferrin expressed in the milk of transgenic cloned cattle . Glycobiology , 21 : 206 – 224 .
   Google Scholar
• van Berkel , P. H. , Geerts , M. E. , van Veen , H. A. , Kooiman , P. M. , Pieper , F. R. , de Boer , H. A. and Nuijens , J. H. 1995 . Glycosylated and unglycosylated human lactoferrins both bind iron and show identical affinities towards human lysozyme and bacterial lipopolysaccharide, but differ in their susceptibilities towards tryptic proteolysis . Biochem. J. , 312 : 107 – 114 .
   PubMed Web of Science ®Google Scholar
• Möller , H. , Böhrsch , V. , Lucka , L. , Hackenberger , P. R.C. and Hinderlich , S. 2011 . Efficient metabolic oligosaccharide engineering of glycoproteins by UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) knock-down . Mol. Biosyst. , 7 : 2245 – 2251 .
   Google Scholar
• Bork , K. , Horstkorte , R. and Weidemann , W. 2009 . Increasing the sialylation of therapeutic glycoproteins: the potential of the sialic acid biosynthetic pathway . J. Pharm. Sci. , 98 : 3499 – 3508 .
   PubMed Web of Science ®Google Scholar
• Nojima , Y. , Suzuki , Y. , Yoshida , K. , Abe , F. , Shiga , T. , Takeuchi , T. , Sugiyama , A. , Shimizu , H. and Sato , A. 2009 . Lactoferrin conjugated with 40-KDa branched poly(ethylene glycol) has an improved circulating half-life . Pharm. Res. , 26 : 2125 – 2132 .
   PubMed Web of Science ®Google Scholar
• Hackenberger , C. P. and Schwarzer , D. 2008 . Chemoselective ligation and modification strategies for peptides and proteins . Angew. Chem. Int. Ed Engl. , 47 : 10030 – 10074 .
   PubMed Web of Science ®Google Scholar
• Prescher , J. A. and Bertozzi , C. R. 2005 . Chemistry in living systems . Nat. Chem. Biol. , 1 : 13 – 21 .
   PubMed Web of Science ®Google Scholar
• Rostovtsev , V. V. , Green , L. G. , Fokin , V. V. and Sharpless , K. B. 2002 . A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes . Angew. Chem. Int. Ed Engl. , 41 : 2596 – 2599; .
   PubMed Web of Science ®Google Scholar
• Tornoe , C. W. , Christensen , C. and Meldal , M. 2002 . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides . J. Org. Chem. , 67 : 3057 – 3064 . For seminal contributions, see: Huisgen, R.; Szeimies, G.; Möbius, L. Kinetik der Addition organischer Azide an CC-Mehrfachbindungen (german). Chem. Ber. 1967, 100, 2494–2507
   PubMed Web of Science ®Google Scholar
• Agard , N. J. , Prescher , J. A. and Bertozzi , C. R. 2004 . A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems . J. Am. Chem. Soc. , 126 : 15046 – 15047; .
   PubMed Web of Science ®Google Scholar
• Baskin , J. M. , Prescher , J. A. , Laughlin , S. T. , Agard , N. J. , Chang , P. V. , Miller , I. A. , Lo , A. , Codelli , J. A. and Bertozzi , C. R. 2007 . Copper-free click chemistry for dynamic in vivo imaging . Proc. Natl. Acad. Sci. U S A , 104 : 16793 – 16797 .
   PubMed Web of Science ®Google Scholar
• Chitlaru , T. , Kronman , C. , Zeevi , M. , Kam , M. , Harel , A. , Ordentlich , A. , Velan , B. and Shafferman , A. 1998 . Modulation of circulatory residence of recombinant acetylcholinesterase through biochemical or genetic manipulation of sialylation levels . Biochem. J. , 336 ( Pt 3 ) : 647 – 658 .
   Google Scholar
• Jones , M. B. , Teng , H. , Rhee , J. K. , Lahar , N. , Baskaran , G. and Yarema , K. J. 2004 . Characterization of the cellular uptake and metabolic conversion of acetylated N-acetylmannosamine (ManNAc) analogues to sialic acids . Biotechnol. Bioeng. , 85 : 394 – 405 .
   Google Scholar
• Kim , E. J. , Sampathkumar , S. G. , Jones , M. B. , Rhee , J. K. , Baskaran , G. , Goon , S. and Yarema , K. J. 2004 . Characterization of the metabolic flux and apoptotic effects of O-hydroxyl- and N-acyl-modified N-acetylmannosamine analogs in Jurkat cells . J. Biol. Chem. , 279 : 18342 – 18352 .
   Google Scholar
• Hang , H. C. , Yu , C. , Kato , D. L. and Bertozzi , C. R. 2003 . A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation . Proc. Natl. Acad. Sci. U S A , 100 : 14846 – 14851 .
   PubMed Web of Science ®Google Scholar
• Ohkura , T. , Seko , A. , Hara-Kuge , S. and Yamashita , K. 2002 . Occurrence of secretory glycoprotein-specific GalNAc beta 1–>4GlcNAc sequence in N-glycans in MDCK cells . J. Biochem. , 132 : 891 – 901 .
   PubMed Web of Science ®Google Scholar
• Wedepohl , S. , Kaup , M. , Riese , S. B. , Berger , M. , Dernedde , J. , Tauber , R. and Blanchard , V. 2010 . N-Glycan analysis of recombinant L-selectin reveals sulfated GalNAc and GalNAc-GalNAc motifs . J. Proteome. Res. , 9 : 3403 – 3411 .
   PubMed Web of Science ®Google Scholar
• Yan , S. B. , Chao , Y. B. and van Halbeek , H. 1993 . Novel Asn-linked oligosaccharides terminating in GalNAc beta (1–>4)[Fuc alpha (1–>3)]GlcNAc beta (1–>.) are present in recombinant human protein C expressed in human kidney 293 cells . Glycobiology , 3 : 597 – 608 .
   Google Scholar
• Boyce , M. , Carrico , I. S. , Ganguli , A. S. , Yu , S. H. , Hangauer , M. J. , Hubbard , S. C. , Kohler , J. J. and Bertozzi , C. R. 2011 . Metabolic cross-talk allows labeling of O-linked beta-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway . Proc. Natl. Acad. Sci. U S A , 108 : 3141 – 3146 .
   PubMed Web of Science ®Google Scholar
• Saxon , E. , Luchansky , S. J. , Hang , H. C. , Yu , C. , Lee , S. C. and Bertozzi , C. R. 2002 . Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation . J. Am. Chem. Soc. , 124 : 14893 – 14902 .
   PubMed Web of Science ®Google Scholar
• Mantey , L. R. , Keppler , O. T. , Pawlita , M. , Reutter , W. and Hinderlich , S. 2001 . Efficient biochemical engineering of cellular sialic acids using an unphysiological sialic acid precursor in cells lacking UDP-N-acetylglucosamine 2-epimerase . FEBS Lett. , 503 : 80 – 84 .
   Google Scholar