Evaluation of analogues of GalNAc as substrates for enzymes of the Mammalian GalNAc salvage pathway

ACS Chemical Biology

Volumn 7, Issue 4, 2012, Pages 753-760

  Pouilly, Sabrina ^a   Bourgeaux, Vanessa ^a,b   Piller, Friedrich ^a   Piller, Véronique ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^b ERYTECH PHARMA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOKINASE; GALACTOKINASE 2; GLYCOLIPID; GLYCOPROTEIN; GLYCOSYLTRANSFERASE; N ACETYLGALACTOSAMINE; PROTEOGLYCAN; SUGAR NUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CELL SURFACE; CONTROLLED STUDY; ENZYME METABOLISM; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; ENZYME SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

ACETYLGALACTOSAMINE; ANIMALS; GLYCOSYLATION; GLYCOSYLTRANSFERASES; HUMANS; METABOLIC NETWORKS AND PATHWAYS; POLYSACCHARIDES; SUBSTRATE SPECIFICITY;

EID: 84860208701     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb200511t     Document Type: Article

References (41)

1. Gross, H. J., Rose, U., Krause, J. M., Paulson, J. C., Schmid, K., Feeney, R. E., and Brossmer, R. (1989) Transfer of synthetic sialic acid analogues to N-and O-linked glycoprotein glycans using four different mammalian sialyltransferases Biochemistry 28, 7386-7392 (Pubitemid 19227380)
2. Kayser, H., Zeitler, R., Kannicht, C., Grunow, D., Nuck, R., and Reutter, W. (1992) Biosynthesis of a nonphysiological sialic acid in different rat organs, using N -propanoyl- d -hexosamines as precursors J. Biol. Chem. 267, 16934-16938
3. 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
4. Wang, Z., Du, J., Che, P. L., Meledeo, M. A., and Yarema, K. J. (2009) Hexosamine analogs: from metabolic glycoengineering to drug discovery Curr. Opin. Chem. Biol. 13, 565-572
5. 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 (Pubitemid 37517979)
6. Vocadlo, D. J., Hang, H. C., Kim, E. J., Hanover, J. A., and Bertozzi, C. R. (2003) A chemical approach for identifying O-GlcNAc-modified proteins in cells Proc. Natl. Acad. Sci. U.S.A. 100, 9116-9121 (Pubitemid 37033892)
7. Kayser, H., Geilen, C. C., Paul, C., Zeitler, R., and Reutter, W. (1992) Incorporation of N -acyl-2-amino-2-deoxy-hexoses into glycosphingolipids of the pheochromocytoma cell line PC 12 FEBS Lett. 301, 137-140
8. Laughlin, S. T. and Bertozzi, C. R. (2009) In vivo imaging of Caenorhabditis elegans glycans ACS Chem. Biol. 4, 1068-1072
9. Baskin, J. M., Dehnert, K. W., Laughlin, S. T., Amacher, S. L., and Bertozzi, C. R. (2010) Visualizing enveloping layer glycans during zebrafish early embryogenesis Proc. Natl. Acad. Sci. U.S.A. 107, 10360-10365
10. Laughlin, S. T. and Bertozzi, C. R. (2007) Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation Nat. Protoc. 2, 2930-2944
11. 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 (Pubitemid 350210944)
12. Marathe, D. D., Buffone, A., Jr., Chandrasekaran, E. V., Xue, J., Locke, R. D., Nasirikenari, M., Lau, J. T., Matta, K. L., and Neelamegham, S. (2010) Fluorinated per-acetylated GalNAc metabolically alters glycan structures on leukocyte PSGL-1 and reduces cell binding to selectins Blood 115, 1303-1312
13. Descheny, L., Gainers, M. E., Walcheck, B., and Dimitroff, C. J. (2006) Ameliorating skin-homing receptors on malignant T cells with a fluorosugar analog of N -acetylglucosamine: P-selectin ligand is a more sensitive target than E-selectin ligand J. Invest. Dermatol. 126, 2065-2073
14. Guo, Z. and Wang, Q. (2009) Recent development in carbohydrate-based cancer vaccines Curr. Opin. Chem. Biol. 13, 608-617
15. Maley, F., Tarentino, A. L., McGarrahan, J. F., and Delgiacco, R. (1968) The metabolism of d -galactosamine and N -acetyl- d -galactosamine in rat liver Biochem. J. 107, 637-644
16. Gamblin, D. P., Scanlan, E. M., and Davis, B. G. (2009) Glycoprotein synthesis: an update Chem. Rev. 109, 131-163
17. Bourgeaux, V., Piller, F., and Piller, V. (2005) Two-step enzymatic synthesis of UDP- N -acetylgalactosamine Bioorg. Med. Chem. Lett. 15, 5459-5462 (Pubitemid 41562970)
18. Cai, L., Guan, W., Wang, W., Zhao, W., Kitaoka, M., Shen, J., O'Neil, C., and Wang, P. G. (2009) Substrate specificity of N -acetylhexosamine kinase towards N -acetylgalactosamine derivatives Bioorg. Med. Chem. Lett. 19, 5433-5435
19. Busca, P. and Martin, O. R. (2004) Synthesis of UDP-GalNAc analogues as probes for glycosyltransferases. Part 2 Tetrahedron Lett. 45, 4433-4436 (Pubitemid 38610359)
20. Berkin, A., Szarek, W. A., and Kisilevsky, R. (2000) Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy- d -glucose and 2-acetamido-2-deoxy- d -galactose and their effects on cellular glycosaminoglycan biosynthesis Carbohydr. Res. 326, 250-263 (Pubitemid 30386914)
21. Pastuszak, I., Drake, R., and Elbein, A. D. (1996) Kidney N -acetylgalactosamine (GalNAc)-1-phosphate kinase, a new pathway of GalNAc activation J. Biol. Chem. 271, 20776-20782 (Pubitemid 26281863)
22. Thoden, J. B. and Holden, H. M. (2005) The molecular architecture of human N -acetylgalactosamine kinase J. Biol. Chem. 280, 32784-32791 (Pubitemid 41368325)
23. Nishimoto, M. and Kitaoka, M. (2007) Identification of N -acetylhexosamine 1-kinase in the complete lacto- N -biose I/galacto- N -biose metabolic pathway in Bifidobacterium longum Appl. Environ. Microbiol. 73, 6444-6449 (Pubitemid 47623702)
24. Peneff, C., Ferrari, P., Charrier, V., Taburet, Y., Monnier, C., Zamboni, V., Winter, J., Harnois, M., Fassy, F., and Bourne, Y. (2001) Crystal structures of two human pyrophosphorylase isoforms in complexes with UDPGlc(Gal)NAc: role of the alternatively spliced insert in the enzyme oligomeric assembly and active site architecture EMBO J. 20, 6191-6202 (Pubitemid 33078693)
25. Guan, W., Cai, L., Fang, J., Wu, B., and Wang, P. G. (2009) Enzymatic synthesis of UDP-GlcNAc/UDP-GalNAc analogs using N -acetylglucosamine 1-phosphate uridyltransferase (GlmU) Chem. Commun. 6976-6978
26. Feng, F., Okuyama, K., Niikura, K., Ohta, T., Sadamoto, R., Monde, K., Noguchi, T., and Nishimura, S. (2004) Chemo-enzymatic synthesis of fluorinated 2- N -acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase Org Biomol Chem 2, 1617-1623
27. Guan, W., Cai, L., and Wang, P. G. (2010) Highly efficient synthesis of UDP-GalNAc/GlcNAc analogues with promiscuous recombinant human UDP-GalNAc pyrophosphorylase AGX1 Chemistry 16, 13343-13345
28. Kingsley, P. D., Hagen, K. G., Maltby, K. M., Zara, J., and Tabak, L. A. (2000) Diverse spatial expression patterns of UDP-GalNAc:polypeptide N -acetylgalactosaminyl-transferase family member mRNAs during mouse development Glycobiology 10, 1317-1323 (Pubitemid 32124329)
29. Duclos, S., Da Silva, P., Vovelle, F., Piller, F., and Piller, V. (2004) Characterization of the UDP- N -acetylgalactosamine binding domain of bovine polypeptide alpha N -acetylgalactosaminyltransferase T1 Protein Eng., Des. Sel. 17, 635-646 (Pubitemid 39665400)
30. Busca, P., Piller, V., Piller, F., and Martin, O. R. (2003) Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-alpha-GalNAc-transferases Bioorg. Med. Chem. Lett. 13, 1853-1856 (Pubitemid 36577127)
31. Hang, H. C., Yu, C., Pratt, M. R., and Bertozzi, C. R. (2004) Probing glycosyltransferase activities with the Staudinger ligation J. Am. Chem. Soc. 126, 6-7 (Pubitemid 38090313)
32. Kubota, T., Shiba, T., Sugioka, S., Furukawa, S., Sawaki, H., Kato, R., Wakatsuki, S., and Narimatsu, H. (2006) Structural basis of carbohydrate transfer activity by human UDP-GalNAc: polypeptide alpha- N - acetylgalactosaminyltransferase (pp-GalNAc-T10) J. Mol. Biol. 359, 708-727 (Pubitemid 43767270)
33. Ten Hagen, K. G., Fritz, T. A., and Tabak, L. A. (2003) All in the family: the UDP-GalNAc:polypeptide N -acetylgalactosaminyltransferases Glycobiology 13, 1R-16R
34. Fritz, T. A., Hurley, J. H., Trinh, L. B., Shiloach, J., and Tabak, L. A. (2004) The beginnings of mucin biosynthesis: the crystal structure of UDP-GalNAc:polypeptide alpha- N -acetylgalactosaminyltransferase-T1 Proc. Natl. Acad. Sci. U.S.A. 101, 15307-15312 (Pubitemid 39441537)
35. Hagen, F. K., Hazes, B., Raffo, R., deSa, D., and Tabak, L. A. (1999) Structure-function analysis of the UDP- N -acetyl- d -galactosamine:polypeptide N -acetylgalactosaminyltransferase. Essential residues lie in a predicted active site cleft resembling a lactose repressor fold J. Biol. Chem. 274, 6797-6803 (Pubitemid 29111104)
36. Kingsley, D. M., Kozarsky, K. F., Hobbie, L., and Krieger, M. (1986) Reversible defects in O -linked glycosylation and LDL receptor expression in a UDP-Gal/UDP-GalNAc 4-epimerase deficient mutant Cell 44, 749-759 (Pubitemid 16073971)
37. Tollefsen, S. E. and Kornfeld, R. (1983) The B4 lectin from Vicia villosa seeds interacts with N -acetylgalactosamine residues alpha-linked to serine or threonine residues in cell surface glycoproteins J. Biol. Chem. 258, 5172-5176
38. 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
39. Barthel, S. R., Antonopoulos, A., Cedeno-Laurent, F., Schaffer, L., Hernandez, G., Patil, S. A., North, S. J., Dell, A., Matta, K. L., Neelamegham, S., Haslam, S. M., and Dimitroff, C. J. (2011) Peracetylated 4-fluoro-glucosamine reduces the content and repertoire of N-and O -glycans without direct incorporation J. Biol. Chem. 286, 21717-21731
40. Cremer, G. A., Bureaud, N., Piller, V., Kunz, H., Piller, F., and Delmas, A. F. (2006) Synthesis and biological evaluation of a multiantigenic Tn/TF-containing glycopeptide mimic of the tumor-related MUC1 glycoprotein ChemMedChem 1, 965-968 (Pubitemid 44448795)
41. Krieger, M., Reddy, P., Kozarsky, K., Kingsley, D., Hobbie, L., and Penman, M. (1989) Analysis of the synthesis, intracellular sorting, and function of glycoproteins using a mammalian cell mutant with reversible glycosylation defects Methods Cell. Biol. 32, 57-84