Synthesis of O-glycopeptides and construction of glycopeptide microarrays

Methods in Molecular Biology

Volumn 1047, Issue , 2013, Pages 201-214

  Blixt, Ola ^a   Cló, Emiliano ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

Author keywords

Antibodies; Glycan binding proteins; Glycopeptides; Glycosylation; Microarrays; O glycans; Posttranslational glycosylation (PTG); Posttranslational modifications (O PTM); Specificities

Indexed keywords

GLYCOPEPTIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; GLYCOPEPTIDE MICROARRAY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN GLYCOSYLATION; PROTEIN ISOLATION; PROTEIN MICROARRAY; PROTEIN MODIFICATION; PROTEIN PURIFICATION;

AMINO ACIDS; FLUORENES; GLYCOPEPTIDES; POLYSACCHARIDES; PROTEIN ARRAY ANALYSIS; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84934437961     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-62703-544-6_14     Document Type: Article

References (37)

1. Varki A (2009) Essentials of glycobiology, 2nd edn. Cold Spring Harbor Laboratory Press, New York
2. Haltiwanger RS, Lowe JB (2004) Role of glycosylation in development. Annul Rev Biochem 73:491-537
3. Paulson JC, Blixt O, Collins BE (2006) Sweet spots in functional glycomics. Nat Chem Biol 2:238-248
4. Bennett EP, Mandel U, Clausen H et al (2011) Control of mucin-type O-glycosylation-a classification of the polypeptide GalNActransferase gene family. Glycobiology 22:736-756
5. Alvarez RA, Blixt O (2006) Identification of ligand specificities for glycan-binding proteins using glycan arrays. Methods Enzymol 415:292-310
6. Blixt O, Head S, Mondala T et al (2004) Printed covalent glycan array for ligand profi ling of diverse glycan binding proteins. Proc Natl Acad Sci U S A 101:17033-17038
7. Paulson JC, Blixt O, Collins BE (2006) Sweet spots in functional glycomics. Nat Chem Biol 2:238-248
8. Blixt O, Boos I, Mandel U (2012) In: Kosma P (ed) Anticarbohydrate antibodies. New York, Springer
9. Tarp MA, Sorensen AL, Mandel U et al (2007) Identification of a novel cancer-specific immunodominant glycopeptide epitope in the MUC1 tandem repeat. Glycobiology 17:197-209
10. Ju T, Otto VI, Cummings RD (2011) The Tn antigen-structural simplicity and biological complexity. Angew Chem Int Ed Engl 50:1770-1791
11. Clo E, Kracun SK, Nudelman AS et al (2012) Characterization of the viral O-glycopeptidome: A novel tool of relevance for vaccine design and serodiagnosis. J Virol 86:6268-6278
12. Wandall HH, Blixt O, Tarp MA et al (2010) Cancer biomarkers defi ned by autoantibody signatures to aberrant O-glycopeptide epitopes. Cancer Res 70:1306-1313
13. Blixt O, Bueti D, Burford B et al (2011) Autoantibodies to aberrantly glycosylated MUC1 in early stage breast cancer are associated with a better prognosis. Breast Canc Res 13:R25
14. Sabbatini PJ, Ragupathi G, Hood C et al (2007) Pilot study of a heptavalent vaccinekeyhole limpet hemocyanin conjugate plus QS21 in patients with epithelial ovarian, fallopian tube, or peritoneal cancer. Clin Cancer Res 13:4170-4177
15. Davis BG (2002) Synthesis of glycoproteins. Chem Rev 102:579-602
16. Schultheiss-Reimann P, Kunz H (1983) O-glycopeptide synthesis using 9- fl uorenyl methoxycarbonyl (Fmoc)-protected synthetic units. Angew Chem Int Ed Eng 22:62-63
17. Paulsen H, Schultz M, Klamann JD et al (1985) Building units of oligosaccharides. 66.Synthesis of O-glycopeptide blocks of glycophorine. Liebigs Annalen Der Chemie 2028-2048
18. Tofteng AP et al (2011) Microwave heating in solid-phase synthesis of glycopeptides. In: Dawson P, Schneider J (eds) 22nd American peptide symposium, San Diego. Pep Sci 96:512
19. Kihlberg J, Vuljanic T (1993) Piperidine is preferable to morpholine for Fmoc cleavage in solid-phase synthesis of O-linked glycopeptides. Tetrahedron Lett 34:6135-6138
20. Brocke C, Kunz H (2004) Synthetic tumorassociated glycopeptide antigens from the tandem repeat sequence of the epithelial mucin MUC4. Synthesis 525-542
21. Vuljanic T, Bergquist KE, Clausen H et al (1996) Piperidine is preferred to morpholine for Fmoc cleavage in solid phase glycopeptide synthesis as exemplified by preparation of glycopeptides related to HIV gp120 and mucins. Tetrahedron 52:7983-8000
22. Peters S, Lowary TL, Hindsgaul O et al (1995) Solid-phase synthesis of a fucosylated glycopeptide of human factor-Ix with a fucosealpha-(1-]O)-serine linkage. J Chem Soc Perkin Trans 1:3017-3022
23. Elofsson M, Salvador LA, Kihlberg J (1997) Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120. Tetrahedron 53:369-390
24. Kračun SK, Cló E, Clausen H et al (2010) Random glycopeptide bead libraries for seromic biomarker discovery. J Proteome Res 9:6705-6714
25. Hilaire P, Lowary T, Meldal M et al (1998) Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries. J Am Chem Soc 120:13312
26. Brocke C, Kunz H (2002) Synthesis of tumorassociated glycopeptide antigens. Bioorg Med Chem 10:3085-3112
27. Blixt O, Razi N (2006) Chemoenzymatic synthesis of glycan libraries. Glycobiology 415:137-153
28. Koeller KM, Wong CH (2000) Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies. Chem Rev 100:4465-4493
29. Tomizaki KY, Usui K, Mihara H (2005) Protein-detecting microarrays: Current accomplishments and requirements. ChemBioChem 6:783-799
30. Blixt O, Clo E, Nudelman AS et al (2010) A high-throughput O-glycopeptide discovery platform for seromic profi ling. J Proteome Res 9:5250-5261
31. Westerlind U, Schroder H, Hobel A et al (2009) Tumor-associated MUC1 tandem- repeat glycopeptide microarrays to evaluate serum- and monoclonal-antibody specificity. Angew Chem Int Ed Engl 121:8413-8417
32. Blixt O, Allin K, Bohorov O et al (2008) Glycan microarrays for screening sialyltransferase specificities. Glycoconj J 25:59-68
33. Tarp MA, Clausen H (2008) Mucin-type O-glycosylation and its potential use in drug and vaccine development. Biochim Biophys Acta 1780:546-563
34. Esko JD, Selleck SB (2002) Order out of chaos: Assembly of ligand binding sites in heparan sulfate. Annu Rev Biochem 71:435-471
35. Hart GW, Slawson C, Ramirez-Correa G et al (2011) Cross talk between O-GlcNAcylation and Phosphorylation: Roles in signaling, transcription, and chronic disease. Annu Rev Biochem 80:825-858
36. Hewitt JE (2011) Glycomarkers for muscular dystrophy. Biochem Soc Trans 39:336-339
37. Luther KB, Haltiwanger RS (2009) Role of unusual O-glycans in intercellular signaling. Int J Biochem Cell Biol 41:1011-1024