Stability of 5(6)-carboxyfluorescein in microwave-assisted synthesis of fluorescein-labelled O-dimannosylated peptides

Synthesis

Volumn , Issue 13, 2009, Pages 2210-2222

  Kowalczyk, Renata ^a   Harris, Paul W R ^a   Dunbar, Rod P ^a,b   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Carbohydrates; Glycopeptides; Glycosylations; Mannosylated amino acids; Solid phase synthesis

Indexed keywords

AMINO GROUP; AUTOMATED SYNTHESIS; BIOLOGICAL EVALUATION; BUILDING BLOCK; CARBOXYFLUORESCEIN; GLYCOPEPTIDE SYNTHESIS; GLYCOPEPTIDES; GLYCOSYLATIONS; MANNOSYLATED AMINO ACIDS; MICROWAVE ASSISTED SYNTHESIS; MICROWAVE CONDITIONS; MICROWAVE-ASSISTED; SOLID-PHASE SYNTHESIS;

AMINATION; AMINES; AMINO ACIDS; CARBOHYDRATES; DYES; LABELS; MICROWAVES; ORGANIC ACIDS; POLYETHYLENE GLYCOLS; RESINS;

PEPTIDES;

12 [[2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZOYL ALPHA DEXTRO MANNOPYRANOSYL) ALPHA DEXTRO MANNOPYRANOSYL]OXY] 4,7,10 TRIOXADODECANOIC ACID; 2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZOYL ALPHA DEXTRO MANNOPYRANOSYL) ALPHA DEXTRO MANNOPYRANOSIDE; 4 METHYLPHENYL 2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZOYL ALPHA DEXTRO MANNOPYRANOSYL) 1 THIO ALPHA DEXTRO MANNOPYRANOSIDE; 6 CARBOXYFLUORESCEIN; MANNOSIDE; N (9 FLUORENYLMETHOXYCARBONYL) O [2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZOYL ALPHA DEXTRO MANNOPYRANOSYL) ALPHA DEXTRO MANNOPYRANOSYL] 1 SERINE ALLYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; FLUORESCENCE; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; MICROWAVE RADIATION; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID;

EID: 67651124603     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216820     Document Type: Article

References (68)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683.
2. Powell, M. F.; Grey, H.; Gaeta, F.; Sette, A.; Colon, S. J. Pharm. Sci. 1992, 81, 731.
3. Figdor, C. G.; van Kooyk, Y.; Adema, G. J. Nat. Rev. Immunol. 2002, 2, 77.
4. Sheng, K. C.; Pouniotis, D. S.; Wright, M. D.; Tang, C. K.; Lazoura, E.; Pietersz, G. A.; Apostolopoulos, V. Immunology 2006, 118, 372.
5. Sheng, K. C.; Kalkanidis, M.; Pouniotis, D. S.; Esparon, S.; Tang, C. K.; Apostolopoulos, V.; Pietersz, A. Eur. J. Immunol. 2008, 38, 424.
6. (a) Drickamer, K. Nat. Struct. Biol. 1995, 2, 437.
7. (b) Crocker, P. R.; Feizi, T. Curr. Opin. Struct. Biol. 1996, 6, 679.
8. (c) Frison, N.; Taylor, M. E.; Soilleux, E.; Bousser, R.; Mayer, M. T.; Monsigny, M.; Drickamer, K.; Roche, A. C. J. Biol. Chem. 2003, 278, 23922.
9. (a) Biessen, E. A. L.; Noorman, F.; van Teijlingen, M. E.; Kuiper, J.; Barrett-Bergshoeff, M.; Bijsterbosch, M. K.; Rijken, D. C.; van Berkel, T. J. C. J. Biol. Chem. 1996, 271, 28024.
10. (b) Angyalosi, G.; Grandjean, C.; Lamirand, M.; Auriault, C.; Gras-Masse, H.; Melnyk, O. Bioorg. Med. Chem. Lett. 2002, 12, 2723.
11. (a) Hamdaoui, B.; Dewynter, G.; Capony, F.; Montero, J. L.; Toiron, C.; Hnach, M.; Rochefort, H. Bull. Soc. Chim. Fr. 1994, 131, 854.
12. (b) Free, P. Org. Biomol. Chem. 2006, 4, 1817.
13. Geijtenbeek, T. B. H.; van Vliet, S. J.; Engering, A.; 't Hart, B. A.; van Kooyk, Y. Annu. Rev. Immunol. 2004, 22, 33.
14. Willment, J. A.; Brown, G. D. Trends Microbiol. 2008, 16, 27.
15. Brimble, M. A.; Kowalczyk, R.; Harris, P. W. R.; Dunbar, P. R.; Muir, V. J. Org. Biomol. Chem. 2008, 6, 112.
16. Gamblin, D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2009, 109, 131.
17. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
18. (b) Lavielle, S.; Ling, N. C.; Guillemin, R. C. Carbohydr. Res. 1981, 89, 221.
19. (c) Haase, C.; Seitz, O. In Glycopeptides and Glycoproteins: Synthesis, Structure, and Application, Vol. 267; Wittmann, V., Ed.; Springer: Berlin, 2007, 1.
20. (a) Hollósi, M.; Kollát, E.; Laczkó, I.; Medzihradszky, K. F.; Thurin, J.; Otvös, L. Jr. Tetrahedron Lett. 1991, 32, 1531.
21. (b) Paulsen, H.; Schleyer, A.; Mathieux, N.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1997, 281.
22. (c) Andrews, D. M.; Seale, P. W. Int. J. Pept. Protein Res. 1993, 42, 165.
23. Kent, S. B. H. Ann. Rev. Biochem. 1988, 57, 957.
24. (a) Yu, H. M.; Chen, S. T.; Wang, K. T. J. Org. Chem. 1992, 57, 4781.
25. (b) Erdelyi, M.; Gogoll, A. Synthesis 2002, 1592.
26. (c) Campiglia, P.; Gomez-Monterrey, I.; Longobardo, L.; Lama, T.; Novellino, E.; Grieco, P. Tetrahedron Lett. 2004, 45, 1453.
27. (d) Murray, J. K.; Gellman, S. H. Org. Lett. 2005, 7, 1517.
28. (e) Murray, J. K.; Farooqi, B.; Sadowsky, J. D.; Scalf, M.; Freund, W. A.; Smith, L. M.; Chen, J.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13271.
29. (a) Matsushita, T.; Hinou, H.; Fumoto, M.; Kurogochi, M.; Fujitani, N.; Shimizu, H.; Nishimura, S. I. J. Org. Chem. 2006, 71, 3051.
30. (b) Matsushita, T.; Hinou, H.; Kurogochi, M.; Shimizu, H.; Nishimura, S. I. Org. Lett. 2005, 7, 877.
31. Fara, M. A.; Diaz-Mochon, J. J.; Bradley, M. Tetrahedron Lett. 2006, 47, 1011.
32. Katritzky, A. R.; Yoshioka, M.; Narindoshvili, T.; Chung, A.; Johnson, J. V. Org. Biomol. Chem. 2008, 6, 4582.
33. (a) Roy, R.; Saha, U. K. Chem. Commun. 1996, 201.
34. (b) Boumrah, D.; Campbell, M. M.; Fenner, S.; Kinsman, R. G. Tetrahedron 1997, 53, 6977.
35. Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215.
36. (a) Boumrah, D.; Campbell, M. M.; Fenner, S.; Kinsman, R. G. Tetrahedron Lett. 1991, 32, 7735.
37. (b) Boullanger, P.; Sancho-Camborieux, M. R.; Bouchu, M. N.; Marron-Brignone, L.; Morelis, R. M.; Coulet, P. R. Chem. Phys. Lipids 1997, 90, 63.
38. (c) Bhattacharya, S.; Dileep, P. V. Tetrahedron Lett. 1999, 40, 8167.
39. Schmidt, M.; Dobner, B.; Nuhn, P. Eur. J. Org. Chem. 2002, 669.
40. Kunz, H.; Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 1697.
41. Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043.
42. Franzyk, H.; Meldal, M.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1995, 2883.
43. Koenigs, W.; Knörr, E. Chem. Ber. 1901, 34, 957.
44. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056.
45. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
46. Zhu, Y.; Kong, F. Carbohydr. Res. 2001, 332, 1.
47. Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
48. Zhang, Z.; Ollmann, I. R.; Ye, X. S.; Wischnat, R.; Baasov, T.; Wong, C. H. J. Am. Chem. Soc. 1999, 121, 734.
49. Tai, C. A.; Kulkarni, S. S.; Hung, S. C. J. Org. Chem. 2003, 68, 8719.
50. (a) Mukhopadhyay, B.; Kartha, K. P. R.; Russell, D. A.; Field, R. A. J. Org. Chem. 2004, 69, 7758.
51. (b) Agnihotri, G.; Tiwari, P.; Misra, A. K. Carbohydr. Res. 2005, 340, 1393.
52. (c) Dasgupta, S.; Rajput, V. K.; Roy, B.; Mukhopadhyay, B. J. Carbohydr. Chem. 2007, 26, 91.
53. Zemplén, G.; Pascu, E. Chem. Ber. 1929, 62, 1613.
54. Kocieński, P. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2005.
55. (a) Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731.
56. (b) Schmidt, R. R.; Grundler, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 781.
57. Tvaroska, I.; Taravel, F. R. Adv. Carbohydr. Chem. Biochem. 1995, 51, 15.
58. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
59. Dessolin, M.; Guillerez, M. G.; Thieriet, N.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741.
60. Seitz, O.; Kunz, H. J. Org. Chem. 1997, 62, 813.
61. Fischer, R.; Mader, O.; Jung, G.; Brock, R. Bioconjugate Chem. 2003, 14, 653.
62. Kaiser, E.; Colescot, R. I.; Bossinge, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
63. Rapp, W. In Combinatorial Peptide and Nonpeptide Libraries: A Handbook; Jung, G., Ed.; VCH: Weinheim, 1996, 425.
64. Delgado, M.; Janda, K. D. Curr. Org. Chem. 2002, 6, 1031.
65. Kempe, M.; Barany, G. J. Am. Chem. Soc. 1996, 118, 7083.
66. Camperi, S. A.; Marani, M. M.; Iannucci, N. B.; Cote, S.; Albericio, F.; Cascone, O. Tetrahedron Lett. 2005, 46, 1561.
67. Watt, J. A.; Williams, S. J. Org. Biomol. Chem. 2005, 3, 1982.
68. Saksena, R.; Zhang, J.; Kováč, P. J. Carbohydr. Chem. 2002, 21, 453.