Solid-phase synthesis of α-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6059-6072

  Liu, Runhui ^a   Chanthamontri, Chamnongsak ^a   Han, Hongling ^a   Hernández Torres, Jesús M ^a   Wood, Karl V ^a   McLuckey, Scott A ^a   Wei, Alexander ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ETHERS; CHARACTERISTIC MASS; CHEMICAL EQUATIONS; COLLISION-INDUCED DISSOCIATION; DE-PROTECTION; ELECTRO SPRAYING; ESI-MS/MS; FRAGMENTATION PATTERNS; FREE HYDROXYL GROUPS; GLUCOSAMINE; GLUCOSAMINES; HEPARAN SULFATE; ION FRAGMENTATION; LEWIS ACIDS; PRODUCT ION SPECTRA; RAMAN ANALYSIS; REGIO-SELECTIVE; SOLID-PHASE SYNTHESIS; STRONG CORRELATIONS; SULFATE GROUPS; SULFATE IONS; TANDEM MASS SPECTROMETRY;

AROMATIC HYDROCARBONS; ASTROPHYSICS; CHEMICAL REACTIONS; CHROMATOGRAPHIC ANALYSIS; ELECTROSPRAY IONIZATION; ETHERS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; IONIZATION OF LIQUIDS; IONS; ISOMERS; LIQUID CHROMATOGRAPHY; LIQUID PHASE EPITAXY; MASS SPECTROMETERS; MASS SPECTROMETRY; ORGANIC COMPOUNDS; RESINS; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS; SULFATE MINERALS; SYNTHESIS (CHEMICAL);

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ALPHA GLUCOSAMINE; EPITOPE; GLUCOSAMINE DERIVATIVE; HEPARAN SULFATE; HYDROXYL GROUP; LEWIS ACID; RESIN; SULFATE;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CORRELATION ANALYSIS; DEPROTECTION REACTION; ELECTROSPRAY MASS SPECTROMETRY; ELIMINATION REACTION; FRAGMENTATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROMETRY; ISOMER; MASS FRAGMENTOGRAPHY; RAMAN SPECTROMETRY; SOLID PHASE SYNTHESIS; SULFONATION; TANDEM MASS SPECTROMETRY;

GLUCOSAMINE; HEPARITIN SULFATE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFURIC ACID ESTERS; TANDEM MASS SPECTROMETRY;

EID: 50149110223     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800713m     Document Type: Article

References (82)

1. Hooper, L. V.; Manzella, S. M.; Baenziger, J. U. FASEB J. 1996, 10, 1137-1146.
2. Bowman, K. G.; Bertozzi, C. R. Chem. Biol. 1999, 6, R9-R22.
3. Lubineau, A.; Bonnaffé, D. Eur. J. Org. Chem. 1999, 2523-2532.
4. Lubineau, A.; Lortat-Jacob, H.; Gavard, O.; Sarrazin, S.; Bonnaffé, D. Chem. Eur. J. 2004, 10, 4265-4282.
5. (a) Barroca, N.; Jacquinet, J.-C. Carbohydr. Res. 2002, 337, 673-689.
6. (b) Jacquinet, J.-C. Carbohydr. Res. 2004, 339, 349-359.
7. Conrad, H. E. Heparin-Binding Proteins; Academic Press: San Diego, 1998.
8. Esko, J. D.; Selleck, S. B. Annu. Rev. Biochem. 2002, 71, 435-471.
9. Mochizuki, H.; Yoshida, K.; Gotoh, M.; Sugioka, S.; Kikuchi, N.; Kwon, Y.-D.; Tawada, A.; Maeyama, K.; Inaba, N.; Hiruma, T.; Kimata, K.; Narimatsu, H. J. Biol. Chem. 2003, 278, 26780-26787.
10. Westling, C.; Lindahl, U. J. Biol. Chem. 2002, 277, 49247-49255.
11. (a) Arenberg, D. A.; Polverini, P. J.; Kunkel, S. L.; Shanafelt, A.; Strieter, R. M. In Methods in Enzymology; Horuk, R., Ed.; Academic Press: San Diego, 1997; Vol. 288, pp 190-220.
12. (b) Lever, R.; Page, C. P. Nature Rev. 2002, 1, 140-148.
13. (a) Herold, B. C.; Gerber, S. I.; Polonsky, T.; Belval, B. J.; Shaklee, P. N.; Holme, K. Virology 1995, 206, 1108-1116.
14. (b) Feyzi, E.; Trybala, E.; Bergstrom, T.; Lindahl, U.; Spillmann, D. J. Biol. Chem. 1997, 272, 24850-24857.
15. (c) Sasisekharan, R.; Schriver, Z.; Venkataraman, G.; Narayanasami, U. Nature Rev. 2002, 2, 521-528.
16. Linhardt, R. J. J. Med. Chem. 2003, 46, 2551-2564.
17. Spillmann, D.; Witt, D.; Lindahl, U. J. Biol. Chem. 1998, 273, 15487-15493.
18. (a) Venkataraman, G.; Shriver, Z.; Raman, R.; Sasisekharan, R. Science 1999, 286, 537-542.
19. (b) Reiser, N.; Venkataraman, G.; Shriver, Z.; Sasisekharan, R. Nature Med. 2001, 7, 123-128.
20. (a) Petitou, M.; van Boeckel, C. A. A. Pur. Appl. Chem. 1997, 69, 1839-1846.
21. (b) Shriver, Z.; Raman, R.; Venkataraman, G.; Drummond, K.; Turnbull, J.; Toida, T.; Linhardt, R. J.; Biemann, K.; Sasisekharan, R. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10359-10364.
22. (a) Shukla, D.; Liu, J.; Blaiklock, P.; Shworak, N. W.; Esko, J. D.; Cohen, G. H.; Eisenberg, R. J.; Rosenberg, R. D.; Spear, P. G. Cell 1999, 99, 13-22.
23. (b) Liu, J.; Shriver, Z.; Pope, R. M.; Thorp, S. C.; Duncan, M. B.; Copeland, R. J.; Raska, C. S.; Yoshida, K.; Eisenberg, R. J.; Cohen, G.; Linhardt, R. J.; Sasisekharan, R. J. Biol. Chem. 2002, 277, 33456-33467.
24. Kamimura, K.; Rhodes, J. M.; Ueda, R.; McNeely, M.; Shukla, D.; Kimata, K.; Spear, P. G.; Shworak, N. W.; Nakato, H. J. Cell Biol. 2004, 166, 1069-1079.
25. Miyamoto, K.; Asada, K.; Fukutomi, T.; Okochi, E.; Yagi, Y.; Hasegawa, T.; Asahara, T.; Sugimura, T.; Ushijima, T. Oncogene 2003, 22, 274-280.
26. Pope, R. M.; Raska, C. S.; Thorp, S. C.; Liu, J. Glycobiology 2001, 11, 505-513.
27. (a) Venkataraman, G.; Shriver, Z.; Raman, R.; Sasisekharan, R. Science 1999, 286, 537-542.
28. (b) Shriver, Z.; Raman, R.; Venkataraman, G.; Drummond, K.; Turnbull, J.; Toida, T.; Linhardt, R. J.; Biemann, K.; Sasisekharan, R. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10359-10364.
29. Tissot, B.; Gasiunas, N.; Powell, A. K.; Ahmed, Y.; Zhi, Z.-L.; Haslam, S. M.; Morris, H. R.; Turnbull, J. E.; Gallagher, J. T.; Dell, A. Glycobiology 2007, 17, 972-982.
30. (a) McLuckey, S. A. J. Am. Soc. Mass Spectrom. 1992, 3, 599-614.
31. (b) Shukla, A. K.; Futrell, J. H. J. Mass Spectrom. 2000, 35, 1069-1090.
32. Karlsson, N. G.; Karlsson, H.; Hansson, G. C. J. Mass. Spectrom. 1996, 31, 560-572.
33. (a) Saad, O. M.; Leary, J. A. Anal. Chem. 2003, 75, 2985-2995.
34. (b) Saad, O. M.; Ebel, H.; Uchimura, K.; Rosen, S. D.; Bertozzi, C. R.; Leary, J. A. Glycobiology 2005, 15, 818-826.
35. Zaia, J.; Costello, C. E. Anal. Chem. 2003, 75, 2445-2455.
36. Minamisawa, T.; Hirabayashi, J. Rapid Commun. Mass Spectrom. 2005, 19, 1788-1796.
37. (a) Wolff, J. J.; Laremore, T. N.; Busch, A. M.; Linhardt, R. J.; Amster, I. J. J. Am. Soc. Mass Spectrom. 2008, 19, 294-304.
38. (b) Wolff, J. J.; Amster, I. J.; Chi, L. L.; Linhardt, R. J. J. Am. Soc. Mass Spectrom. 2007, 18, 234-244.
39. (c) Wolff, J. J.; Chi, L. L.; Linhardt, R. J.; Amster, I. J. Anal. Chem. 2007, 79, 2015-2022.
40. Gunay, N. S.; Tadano-Aritomi, K.; Toida, T.; Ishizuka, I.; Linhardt, R. J. Anal. Chem. 2003, 75, 3226-3231.
41. Tissot, B.; Salpin, J.-Y.; Martinez, M.; Gaigeot, M.-P.; Daniel, R. Carbohydr. Res. 2006, 341, 598-609.
42. (a) Bruehl, R. E.; Bertozzi, C. R.; Rosen, S. D. J. Biol. Chem. 2000, 275, 32642-32648.
43. (b) Hemmerich, S.; Rosen, S. D. Glycobiology 2000, 10, 849-856.
44. Seeberger, P. H.; Haase, W. C. Chem. Rev. 2000, 100, 4349-4393.
45. (a) Zhu, T.; Boons, G. J. Tetrahedron: Asymmetry 2000, 11, 199-205.
46. (b) Tanaka, H.; Ishida, T.; Matoba, N.; Tsukamoto, H.; Yamada, H.; Takahashi, T. Angew. Chem., Int. Ed. 2006, 45, 6349-6352.
47. Solid-phase supports have been used in the synthesis of sulfated peptides: (a) Kitagawa, K.; Aida, C.; Fujiwara, H.; Yagami, T.; Futaki, S.; Kogire, M.; Ida, J.; Inoue, K. J. Org. Chem. 2001, 66, 1-10.
48. (b) Ueki, M.; Watanabe, S.; Ishii, Y.; Okunaka, O.; Uchino, K.; Saitoh, T.; Higashi, K.; Nakashima, H.; Yamamoto. N.; Ogawara, H. Bioorg. Med. Chem. 2001, 9, 477-486.
49. (c) Campos, S. V.; Miranda, L. P.; Meldal, M. J. Chem. Soc., Perkin Trans. 1 2002, 682-86.
50. (d) Young, T.; Kiessling, L. L. Angew. Chem., Int. Ed. 2002, 41, 3449-3451.
51. (a) Hernández-Torres, J. M.; Liew, S.-T.; Achkar, J.; Wei, A. Synthesis 2002, 487-490.
52. (b) Liew, S.-T.; Wei, A. Carbohydr. Res. 2002, 337, 1319-1324.
53. Fan, R. H.; Achkar, M.; Hernandez-Torres, J. M.; Wei, A. Org. Lett. 2005, 7, 5095-5098.
54. Other selected examples of carbohydrates with orthogonally protecting group systems: (a) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138.
55. (b) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. 1998, 37, 2503-2505.
56. (c) Prabhu, A.; Venot, A.; Boons, G.-J. Org. Lett. 2003, 5, 4975-4978.
57. (d) Haller, M. F.; Boons, G.-J. Eur. J. Org. Chem. 2002, 2033-2038.
58. (e) Misra, A. K.; Agnihotri, G.; Madhusudan, S. K.; Tiwari, P. J. Carbohydr. Chem. 2004, 23, 191-199.
59. Alper, P. B.; Hung, S. C.; Wong, C. H. Tetrahedron Lett. 1996, 37, 6029-6032.
60. Pozsgay, V.; Glaudemans, C. P. J.; Robbins, J. B.; Schneerson, R. Tetrahedron 1992, 48, 10249-10264.
61. Hernández-Torres, J. M.; Achkar, J.; Wei, A. J. Org. Chem. 2004, 69, 7206-7211.
62. Glycosylation using an α-thioethyl derivative with a 4-O-p-methoxybenzyl ether afforded a 9:1 α/β ratio in 90% combined yield. Hernández-Torres, J. M. Ph.D. Thesis, Purdue University, 2005.
63. (a) Paulsen, H.; Stenzel, W. Angew. Chem., Int. Ed. 1975, 14, 558.
64. (b) van Straten, N. C. R.; Kriek, N. M. A. J.; Cziria, Z. A. C.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1997, 53, 6539-6554.
65. Lohman, G. J. S.; Seeberger, P. H. J. Org. Chem. 2004, 69, 4081-4093.
66. Cid, M. B.; Alfonso, F.; Martín-Lomas, M. Chem. Eur. J. 2006, 11, 928-938.
67. -1 in Figure 2a is unknown.
68. Noti, C.; de Paz, J. L.; Polito, L.; Seeberger, P. H. Chem. Eur. J. 2006, 12, 8664-8686.
69. (a) Liu, Y.; Lien, I. F. F.; Ruttgaizer, S.; Dove, P.; Taylor, S. D. Org. Lett. 2004, 6, 209-212.
70. (b) Gunnarsson, G. T.; Riaz, M.; Adams, J.; Desai, U. R. Bioorg. Med. Chem. 2005, 13, 1783-1789.
71. (c) Simpson, L. S.; Widlanski, T. S. J. Am. Chem. Soc. 2006, 128, 1605-1610.
72. (d) Ingram, L. J.; Taylor, S. D. Angew. Chem., Int. Ed. 2006, 45, 3503-3506.
73. Kaburagi, Y.; Kishi, Y. Org. Lett. 2007, 9, 723-726.
74. It should be noted that differences in the mass analyzers and CID conditions used in this study had a significant impact on their respective ESI-MS/MS spectra. In particular, preliminary MS/MS analyses using the ion trap mass analyzer were performed with a cutoff at 30% of the parent ion m/z ratio; therefore, no ions below this threshold could be observed.
75. Domon, B.; Costello, C. E. Glycoconjugate J. 1988, 5, 397-409.
76. 4N salts suggest that the counterion does not have a significant effect on the negative-mode ESI-MS/MS spectra.
77. Isotopic parent ion peaks were observed in the MS/MS spectra of 4b, 7b, and 6b. These were higher than expected after CID, possibly due to perturbations in rf resonance frequencies corresponding with the expected parent ions.
78. Robins, M. J.; Nowak, I.; Wnuk, S. F.; Hansske, F.; Madej, D. J. Org. Chem. 2007, 72, 8216-8221.
79. (a) Wit, G. D.; Kieboom, A. P. G.; Bekkum, H. V. Carbohydr. Res. 1979, 74, 157-175.
80. (b) Calle, P.; Sanchez, A.; Sieiro, C. J. Chem. Soc., Perkin Trans. 2 1990, 1181-1185.
81. Shevchenko, A.; Chernushevich, I.; Ens, W.; Standing, K. G.; Thomson, B.; Wilm, M.; Mann, M. Rapid Commun. Mass Spectrom. 1997, 11, 1015-1024.
82. Wells, J. M.; Chrisman, P. A.; McLuckey, S. A. J. Am. Soc. Mass Spectrom. 2002, 13, 614-622.