請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/96327
標題: Chapter 1. Mild and Highly α-Selective O-Sialylation Method Based on Pre-activation: Access to Gangliosides Hp-s1, DSG-A, and their Analogues. Chapter 2. Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine glycopeptide.
第一章. 基於預活化的溫和且高-選擇性的O-唾液酸化法: 獲取神經節苷脂 Hp-s1, DSG-A及它們的衍生物. 第二章. β(1→4)鏈結的三醣及四醣葡萄糖胺醣胜肽的反覆合成.
作者: Ganesh Shelke
迦納辛
關鍵字: 唾液酸化法
葡萄糖胺醣胜肽
神經節苷脂
gangliosides
Hp-S1
DSG-A
glycoproteins
引用: References 1. Varki, A.; Cummings, R. D.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Marth, J. D.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E. Proteomics 2009, 9, 5398. 2. (a) Severi, E.; Hood, D.; Thomas, G. Sialic acid utilization by bacterial pathogens. Microbiology 153 (Pt 9): 2817-2822. doi: 10.1099/mic; 0.2007/009480-0 PubMed CrossRef Google Scholar: 2007; (b) Vimr, E. R.; Kalivoda, K. A.; Deszo, E. L.; Steenbergen, S. M. Microbiol. Mol. Biol. Rev. 2004, 68, 132. 3. Schauer, R. Methods Enzymol. 1978, 50, 64. 4. Warren, L., Bound carbohydrates in nature. Cambridge University Press: 1994. 5. Wang, B.; Brand-Miller, J. Eur. J. Clin. Nutr. 2003, 57, 1351. 6. Schauer, R.; Kelm, S.; Reuter, G.; Roggentin, P.; Shaw, L., Biochemistry and role of sialic acids. In Biology of the sialic acids, Springer: 1995; pp 7. 7. Severi, E.; Hood, D. W.; Thomas, G. H. Microbiology 2007, 153, 2817. 8. (a) Kolter, T. ISRN Biochemistry 2012, 2012, 36; (b) Kolter, T. ISRN biochemistry 2012, 2012. 9. Kaneko, M.; Yamada, K.; Miyamoto, T.; Inagaki, M.; Higuchi, R. Chem. Pharm. Bull. 2007, 55, 462. 10. (a) Hakomori, S. -I.; Igarashi, Y. Iran. J. Immunol. 1995, 118, 1091; (b) Lopez, P. H.; Schnaar, R. L. Curr. Opin. Struct. Biol. 2009, 19, 549. 11. Simon, B.; Malisan, F.; Testi, R.; Nicotera, P.; Leist, M. Cell Death Differ. 2002, 9, 758. 12. (a) Kusunoki, S.; Kaida, K. -I.; Ueda, M. Biochim. Biophys. Acta, Gen. Subj. 2008, 1780, 441; (b) Zhang, H. -L.; Gao, S. -J.; Yang, Y.; Wu, J. Iran. J. Immunol. 2010, 7, 198; (c) Ilyas, A.; Willison, H.; Quarles, R.; Jungalwala, F.; Cornblath, D.; Trapp, B.; Griffin, D.; Griffin, J.; McKhann, G. Ann. Neurol. 1988, 23, 440. 13. Robert, K. Y.; Tsai, Y.-T.; Ariga, T. Neurochem. Res. 2012, 37, 1230. 14. Nojiri, H.; Stroud, M.; Hakomori, S.-I. J. Biol. Chem. 1991, 266, 4531. 15. Yamashita, T.; Wada, R.; Sasaki, T.; Deng, C.; Bierfreund, U.; Sandhoff, K.; Proia, R. L. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 9142. 68 16. Hakomori, S.-I. Cancer Res. 1996, 56, 5309. 17. (a) Taube, S.; Jiang, M.; Wobus, C. E. Viruses 2010, 2, 1011; (b) Isa, P.; Gutiérrez, M.; Arias, C. F.; López, S. 2008; (c) Isa, P.; Arias, C. F.; López, S. Glycoconjugate J. 2006, 23, 27. 18. (a) Varki, A. Nature 2007, 446, 1023; (b) Rosenberg, A., Biological roles of sialic acid. Springer Science & Business Media: 2013. 19. Nobile-Orazio, E.; Carpo, M.; Scarlato, G. Drugs 1994, 47, 576. 20. Tsuji, S.; Yamashita, T.; Nagai, Y. Iran. J. Immunol. 1988, 104, 498. 21. Tsuji, S.; Arita, M.; Nagai, Y. Iran. J. Immunol. 1983, 94, 303. 22. Prinetti, A.; Iwabuchi, K.; Hakomori, S.-i. J. Biol. Chem. 1999, 274, 20916. 23. AGNATI, L. F.; FUXE, K.; CALZA, L.; BENFENATI, F.; CAVICCHIOLI, L.; TOFFANO, G.; GOLDSTEIN, M. Acta Physiologica 1983, 119, 347. 24. Barrier, S. C. Science 1992, 256, 843. 25. Argentino, C.; Sacchetti, M.; Toni, D.; Savoini, G.; D'arcangelo, E.; Erminio, F.; Federico, F.; Milone, F. F.; Gallai, V.; Gambi, D. Stroke 1989, 20, 1143. 26. Higuchi, R.; Inagaki, M.; Yamada, K.; Miyamoto, T. Journal of Natural Medicines 2007, 61, 367. 27. Higuchi, R.; Inukai, K.; Jhou, J.; Honda, M.; Komori, T.; Tsuji, S.; Nagai, Y. Liebigs Ann Chem 1993, 359. 28. Yamada, K.; Tanabe, K.; Miyamoto, T.; Kusumoto, T.; Inagaki, M.; Higuchi, R. Chem. Pharm. Bull. 2008, 56, 734. 29. Ijuin, T.; Kitajima, K.; Song, Y.; Kitazume, S.; Inoue, S.; Haslam, S. M.; Morris, H. R.; Dell, A.; Inoue, Y. Glycoconjugate J. 1996, 13, 401. 30. Tsai, Y.-F.; Shih, C.-H.; Su, Y.-T.; Yao, C.-H.; Lian, J.-F.; Liao, C.-C.; Hsia, C.-W.; Shui, H.-A.; Rani, R. Org. Biomol. Chem. 2012, 10, 931. 31. (a) Chen, W.-S.; Sawant, R. C.; Yang, S. -A.; Liao, Y. -J.; Liao, J. -W.; Badsara, S. S.; Luo, S. -Y. RSC Adv. 2014, 4, 47752; (b) Hung, J. -T.; Yeh, C. -H.; Yang, S. - A.; Lin, C. -Y.; Tai, H. -J.; Shelke, G. B.; Reddy, D. M.; Yu, A. L.; Luo, S.-Y. ACS Chem. Neurosci. 2016, 7, 1107. 32. (a) Hsu, C. H.; Chu, K. C.; Lin, Y. S.; Han, J. L.; Peng, Y. S.; Ren, C. T.; Wu, C. Y.; Wong, C. H. Chem. Eur. J. 2010, 16, 1754; (b) Okamoto, K.; Goto, T. Tetrahedron 1990, 46, 5835; (c) Liu, Y.; Ruan, X.; Li, X.; Li, Y. J. Org. Chem. 2008, 73, 4287. 69 33. (a) Paulsen, H.; Tietz, H. Angew. Chem., Int. Ed. 1982, 21, 927; (b) Paulsen, H.; Tietz, H. Carbohydr. Res. 1984, 125, 47. 34. (a) Kondo, H.; Ichikawa, Y.; Wong, C. H. J. Am. Chem. Soc. 1992, 114, 8748; (b) Martin, T. J. Tetrahedron Lett. 1992, 33, 6123. 35. Haberman, J. M.; Gin, D. Y. Org. Lett. 2003, 5, 2539. 36. Tanaka, H.; Nishiura, Y.; Takahashi, T. J. Am. Chem. Soc. 2006, 128, 7124. 37. (a) Crich, D.; Li, W. J. Org. Chem. 2007, 72, 2387; (b) Crich, D.; Li, W. J. Org. Chem. 2007, 72, 7794. 38. Lu, Y.-S.; Li, Q.; Zhang, L.-H.; Ye, X.-S. Org. Lett. 2008, 10, 3445. 39. Huang, X.; Huang, L.; Wang, H.; Ye, X. S. Angew. Chem. 2004, 116, 5333. 40. Sun, B.; Jiang, H. Tetrahedron Lett. 2011, 52, 6035. 41. Fügedi, P.; Garegg, P. J. Carbohydr. Res. 1986, 149, C9. 42. Yuan, X. Synthesis of carbon-linked neuraminic acid oligomers as potential immunogen for meningococcal meningitis and carcinomas. Rensselaer Polytechnic Institute, 2007. 43. Dasgupta, F.; Garegg, P. J. Carbohydr. Res. 1988, 177, c13. 44. Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702. 45. Wu, Y. -F.; Tsai, Y. -F.; Guo, J. -R.; Yu, C. -P.; Yu, H. -M.; Liao, C. -C. Org. Biomol. Chem. 2014, 12, 9345. 46. Harris, B. N.; Patel, P. P.; Gobble, C. P.; Stark, M. J.; De Meo, C. Eur. J. Org. Chem. 2011, 2011, 4023. 47. Wu, Y. -F.; Tsai, Y. -F. Org. Lett. 2017, 19, 4171−4174. 48. Ando, H.; Koike, Y.; Koizumi, S.; Ishida, H.; Kiso, M. Angew. Chem., Int. Ed. 2005, 44, 6759. 49. Ando, H.; Koike, Y.; Ishida, H.; Kiso, M. Tetrahedron Lett. 2003, 44, 6883. 50. Gong, J.; Liu, H.; Nicholls, J. M.; Li, X. Carbohydr. Res. 2012, 361, 91. 51. Uchinashi, Y.; Tanaka, K.; Manabe, Y.; Fujimoto, Y.; Fukase, K. Journal of Carbohydrate Chemistry 2014, 33, 55. 52. Shelke, G. B.; Chen, B.-R.; Yang, S. -A.; Kuo, T. -M.; Syu, Y. -L.; Ko, Y. -C.; Luo, S. -Y. Asian J. Org. Chem., 2016, DOI: 10.1002/ajoc.201700358. 53. (a) Lin, C. -C.; Lin, N. -P.; Sahabuddin, L. S.; Reddy, V. R.; Huang, L.-D.; Hwang, K. C.; Lin, C.-C. J. Org. Chem. 2010, 75, 4921; (b) Liang, F.-f.; Chen, L.; Xing, G.- 70 w. Synlett 2009, 2009, 425; (c) Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273. 54. Verma, V. P.; Wang, C. C. Chem. Eur. J. 2013, 19, 846. 55. Ye, X.-S.; Huang, X.; Wong, C.-H. Chem. Commun. 2001, 974. 56. Yu, C. S.; Niikura, K.; Lin, C. C.; Wong, C. H. Angew. Chem., Int. Ed. 2001, 40, 2900. 57. Zhang, X.-T.; Gu, Z.-Y.; Xing, G.-W. Carbohydr. Res. 2014, 388, 1. 58. Kumar, P. S.; Banerjee, A.; Baskaran, S. Angew. Chem., Int. Ed. 2010, 49, 804. 59. Diaz, Y. R. G.; Wojno, J.; Cox, L. R.; Besra, G. S. Tetrahedron: Asymmetry 2009, 20, 747. 60. Baek, J. Y.; Lee, B.-Y.; Jo, M. G.; Kim, K. S. J. Am. Chem. Soc. 2009, 131, 17705. 61. Sawant, R. C.; Hung, J. T.; Chuang, H. L.; Lin, H. S.; Chen, W. S.; Yu, A. L.; Luo, S. Y. Eur. J. Org. Chem. 2013, 2013, 7611. 62. Martín-Santamaría, S.; André, S.; Buzamet, E.; Caraballo, R.; Fernández-Cureses, G.; Morando, M.; Ribeiro, J. P.; Ramírez-Gualito, K.; de Pascual-Teresa, B.; Menéndez, M. Org. Biomol. Chem. 2011, 9, 5445. 63. (a) Zhang, H.; Gao, Y.; Zhao, F.-L.; Qiao, P.-F.; Yan, Y. Cell. Mol. Neurobiol. 2015, 35, 265; (b) Meng, P.; Yoshida, H.; Matsumiya, T.; Imaizumi, T.; Tanji, K.; Xing, F.; Hayakari, R.; Dempoya, J.; Tatsuta, T.; Aizawa-Yashiro, T. Neurosci. Res. 2013, 75, 94. 64. Röder, P. V.; Wu, B.; Liu, Y.; Han, W. Exp. Mol. Med. 2016, 48, e219. 65. Council, N. R., Transforming glycoscience: a roadmap for the future. National Academies Press: 2012. 66. Johansen, P. G.; Marshall, R.; Neuberger, A. Biochem. J. 1961, 78, 518. 67. Talbot, P.; Shur, B. D.; Myles, D. G. Biol. Reprod. 2003, 68, 1. 68. Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370. 69. Varki, A. Glycobiology 1993, 3, 97. 70. Maverakis, E.; Kim, K.; Shimoda, M.; Gershwin, M. E.; Patel, F.; Wilken, R.; Raychaudhuri, S.; Ruhaak, L. R.; Lebrilla, C. B. J. Autoimmun. 2015, 57, 1. 71. Witte, K.; Sears, P.; Martin, R.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 2114. 72. Hojo, H.; Nakahara, Y. Pept. Sci. 2007, 88, 308. 71 73. Montreuil, J. Adv. Carbohydr. Chem. Biochem. 1980, 37, 157. 74. Teng-umnuay, P.; Morris, H. R.; Dell, A.; Panico, M.; Paxton, T.; West, C. M. J. Biol. Chem. 1998, 273, 18242. 75. de Beer, T.; Vliegenthart, J. F.; Loeffler, A.; Hofsteenge, J. Biochemistry 1995, 34, 11785. 76. Haynes, P. A. Glycobiology 1998, 8, 1. 77. Pierce, S. K.; Maugel, T. K.; Reid, L., Illustrated invertebrate anatomy. Oxford University Press: 1987. 78. Tang, W. J.; Fernandez, J. G.; Sohn, J. J.; Amemiya, C. T. Curr. Biol. 2015, 25, 897. 79. Kono, H. Biopolymers 2004, 75, 255. 80. Crini, G.; Badot, P. -M. Progress in Polymer Science 2008, 33, 399. 81. Jayakumar, R.; Prabaharan, M.; Kumar, P. S.; Nair, S.; Tamura, H. Biotechnol. Adv. 2011, 29, 322. 82. Nagahama, H.; Kashiki, T.; Nwe, N.; Jayakumar, R.; Furuike, T.; Tamura, H. Carbohydr. Polym. 2008, 73, 456. 83. Jayakumar, R.; Rani, V. D.; Shalumon, K.; Kumar, P. S.; Nair, S.; Furuike, T.; Tamura, H. Int. J. Biol. Macromol. 2009, 45, 260. 84. Shalumon, K.; Binulal, N.; Selvamurugan, N.; Nair, S.; Menon, D.; Furuike, T.; Tamura, H.; Jayakumar, R. Carbohydr. Polym. 2009, 77, 863. 85. Yusof, N. L. B. M.; Lim, L. Y.; Khor, E. J. Biomed. Mater. Res., Part A 2001, 54, 59. 86. Prabaharan, M.; Mano, J. Drug delivery 2004, 12, 41. 87. Brown, M. A.; Daya, M. R.; Worley, J. A. J. Emerg. Med. 2009, 37, 1. 88. Tashiro, T. Macromol. Mater. Eng. 2001, 286, 63. 89. Sietsma, J. H.; Din, A. B.; Ziv, V.; Sjollema, K. A.; Yarden, O. Microbiology 1996, 142, 1591. 90. Kumar, M. N. R. React. Funct. Polym. 2000, 46, 1. 91. Shi, X.; Fang, Q.; Ding, M.; Wu, J.; Ye, F.; Lv, Z.; Jin, J. J. Biomater. Appl. 2016, 30, 1092. 92. TOKORO, A.; TAKEWAKI, N.; Suzuki, K.; MIKAMI, T.; SUZUKI, S.; SUZUKI, M. Chem. Pharm. Bull. 1988, 36, 784. 72 93. Mills, K. H.; Cosgrove, C.; McNeela, E. A.; Sexton, A.; Giemza, R.; Jabbal-Gill, I.; Church, A.; Lin, W.; Illum, L.; Podda, A. Infect. Immun. 2003, 71, 726. 94. Phillips, I. Int. J. Antimicrob. Agents 2007, 30, 101. 95. Levine, D. P. Clin. Infect. Dis. 2006, 42, S5. 96. Norden, C.; Niederreiter, K.; Shinners, E. M. Infection 1986, 14, 136. 97. Malabarba, A.; Nicas, T. I.; Thompson, R. C. Med. Res. Rev. 1997, 17, 69. 98. Howden, B. P.; Davies, J. K.; Johnson, P. D.; Stinear, T. P.; Grayson, M. L. Clin. Microbiol. Rev. 2010, 23, 99. 99. Tsao, N.; Wang, C.-H.; Her, L. -J.; Tzen, K. -Y.; Chen, J.-Y.; Yu, D.-F.; Yang, D. J. BioMed Res. Int. 2011, 2011. 100. Strovel, J.; Sittampalam, S.; Coussens, N. P.; Hughes, M.; Inglese, J.; Kurtz, A.; Andalibi, A.; Patton, L.; Austin, C.; Baltezor, M. 2016. 101. Wei, I.-C.; Tsao, N.; Huang, Y.-H.; Ho, Y.-S.; Wu, C.-C.; Yu, D.-F.; Yang, D. J. Appl. Radiat. Isot. 2008, 66, 320. 102. Tansey, W.; Ke, S.; Cao, X.-Y.; Pasuelo, M. J.; Wallace, S.; Li, C. J. Controlled Release 2004, 94, 39. 103. Bernkop-Schnürch, A.; Hornof, M.; Guggi, D. Eur. J. Pharm. Biopharm. 2004, 57, 9. 104. Halkes, K. M.; Gotfredsen, C. H.; Grøtli, M.; Miranda, L. P.; Duus, J. Ø.; Meldal, M. Chem. Eur. J. 2001, 7, 3584. 105. Maljaars, C. E. P.; Halkes, K. M.; de Oude, W. L.; Haseley, S. R.; Upton, P. J.; McDonnell, M. B.; Kamerling, J. P. J. Comb. Chem. 2006, 8, 812. 106. Tejera, S.; Dorta, R. L.; Vázquez, J. T. Tetrahedron: Asymmetry 2016, 27, 896. 107. Lin, C. H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C. H. J. Am. Chem. Soc. 1992, 114, 10138. 108. Chen, M.; Huang, C.; He, C.; Zhu, W.; Xu, Y.; Lu, Y. Chem. Commun. 2012, 48, 9522. 109. Macchione, G.; de Paz, J. L.; Nieto, P. M. Carbohydr. Res. 2014, 394, 17. 110. Bianchi, A.; Bernardi, A. J. Org. Chem. 2006, 71, 4565. 111. Lukin, O.; Gramlich, V.; Kandre, R.; Zhun, I.; Felder, T.; Schalley, C. A.; Dolgonos, G. J. Am. Chem. Soc. 2006, 128, 8964. 73 112. Chen, W. A.; Mautino, M. R.; Martin, B., Carbohydrate-modified glycoproteins and uses thereof. Google Patents: 2014. 113. Grann Hansen, S.; Skrydstrup, T. Eur. J. Org. Chem. 2007, 2007, 3392. 114. Sadeghi-Khomami, A.; Forcada, T. J.; Wilson, C.; Sanders, D. A.; Thomas, N. R. Org. Biomol. Chem. 2010, 8, 1596. 115. Sarkar, V.; Mukhopadhyay, B. Carbohydr. Res. 2015, 406, 65. 116. Orgueira, H. A.; Bartolozzi, A.; Schell, P.; Litjens, R. E.; Palmacci, E. R.; Seeberger, P. H. Chem. Eur. J. 2003, 9, 140. 117. Lewicky, J. D.; Ulanova, M.; Jiang, Z.-H. Carbohydr. Res. 2011, 346, 1705. 118. Manabe, S.; Ishii, K.; Satoh, H.; Ito, Y. Tetrahedron 2011, 67, 9966. 119. Vuljanic, T.; Bergquist, K.-E.; Clausen, H.; Roy, S.; Kihlberg, J. Tetrahedron 1996, 52, 7983. 120. Gierasch, T. M.; Shi, Z.; Verdine, G. L. Org. Lett. 2003, 5, 621. 121. Pigza, J. A.; Han, J.-S.; Chandra, A.; Mutnick, D.; Pink, M.; Johnston, J. N. J. Org. Chem. 2012, 78, 822.
摘要: Chapter 1. Mild and Highly α-Selective O-Sialylation Method Based on Pre-activation: Access to Gangliosides Hp-s1, DSG-A, and their Analogues. In Chapter 1, we described the imortance of Gangliosides Hp-s1, DSG-A and by using various methods, these molecules are synthesized. For the stereoselective installation of alpha sialosides to glycosyl acceptors, we developed the mild and effective method. The method has selectivity for promary acceptors over secondary. The ceramide was assembled by using commercially available raw materials which is shortest till date reported. In part II, we designed the molecules with modified ceramide part and synthesized them according to literature reports. Finally after having all compunds in hand, we tested them for neurotological activites which will help for further structure activity relationship study. Chapter 2. Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine glycopeptide. This chapter describes the glycopeptides and its potential applications for chemotherapy and imaging probe for tumor angiogenesis. We successively developed the chemical method to synthesis of di-, tri-, and tetra-saccharide glucosamine and coupled them with lipid chains. The deprotection and purification was tackled according to various techniques.The chain length of sugars can be increase by using the same method. We hope a significant achievement to develop a new drug which can be a selective to tumor cells.
URI: http://hdl.handle.net/11455/96327
文章公開時間: 10000-01-01
顯示於類別:化學系所

文件中的檔案:
檔案 大小格式 
nchu-106-8103051004-1.pdf44.14 MBAdobe PDF 請求副本


在 DSpace 系統中的文件,除了特別指名其著作權條款之外,均受到著作權保護,並且保留所有的權利。