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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 王正中(Cheng-Chung Wang) | |
| dc.contributor.author | Chia-Hui Wu | en |
| dc.contributor.author | 吳佳蕙 | zh_TW |
| dc.date.accessioned | 2021-05-19T17:43:01Z | - |
| dc.date.available | 2023-11-29 | |
| dc.date.available | 2021-05-19T17:43:01Z | - |
| dc.date.copyright | 2018-11-29 | |
| dc.date.issued | 2018 | |
| dc.date.submitted | 2018-11-28 | |
| dc.identifier.citation | [1] Varki, A.; Cummings, R. D.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E. Essentials of Glycobiology; second ed.; Cold Spring Harbor: New York, 2009.
[2] Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370-2376. [3] (a) Aminoff, D.; Bruegge, W. F.; Bell, W. C.; Sarpolis, K.; Williams, R. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 1521-1524; (b) Fearon, D. T. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 1971-1975. [4] (a) Heimburg-Molinaro, J.; Rittenhouse-Olson, K. In Glycomics: Methods and Protocols; Packer, N. H., Karlsson, N. G., Eds.; Humana Press: Totowa, NJ, 2009, 341-357; (b) Rabinovich, G. A.; Toscano, M. A. Nat. Rev. Immunol. 2009, 9, 338-352. [5] (a) Thijssen, V. L.; Heusschen, R.; Caers, J.; Griffioen, A. W. BBA. Rev. Cancer 2015, 1855, 235-247; (b) Perillo, N. L.; Marcus, M. E.; Baum, L. G. J. Mol. Med. 1998, 76, 402-412; (c) Danguy, A.; Camby, I.; Kiss, R. BBA. Gen. Subjects 2002, 1572, 285-293; (d) van den Brûle, F.; Califice, S.; Castronovo, V. Glycoconjugate J. 2002, 19, 537-542; (e) Song, L.; Tang, J.-w.; Owusu, L.; Sun, M.-Z.; Wu, J.; Zhang, J. Clin. Chim. Acta 2014, 431, 185-191; (f) Pinho, S. S.; Reis, C. A. Nat. Rev. Cancer 2015, 15, 540-555. [6] (a) Plachta, N.; Annaheim, C.; Bissiere, S.; Lin, S.; Ruegg, M.; Hoving, S.; Muller, D.; Poirier, F.; Bibel, M.; Barde, Y. A. Nat. Neurosci. 2007, 10, 712-719; (b) Kato, T.; Kurita, K.; Seino, T.; Kadoya, T.; Horie, H.; Wada, M.; Kawanami, T.; Daimon, M.; Hirano, A. Biochem. Biophys. Res. Commun. 2001, 282, 166-172; (c) Zhou, J.-Y.; Afjehi-Sadat, L.; Asress, S.; Duong, D. M.; Cudkowicz, M.; Glass, J. D.; Peng, J. J. Proteome Res. 2010, 9, 5133-5141; (d) Schneider, A.; Simons, M. Cell Tissue Res. 2013, 352, 33-47. [7] (a) Al-Ansari, S.; Zeebregts, C. J.; Slart, R. H. J. A.; Peppelenbosch, M.; Tio, R. A. Trends Cardiovasc. Med. 2009, 19, 164-169; (b) Iacobini, C.; Amadio, L.; Oddi, G.; Ricci, C.; Barsotti, P.; Missori, S.; Sorcini, M.; Mario, U.; Pricci, F.; Pugliese, G. J. Am. Soc. Nephrol. 2003, 14, 264S-270. [8] (a) Hutt Andrew, J. Chirality 1991, 3, 161-164; (b) Hutt, A. J.; Caldwell, J. Clin. Pharmacokinet. 1984, 9, 371-373; (c) Beckett, A. H.; Shenoy, E. V. B. J. Pharm. Pharmacol. 1973, 25, 793-799; (d) Sekhon, B. S. J. Mod. Med. Chem. 2013, 1, 10-36. [9] Kuszmann, J. In The Organic Chemistry of Sugars; Levy, D. E., Fügedi, P., Eds.; Taylor & Francis Group: Florida, 2006, 45-46. [10] (a) Chao, C. S.; Li, C. W.; Chen, M. C.; Chang, S. S.; Mong, K. K. Chem. Eur. J. 2009, 15, 10972-10982; (b) Chao, C. S.; Lin, C. Y.; Mulani, S.; Hung, W. C.; Mong, K. K. Chem. Eur. J. 2011, 17, 12193-12202; (c) Chao, C.-S.; Yen, Y.-F.; Hung, W.-C.; Mong, K.-K. T. Adv. Synth. Catal. 2011, 353, 879-884; (d) Braccini, I.; Derouet, C.; Esnault, J.; de Penhoat, C. H. e.; Mallet, J. M.; Michon, V.; Sinaÿ, P. Carbohydr. Res. 1993, 246, 23-41. [11] (a) Demchenko, A. V.; Stauch, T.; Boons, G.-J. Synlett 1997, 818-820; (b) Lahmann, M.; Oscarson, S. Org. Lett. 2000, 2, 3881-3882; (c) Lönn, H. J. carbohyd. chem. 1987, 6, 301-306; (d) Ishiwata, A.; Munemura, Y.; Ito, Y. Tetrahedron 2008, 64, 92-102. [12] Demchenko, A. V. Synlett 2003, 1225-1240. [13] Satoh, H.; Hansen, H. S.; Manabe, S.; van Gunsteren, W. F.; Hünenberger, P. H. J. Chem. Theory Comput. 2010, 6, 1783-1797. [14] Smoot, J. T.; Pornsuriyasak, P.; Demchenko, A. V. Angew. Chem. Int. Ed. 2005, 44, 7123-7126. [15] (a) Yasomanee, J. P.; Demchenko, A. V. J. Am. Chem. Soc. 2012, 134, 20097-20102; (b) Yasomanee, J. P.; Demchenko, A. V. Angew. Chem. Int. Ed. 2014, 53, 10453-10456; (c) Pistorio, S. G.; Yasomanee, J. P.; Demchenko, A. V. Org. Lett. 2014, 16, 716-719; (d) Kayastha, A. K.; Jia, X. G.; Yasomanee, J. P.; Demchenko, A. V. Org. Lett. 2015, 17, 4448-4451; (e) Yasomanee, J. P.; Parameswar, A. R.; Pornsuriyasak, P.; Rath, N. P.; Demchenko, A. V. Org. Biomol. Chem. 2016, 14, 3159-3169. [16] Fraser-Reid, B.; Wu, Z.; Udodong, U. E.; Ottosson, H. J. Org. Chem. 1990, 55, 6068-6070. [17] (a) Kamat, M. N.; Demchenko, A. V. Org. Lett. 2005, 7, 3215-3218; (b) Smoot, J. T.; Demchenko, A. V. J. Org. Chem. 2008, 73, 8838-8850. [18] Crich, D.; Li, M. Org. Lett. 2007, 9, 4115-4118. [19] (a) Pedersen, C. M.; Nordstrøm, L. U.; Bols, M. J. Am. Chem. Soc. 2007, 129, 9222-9235; (b) Jensen, H. H.; Pedersen, C. M.; Bols, M. Chem. Eur. J. 2007, 13, 7576-7582. [20] Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. [21] (a) Wang, Y.; Huang, X.; Zhang, L.-H.; Ye, X.-S. Org. Lett. 2004, 6, 4415-4417; (b) Wang, Y.; Yan, Q.; Wu, J.; Zhang, L.-H.; Ye, X.-S. Tetrahedron 2005, 61, 4313-4321. [22] Huang, X.; Huang, L.; Wang, H.; Ye, X.-S. Angew. Chem. Int. Ed. 2004, 43, 5221-5224. [23] (a) Pornsuriyasak, P.; Demchenko, A. V. Tetrahedron: Asymmetry 2005, 16, 433-439; (b) Huang, L.; Wang, Z.; Li, X.; Ye, X. S.; Huang, X. Carbohydr. Res. 2006, 341, 1669-1679; (c) Huang, L.; Huang, X. Chem. Eur. J. 2007, 13, 529-540; (d) Miermont, A.; Zeng, Y.; Jing, Y.; Ye, X.-s.; Huang, X. J. Org. Chem. 2007, 72, 8958-8961; (e) Wang, Z.; Zhou, L.; El-Boubbou, K.; Ye, X.-S.; Huang, X. J. Org. Chem. 2007, 72, 6409-6420; (f) Sun, B.; Srinivasan, B.; Huang, X. Chem. Eur. J. 2008, 14, 7072-7081; (g) Lu, X.; Kamat, M. N.; Huang, L.; Huang, X. J. Org. Chem. 2009, 74, 7608-7617; (h) Wang, Z.; Xu, Y.; Yang, B.; Tiruchinapally, G.; Sun, B.; Liu, R.; Dulaney, S.; Liu, J.; Huang, X. Chem. Eur. J. 2010, 16, 8365-8375; (i) Crich, D.; Jayalath, P. J. Org. Chem. 2005, 70, 7252-7259; (j) Geng, Y.; Qin, Q.; Ye, X.-S. J. Org. Chem. 2012, 77, 5255-5270; (k) Yang, B.; Yoshida, K.; Yin, Z.; Dai, H.; Kavunja, H.; El-Dakdouki, M. H.; Sungsuwan, S.; Dulaney, S. B.; Huang, X. Angew. Chem. Int. Ed. 2012, 51, 10185-10189; (l) Gao, J.; Guo, Z. J. Org. Chem. 2013, 78, 12717-12725; (m) Verma, V. P.; Wang, C.-C. Chem. Eur. J. 2013, 19, 846-851; (n) Liao, G.; Burgula, S.; Zhou, Z.; Guo, Z. Eur. J. Org. Chem. 2015, 2015, 2942-2951. [24] (a) Huang, M.; Garrett, G. E.; Birlirakis, N.; Bohe, L.; Pratt, D. A.; Crich, D. Nat. Chem. 2012, 4, 663-667; (b) Yang, L.; Qin, Q.; Ye, X.-S. Asian J. Org. Chem. 2013, 2, 30-49; (c) Crich, D.; Sun, S. J. Org. Chem. 1997, 62, 1198-1199. [25] Lee, Y. J.; Lee, K.; Jung, E. H.; Jeon, H. B.; Kim, K. S. Org. Lett. 2005, 7, 3263-3266. [26] Beaver, M. G.; Woerpel, K. A. J. Org. Chem. 2010, 75, 1107-1118. [27] van der Vorm, S.; Hansen, T.; Overkleeft, H. S.; van der Marel, G. A.; Codee, J. D. C. Chem. Sci. 2017, 8, 1867-1875. [28] van der Vorm, S.; Overkleeft, H. S.; van der Marel, G. A.; Codée, J. D. C. J. Org. Chem. 2017, 82, 4793-4811. [29] (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154; (b) Merrifield, R. B. J. Am. Chem. Soc. 1964, 86, 304-305. [30] (a) Neckers, D. C. J. Chem. Educ. 1975, 52, 695-702; (b) Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1985, 82; (c) Bacsa, B.; Bosze, S.; Kappe, C. O. J. Org. Chem. 2010, 75, 2103-2106; (d) Patgiri, A.; Menzenski, M. Z.; Mahon, A. B.; Arora, P. S. Nat. Protocols 2010, 5, 1857-1865; (e) Stolze, S. C.; Meltzer, M.; Ehrmann, M.; Kaiser, M. Chem. Commun. 2010, 46, 8857-8859. [31] (a) Zlatev, I.; Lavergne, T.; Debart, F.; Vasseur, J.-J.; Manoharan, M.; Morvan, F. Org. Lett. 2010, 12, 2190-2193; (b) Letsinger, R. L.; Mahadevan, V. J. Am. Chem. Soc. 1965, 87, 3526-3527. [32] (a) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1990, 114, 10997-10998; (b) Baptiste, B.; Douat-Casassus, C.; Laxmi-Reddy, K.; Godde, F.; Huc, I. J. Org. Chem. 2010, 75, 7175-7185; (c) Long, K.; Edwards, T. A.; Wilson, A. J. Bioorg. Med. Chem. 2013, 21, 4034-4040. [33] (a) Andrade, R. B.; Plante, O. J.; Melean, L. G.; Seeberger, P. H. Org. Lett. 1999, 1, 1811-1814; (b) Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523-1527; (c) Boltje, T. J.; Kim, J. H.; Park, J.; Boons, G. J. Nat. Chem. 2010, 2, 552-557; (d) Walvoort, M. T.; van den Elst, H.; Plante, O. J.; Krock, L.; Seeberger, P. H.; Overkleeft, H. S.; van der Marel, G. A.; Codee, J. D. Angew. Chem. Int. Ed. 2012, 51, 4393-4396; (e) Walvoort, M. T. C.; Volbeda, A. G.; Reintjens, N. R. M.; Elst, H.; Plante, O. J.; Overkleeft, H. S.; Marel, G.; Codée, J. D. C. Org. Lett. 2012, 14, 3776-3779; (f) Calin, O.; Eller, S.; Seeberger, P. H. Angew. Chem. Int. Ed. 2013, 52, 5862-5865; (g) Eller, S.; Collot, M.; Yin, J.; Hahm, H. S.; Seeberger, P. H. Angew. Chem. Int. Ed. 2013, 52, 5858-5861. [34] (a) Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646-10647; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272; (c) Cohrt, A. E.; Jensen, J. F.; Nielsen, T. E. Org. Lett. 2010, 12, 5414-5417; (d) Khan, S. N.; Kim, A.; Grubbs, R. H.; Kwon, Y.-U. Org. Lett. 2011, 13, 1582-1585; (e) Schaffert, D.; Badgujar, N.; Wagner, E. Org. Lett. 2011, 13, 1586-1589. [35] Merrifield, R. B. Angew. Chem. Int. Ed. Engl. 1985, 24, 799-892. [36] Wang, S.-S. J. Am. Chem. Soc. 1973, 95, 1328-1333. [37] Schuerch, C.; Frechet, J. M. J. Am. Chem. Soc. 1971, 93, 492-496. [38] Hayatsu, H.; Khorana, H. G. J. Am. Chem. Soc. 1967, 89, 3880-3887. [39] James, I. W. Tetrahedron 1999, 55, 4855-4946. [40] (a) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157; (b) Seeberger, P. H.; Haase, W.-C. Chem. Rev. 2000, 100, 4349-4394. [41] (a) Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790; (b) Silva, D. J.; Wang, H.; Allanson, N. M.; Jain, R. K.; Sofia, M. J. J. Org. Chem. 1999, 64, 5926-5929. [42] Schleyer, A.; Meldal, M.; Manat, R.; Paulsen, H.; Bock, K. Angew. Chem. Int. Ed. Engl. 1997, 36, 1976-1978. [43] (a) Deegan, T. L.; Gooding, O. W.; Baudart, S.; Porco Jr, J. A. Tetrahedron Lett. 1997, 38, 4973-4976; (b) Kobayashi, S.; Akiyama, R. Tetrahedron Lett. 1998, 39, 9211-9214. [44] Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650-3653. [45] Srivastava, S. K.; Haq, W.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 1999, 9, 965-966. [46] Michels, R.; Kato, M.; Heitz, W. Makromol. Chem. 1976, 177, 2311-2320. [47] (a) Ruhland, T.; Andersen, K.; Pedersen, H. J. Org. Chem. 1998, 63, 9204-9211; (b) C. Nicolaou, K.; Pastor, J.; Barluenga, S.; Winssinger, N. Chem. Commun. 1998, 1947-1948. [48] (a) Kurth, M. J.; Ahlberg Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Kang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862-5864; (b) F. Tietze, L.; Hippe, T.; Steinmetz, A. Chem. Commun. 1998, 793-794; (c) Kobayashi, S.; Hachiya, I.; Yasuda, M. Tetrahedron Lett. 1996, 37, 5569-5572; (d) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809-2812. [49] Rich, D. H.; Gurwara, S. K. J. Chem. Soc., Chem. Commun. 1973, 610-611. [50] (a) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133; (b) Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575-1579; (c) Ajayaghosh, A.; Pillai, V. N. R. J. Org. Chem. 1990, 55, 2826-2829; (d) Kumar, K. S.; Rajasekharan Pillai, V. N. Tetrahedron 1999, 55, 10437-10446; (e) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem. Int. Ed. 1998, 37, 1559-1561; (f) Zehavi, U.; Patchornik, A. J. Am. Chem. Soc. 1973, 95, 5673-5677. [51] (a) Palomo, J. M. RSC Adv. 2014, 4, 32658-32672; (b) Made, V.; Els-Heindl, S.; Beck-Sickinger, A. G. Beilstein J. Org. Chem. 2014, 10, 1197-1212; (c) Mijalis, A. J.; Thomas Iii, D. A.; Simon, M. D.; Adamo, A.; Beaumont, R.; Jensen, K. F.; Pentelute, B. L. Nat. Chem. Biol. 2017, 13, 464-466; (d) Abdel-Aal, A.-B. M.; Papageorgiou, G.; Quibell, M.; Offer, J. Chem. Commun. 2014, 50, 8316-8319; (e) Masuda, K.; Ooyama, H.; Shikano, K.; Kondo, K.; Furumitsu, M.; Iwakoshi-Ukena, E.; Ukena, K. J. Pept. Sci. 2015, 21, 454-460; (f) Boll, E.; Drobecq, H.; Ollivier, N.; Blanpain, A.; Raibaut, L.; Desmet, R.; Vicogne, J.; Melnyk, O. Nat. Protocols 2015, 10, 269-292; (g) Harmand, T. J.; Murar, C. E.; Bode, J. W. Nat. Protocols 2016, 11, 1130-1147. [52] (a) Krock, L.; Esposito, D.; Castagner, B.; Wang, C.-C.; Bindschadler, P.; Seeberger, P. H. Chem. Sci. 2012, 3, 1617-1622; (b) Hahm, H. S.; Schlegel, M. K.; Hurevich, M.; Eller, S.; Schuhmacher, F.; Hofmann, J.; Pagel, K.; Seeberger, P. H. Proc. Natl. Acad. Sci. U.S.A. 2017, 114, E3385-E3389; (c) Seeberger, P. H. Acc. Chem. Res. 2015, 48, 1450-1463. [53] (a) Bartetzko, M. P.; Schuhmacher, F.; Hahm, H. S.; Seeberger, P. H.; Pfrengle, F. Org. Lett. 2015, 17, 4344-4347; (b) Fair, R. J.; Hahm, H. S.; Seeberger, P. H. Chem. Commun. 2015, 51, 6183-6185. [54] Hurevich, M.; Seeberger, P. H. Chem. Commun. 2014, 50, 1851-1853. [55] (a) Weishaupt, M. W.; Hahm, H. S.; Geissner, A.; Seeberger, P. H. Chem. Commun. 2017, 53, 3591-3594; (b) Bartetzko, M. P.; Schuhmacher, F.; Seeberger, P. H.; Pfrengle, F. J. Org. Chem. 2017, 82, 1842-1850; (c) Routenberg Love, K.; Seeberger, P. H. Angew. Chem. Int. Ed. Engl. 2004, 43, 602-605. [56] Werz, D. B.; Castagner, B.; Seeberger, P. H. J. Am. Chem. Soc. 2007, 129, 2770-2771. [57] (a) Palmacci, E. R.; Plante, O. J.; Hewitt, M. C.; Seeberger, P. H. Helv. Chim. Acta 2003, 86, 3975-3990; (b) Ratner, D. M.; Swanson, E. R.; Seeberger, P. H. Org. Lett. 2003, 5, 4717-4720; (c) Codee, J. D.; Krock, L.; Castagner, B.; Seeberger, P. H. Chem. Eur. J. 2008, 14, 3987-3994. [58] (a) Hurevich, M.; Kandasamy, J.; Ponnappa, B. M.; Collot, M.; Kopetzki, D.; McQuade, D. T.; Seeberger, P. H. Org. Lett. 2014, 16, 1794-1797; (b) Schmidt, D.; Schuhmacher, F.; Geissner, A.; Seeberger, P. H.; Pfrengle, F. Chem. Eur. J. 2015, 21, 5709-5713; (c) Hahm, H. S.; Hurevich, M.; Seeberger, P. H. Nat. Commun. 2016, 7, 12482; (d) Hahm, H. S.; Liang, C. F.; Lai, C. H.; Fair, R. J.; Schuhmacher, F.; Seeberger, P. H. J. Org. Chem. 2016, 81, 5866-5877; (e) Dallabernardina, P.; Schuhmacher, F.; Seeberger, P. H.; Pfrengle, F. Chem. Eur. J. 2017, 23, 3191-3196; (f) Senf, D.; Ruprecht, C.; de Kruijff, G. H. M.; Simonetti, S. O.; Schuhmacher, F.; Seeberger, P. H.; Pfrengle, F. Chem. Eur. J. 2017, 23, 3197-3205. [59] Kulkarni, S. S.; Wang, C. C.; Sabbavarapu, N. M.; Podilapu, A. R.; Liao, P. H.; Hung, S. C. Chem. Rev. 2018, 118, 8025-8104. [60] (a) Grice, P.; Leach, A. G.; Ley, S. V.; Massi, A.; Mynett, D. M. J. Comb. Chem. 2000, 2, 491-495; (b) Mogemark, M.; Elofsson, M.; Kihlberg, J. ChemBioChem 2000, 1266-1269; (c) Mogemark, M.; Elofsson, M.; Kihlberg, J. Org. Lett. 2001, 3, 1463-1466; (d) Mogemark, M.; Elofsson, M.; Kihlberg, J. J. Org. Chem. 2003, 68, 7281-7288; (e) Yao, N. H.; He, W. Y.; Lam, K. S.; Liu, G. J. Comb. Chem. 2004, 6, 214-219; (f) Melean, L. G.; Haase, W.-C.; Seeberger, P. H. Tetrahedron Lett. 2000, 41, 4329-4333. [61] (a) Egner, B. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1995, 60, 2652-2653; (b) Halling, P. J.; Ulijn, R. V.; Flitsch, S. L. Curr. Opin. Biotechnol. 2005, 16, 385-392. [62] (a) Chan, T. Y.; Chen, R.; Sofia, M. J.; Smith, B. C.; Glennon, D. Tetrahedron Lett. 1997, 38, 2821-2824; (b) Yan, B. Acc. Chem. Res. 1998, 31, 621-630. [63] Sugiyama, S.; Diakur, J. M. Org. Lett. 2000, 2, 2713-2715. [64] Zeng, Y.; Wang, Z.; Whitfield, D.; Huang, X. J. Org. Chem. 2008, 73, 7952-7962. [65] (a) Fügedi, P.; Garegg, P. J.; Lönn, H.; Norberg, T. Glycoconjugate J. 1987, 4, 97-108; (b) Ranade, S. C.; Demchenko, A. V. J. Carbohyd. Chem. 2013, 32, 1-43. [66] (a) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503; (b) Schmidt, R. R. Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235. [67] (a) Schwarzenbach, D.; Jeanloz, R. W. Carbohydr. Res. 1981, 90, 193-202; (b) Nashed, M. A.; Anderson, L. J. Am. Chem. Soc. 1982, 104, 7282-7286; (c) Ogawa, T.; Kaburagi, T. Carbohydr. Res. 1982, 110, C12-C15; (d) Doboszewski, B.; Zamojski, A. Carbohydr. Res. 1984, 132, 29-38; (e) Aspinall, G. O.; Gurjar, M. K. Carbohydr. Res. 1985, 143, 266-270; (f) Ogawa, T.; Nukada, T. Carbohydr. Res. 1985, 136, 135-152; (g) Koike, K.; Sugimoto, M.; Sato, S.; Ito, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1987, 163, 189-208; (h) Torgov, V. I.; Panossian, C. A.; Shibaev, V. N. Carbohydr. Res. 1987, 161, 97-112; (i) Kihlberg, J.; Frejd, T.; Jansson, K.; Sundin, A.; Magnusson, G. Carbohydr. Res. 1988, 176, 271-286; (j) Tamura, J.-i.; Horito, S.; Yoshimura, J.; Hashimoto, H. Carbohydr. Res. 1990, 207, 153-165; (k) Takeo, K.; Teramoto, Y.; Shimono, Y.; Nitta, Y. Carbohydr. Res. 1991, 209, 167-179; (l) Sugawara, T.; Irie, K.; Iwasawa, H.; Yoshikawa, T.; Okuno, S.; Watanabe, H. K.; Kato, T.; Shibukawa, M.; Ito, Y. Carbohydr. Res. 1992, 230, 117-149; (m) Spohr, U.; Bach, M. Can. J. Chem. 1993, 71, 1943-1954; (n) Spohr, U.; Bach, M.; Spiro, R. G. Can. J. Chem. 1993, 71, 1928-1942; (o) Zhang, Z.; Magnusson, G. J. Org. Chem. 1995, 60, 7304-7315; (p) Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2383-2393; (q) Garegg, P. J.; Hansson, J.; Helland, A.-C.; Oscarson, S. Tetrahedron Lett. 1999, 40, 3049-3052; (r) Matsuoka, K.; Terabatake, M.; Esumi, Y.; Terunuma, D.; Kuzuhara, H. Tetrahedron Lett. 1999, 40, 7839-7842; (s) Gibson, D.; Homans, S. W.; Field, R. A. Tetrahedron: Asymmetry 2009, 20, 730-732; (t) Rosado, L. M.; Meyerhoefer, T. J.; Bett, S. M.; Ilyas, S.; Bululu, L.; Martin, C. A.; Joseph, T. W.; De Castro, M. Eur. J. Org. Chem. 2016, 2016, 2778-2784; (u) Sun, L.; Wu, X.; Xiong, D. C.; Ye, X. S. Angew. Chem. Int. Ed. 2016, 55, 8041-8044. [68] (a) Leigh, D. A.; Smart, J. P.; Truscello, A. M. Carbohydr. Res. 1995, 276, 417-424; (b) Belot, F.; Jacquinet, J.-C. Carbohydr. Res. 1996, 290, 79-86; (c) Li, Z.; Gildersleeve, J. C. J. Am. Chem. Soc. 2006, 128, 11612-11619. [69] Grewal, G.; Kaila, N.; Franck, R. W. J. Org. Chem. 1992, 57, 2084-2092. [70] Frihed, T. G.; Bols, M.; Pedersen, C. M. Chem. Rev. 2015, 115, 4963-5013. [71] (a) Li, X.; Huang, L.; Hu, X.; Huang, X. Org. Biomol. Chem. 2009, 7, 117-127; (b) Andrews, C. W.; Rodebaugh, R.; Fraser-Reid, B. J. Org. Chem. 1996, 61, 5280-5289. [72] (a) Matwiejuk, M.; Thiem, J. Eur. J. Org. Chem. 2011, 2011, 5860-5878; (b) Caputo, R.; Kunz, H.; Mastroianni, D.; Palumbo, G.; Pedatella, S.; Solla, F. Eur. J. Org. Chem. 1999, 1999, 3147-3150. [73] Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020. [74] Adinolfi, M.; Parrilli, M.; Barone, G.; Laonigro, G.; Mangoni, L. Tetrahedron Lett. 1976, 17, 3661-3662. [75] Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334. [76] (a) Crich, D.; Sun, S. Tetrahedron 1998, 54, 8321; (b) Crich, D.; Cai, W. J. Org. Chem. 1999, 64, 4926-4930; (c) Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702-1706; (d) Dasgupta, F.; Garegg, P. J. Carbohydr. Res. 1988, 177, c13-c17. [77] van der Vorm, S.; van Hengst, J. M. A.; Bakker, M.; Overkleeft, H. S.; van der Marel, G. A.; Codee, J. Angew. Chem. Int. Ed. 2018. [78] (a) Lin, Y. H.; Ghosh, B.; Mong, K. K. Chem. Commun. 2012, 48, 10910-10912; (b) Lu, S.-R.; Lai, Y.-H.; Chen, J.-H.; Liu, C.-Y.; Mong, K.-K. T. Angew. Chem. Int. Ed. 2011, 50, 7315-7320; (c) Mulani, S. K.; Hung, W. C.; Ingle, A. B.; Shiau, K. S.; Mong, K. K. Org. Biomol. Chem. 2014, 12, 1184-1197. [79] Hu, J.-C.; Feng, A.-F. W.; Chang, B.-Y.; Lin, C.-H.; Mong, K.-K. T. Org. Biomol. Chem. 2017, 15, 5345-5356. [80] Knerr, L.; Schmidt, R. Synlett 1999, 1802-1804. [81] (a) Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M. J. Org. Chem. 1997, 62, 5660-5661; (b) Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 491-493; (c) Kanemitsu, T.; Kanie, O.; Wong, C.-H. Angew. Chem. Int. Ed. 1998, 37, 3415-3418. [82] (a) Skipski, V.; Peterson, R.; Barclay, M. Biochem. J. 1964, 90, 374-378; (b) Rouser, G.; Fleischer, S.; Yamamoto, A. Lipids 1970, 5, 494-496; (c) Staneck, J. L.; Roberts, G. D. App. Microbiol. 1974, 28, 226-231; (d) Minnikin, D. E.; Hutchinson, I. G. C., A.B.; Goodfellow, M. J. Chromatogr. 1980, 188, 13. [83] Pathigoolla, A.; Pola, R. P.; Sureshan, K. M. Appl. Catal., A 2013, 453, 151-158. [84] (a) Kajihara, Y.; Suzuki, Y.; Yamamoto, N.; Sasaki, K.; Sakakibara, T.; Juneja, L. R. Chem. Eur. J. 2004, 10, 971-985; (b) Maki, Y.; Okamoto, R.; Izumi, M.; Murase, T.; Kajihara, Y. J. Am. Chem. Soc. 2016, 138, 3461-3468. [85] Boxer, M. B.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 2762-2763. [86] Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191. [87] Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024. [88] Smith, M. B. In Organic Synthesis (Third Edition); Academic Press: Oxford, 2010, 587-622. [89] Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896-899. [90] Joseph, A. A.; Verma, V. P.; Liu, X.-Y.; Wu, C.-H.; Dhurandhare, V. M.; Wang, C.-C. Eur. J. Org. Chem. 2012, 2012, 744-753. [91] (a) Kadam, S. T.; Kim, S. S. Green Chem. 2010, 12, 94-98; (b) Shirini, F.; Zolfigol, M. A.; Abedini, M. Monatsh. Chem. 2009, 140, 61-64; (c) Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Chahardahcheric, S.; Tavakoli, Z. J. Organomet. Chem. 2008, 693, 2041-2046; (d) Shaterian, H. R.; Shahrekipoor, F.; Ghashang, M. J. Mol. Catal. A: Chem. 2007, 272, 142-151; (e) Shirakawa, E.; Hironaka, K.; Otsuka, H.; Hayashi, T. Chem. Commun. 2006, 3927-3929; (f) Karimi, B.; Golshani, B. J. Org. Chem. 2000, 65, 7228-7230. [92] Seko, A.; Koketsu, M.; Nishizono, M.; Enoki, Y.; Ibrahim, H. R.; Juneja, L. R.; Kim, M.; Yamamoto, T. BBA. Gen. Subjects 1997, 1335, 23-32. [93] Witschi, M. A.; Gervay-Hague, J. Org. Lett. 2010, 12, 4312-4315. | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/7406 | - |
| dc.description.abstract | 我們在本論文中討論了醣基氯與醣基三氟甲磺酸酯這兩種中間產物於醣鏈結反應中的角色，並提出了可能的反應機構。此反應機構可適用於對甲苯巰基氯/三氟甲磺酸銀與鹵化丁二醯亞胺/三氟甲磺酸的醣催化條件。此外，我們也發現醣受體的活性也會影響立體選擇性：活性越高越容易得到β位向的產物；反之，則越易獲得α位向產物。
我們也將二甲基甲醯胺作為添加物加入固相醣鏈結反應中，效果與其在液相反應中類似，均可獲得較多的α產物。此外，薄層層析法也應用至固相反應中，有利於化學家在固相反應中即時獲得反應的資訊，以便最佳化條件。 最後，我們從蛋黃萃取出寡醣，並應用本實驗室已開發的方法及討論過的反應機制，將此寡醣官能基化，及位置選擇性地安裝上岩藻醣，成為人體中具有的N-聚醣結構，以利於後續的研究。 | zh_TW |
| dc.description.abstract | We have discussed the roles of the intermediates, glycosyl halide and glycosyl triflate, during the glycosylation and proposed a plausible mechanism for p-TolSCl/AgOTf and NXS/TfOH conditions. Additionally, the reactivity of acceptor influences the stereoselectivity; namely, higher reactive acceptor prefers β-glycosylation and lower reactive acceptor favors α-product.
The DMF-assisted stereoglycosylation was utilized in the solid-phase glycosylation successfully. Also, the real-time detection by thin-layer chromatography (TLC) for the solid-phase reaction was investigated and is believed to benefit this field. Finally, we functionalized and fucosylated a nonasaccharide based on the research in this thesis. The obtained nonasaccharide is going to further study. | en |
| dc.description.provenance | Made available in DSpace on 2021-05-19T17:43:01Z (GMT). No. of bitstreams: 1 ntu-107-D00223205-1.pdf: 85287762 bytes, checksum: 1bd789f9acf95b8ecb1d155b51ade78a (MD5) Previous issue date: 2018 | en |
| dc.description.tableofcontents | 致謝 I
Abstract (中文) II Abstract (English) III Abbreviation IV Table of Contents VII List of Figures IX List of Schemes XI List of Tables XIII Chapter 1 Introduction 1 1.1 Biochemical Importance of Carbohydrates 1 1.2 The Influencing Factors on Stereoglycosylaton 3 1.2.1 Anomeric Effect 3 1.2.2 Solvent Effect 4 1.2.3 Neighboring Group Effect 5 1.2.4 Armed/Disarmed Glycosylation 6 1.2.5 Preactivation Glycosylation 9 1.2.6 Acceptor Nucleophilicity 11 1.3 Solid-Phase Synthesis 15 1.3.1 History of Solid-Phase Synthesis 15 1.3.2 Cleavage of Linkers 16 1.3.3 Currents and Predicaments 18 1.4 Motivations 22 Chapter 2 The New Effects in Glycosylation 23 2.1 Preactivation Glycosylation 23 2.1.1 p-TolSCl/AgOTf Preactivation 23 2.1.2 Other Cl-Promoters in Preactivation Glycosylation 26 2.2 N-Halosuccinimide (NXS)/TfOH Glycosylation 38 2.3 Summary 45 Chapter 3 Acceptor Nucleophilicity 47 3.1 Preactivation Glycosylation 47 3.2 Non-Preactivation Glycosylation 51 3.3 Summary 53 Chapter 4 Solid-Phase Synthesis 54 4.1 Ester-Linker Based Solid-Phase Glycosylation 54 4.1.1 Preactivation/Non-Preactivation Strategies 54 4.1.2 Dimethylformamide-Assisted Strategies 56 4.2 Photolabile-Linker Based Solid-Phase Glycosylation 56 4.2.1 Model Studies 56 4.2.2 Real-Time Detection by Thin-Layer Chromatography 60 4.2.3 Applications 63 Chapter 5 Future Work: Functionalization of Nonasaccharide from Egg Yolk 67 5.1 Model Studies-Trimethylsilylation of Alcohols 67 5.2 Regioselective Protection of Nonasaccharide 72 Chapter 6 Conclusions 74 Chapter 7 References 75 Chapter 8 Experimental Section and NMR spectra 88 List of Figures Figure 1. Carbohydrates involve in several biological functions 2 Figure 2. The common N-glycan in human and the O-glycan core structure in mammalian. 2 Figure 3. The dipole-dipole interaction and stereoelectronic hypothesis for anomeric effect 4 Figure 4. The solvent coordination hypothesis. 5 Figure 5. The conformer and counterion distribution hypothesis 5 Figure 6. The C2 participation of ester group 6 Figure 7. (a) Picolinyl group at C2 for 1,2-trans product. (b) Picolinyl or picoloyl group at C3, C4, or C6 for hydrogen-bond mediated aglycone delivery 6 Figure 8. The armed/disarmed donors resulted from the C2 substituents 7 Figure 9. Some representative examples of the classified armed/disarmed glycosides 8 Figure 10. The linkers on resin for different synthetic purposes 16 Figure 11. Nitrobenzyl based photolabile linkers on polystyrene 19 Figure 12. (a) The representative biomolecules. (b) Solid-phase peptide synthesis 19 Figure 13. Glycosyl chlorides was observed in situ from different glycosyl donors 23 Figure 14. The crude NMR of the preactivation under -78 °C with various time in situ. 25 Figure 15. The in situ NMR from the preactivation of p-O2NPhSCl condition 27 Figure 16. The symmetric/unsymmetrical disulfides, the selenyl compounds, and the side-products from self-coupling and hydrolysis. 29 Figure 17. The 1H spectra of α-galactosyl chloride α-69 (a) without any additive; with (b) TolSSTol 73 (0.5 equiv.); (c) TolSSTol 73 (0.5 equiv.) and TTBP (2.0 equiv.); (d) TolSSTol 73 (0.5 equiv.), TTBP (2.0 equiv.), and AgOTf (1.0 equiv.); (e) TolSSTol 73 (0.5 equiv.) and AgOTf (1.0 equiv.) 34 Figure 18. The 13C spectra of α-galactosyl chloride α-69 (a) without any additive; with (b) TolSSTol 73 (0.5 equiv.); (c) TolSSTol 73 (0.5 equiv.), TTBP (2.0 equiv.), and AgOTf (1.0 equiv.); (d) TolSSTol 73 (0.5 equiv.) and AgOTf (1.0 equiv.) 34 Figure 19. The 1H spectra of α-galactosyl chloride α-69 (a) without any additive; (b) with PhSeSePh 75 (0.5 equiv.); (c) with PhSeSePh 75 (0.5 equiv.) and TTBP (2.0 equiv.); (d) with PhSeSePh 75 (0.5 equiv.), TTBP (2.0 equiv.), and AgOTf (1.0 equiv.); (e) with PhSeSePh 75 (0.5 equiv.) and AgOTf (1.0 equiv.) 35 Figure 20. The 13C spectra of α-galactosyl chloride α-69 (a) without any additive; (b) with PhSeSePh 75 (0.5 equiv.); (c) with PhSeSePh 75 (0.5 equiv.) and TTBP (2.0 equiv.); (d) with PhSeSePh 75 (0.5 equiv.), TTBP (2 equiv.) and AgOTf (1.0 equiv.) 36 Figure 21. T1 relaxation time of α-galactosyl chloride α-69 in the presence of (a) TolSSTol 73 and (b) PhSeSePh 75 and of α-galactosyl chloride 82 in the presence of (c) TolSSTol 36 Figure 22. Galactosyl bromide 84 in the crude NBS/TfOH reaction mixture at 300 K 41 Figure 23. Galactosyl iodide 85 in the crude NBS/TfOH reaction mixture at 233 K 42 Figure 24. The trend of α/β-selectivity along with various acceptors 53 Figure 25. The starting materials for DMF-modulated glycosylation 54 Figure 26. TLC analysis for solid-phase reactions by capillary. 60 Figure 27. The conversion yield at the different irradiating time 60 Figure 28. The retrosynthesis of target N-glycan 68 Figure 29. Trimethylsilylation of sugars by HMDS/TMSOTf-catalysis 69 List of Schemes Scheme 1. The RRV determination by a competitive reaction and rate equation 9 Scheme 2. The chemoselective glycosylation by utilizing RRV 10 Scheme 3. Mechanism for the α- and β-glycosylation of 4,6-benzylidene glycosides. 12 Scheme 4. The final products released from Rink amide resin by mild acids. 16 Scheme 5. The glycopeptides released from POEPOP by NaOMe 17 Scheme 6. (a) Oxidative cleavage by DDQ. (b) Sulfur and (c) selenium linkers for final oxidation 17 Scheme 7. Reductive cleavage by (a) Raney reagent, (b) Bu3SnH/AIBN condition, and (c) hydride reagent 18 Scheme 8. Seeberger’s automated solid-phase oligosaccharide synthesis with (a) the chosen linkers and (b) the building blocks; (c) the repeated glycosylation and deprotection to achieve the biologically relevant oligosaccharides 21 Scheme 9. The Proposed pathway for the p-TolSCl/AgOTf preactivation condition 23 Scheme 10. The plausible mechanism of preactivation 26 Scheme 11. The symmetric and unsymmetrical disulfides formation 29 Scheme 12. TTBP participation in preactivation glycosylation 32 Scheme 13. TolSSTol 73 participation in glycosylation 33 Scheme 14. The plausible mechanism for NIS/TfOH system 38 Scheme 15. Model studies for the galactosyl side products 43 Scheme 16. The formation of N-(tolylthio)phthalamide 87 44 Scheme 17. The plausible mechanism for NXS/TfOH glycosylation. 45 Scheme 18. The nitrobenzyl alcohol was exposed under 254-nm UV lamp. 58 Scheme 19. The photolabile linker on Merrifield resin was irradiated by 254-nm UV lamp. 59 Scheme 20. 4,6-O-Benzylidene galactosylation in (a) solid phase and (b) solution phase. 61 Scheme 21. The solid-phase click reaction 64 Scheme 22. The solid-phase synthesis of aminopentyl glucoside 65 Scheme 23. One-pot protection through fully trimethylsilylated glucopyranosides 69 Scheme 24. Natural oligosaccharide 137 extracted from egg yolk was functionalized to achieve the nonasaccharide 160 or 161 73 List of Tables Table 1. Preactivation glycosylation of thioglycosyl donors 11 Table 2. The glycosylations of mannosyl sulfoxide under preactivation manner 13 Table 3. The glycosylation of arabinofuranoside under non-preactivation manner 14 Table 4. Thiogalactoside 11 was treated by Huang and Ye’s condition 24 Table 5. Glycosylations with different chloro-promoters 28 Table 6. Stereoselectivity effected by chloride promoters 30 Table 7. Non-preactivation glycosylation with different chloride promoters 31 Table 8. Non-preactivation glycosylation with N-halosuccinimide 39 Table 9. NXS/TfOH conditions for preactivation 40 Table 10. p-TolSCl/AgOTf promoted glycosylation with several acceptors under preactivation 48 Table 11. PhSeCl/AgOTf promoted glycosylation with several acceptors under preactivation 49 Table 12. The glycosylation of the glucoside donor 21 and several acceptors 50 Table 13. p-TolSCl/AgOTf promoted glycosylations under non-preactivation. 51 Table 14. PhSeCl and p-O2NPhSCl/AgOTf promoted glycosylations under non-preactivation 52 Table 15. Solid-phase glycosylation under preactivation/non-preactivation procedure 55 Table 16. DMF-modulated Solid-phase glycosylation 57 Table 17. Examining TLC analysis for the solid-phase reactions with different substrates. 62 Table 18. Trimethylsilylation for aryl alcohols 71 | |
| dc.language.iso | en | |
| dc.subject | 立體位向控制 | zh_TW |
| dc.subject | 固相反應 | zh_TW |
| dc.subject | 預活化醣鏈結反應 | zh_TW |
| dc.subject | 薄膜層析法 | zh_TW |
| dc.subject | 醣基氯化物 | zh_TW |
| dc.subject | thin-layer chromatography | en |
| dc.subject | glycosyl chloride | en |
| dc.subject | preactivation glycosylation | en |
| dc.subject | stereoselectivity controlling | en |
| dc.subject | solid-phase reaction | en |
| dc.title | 促進劑與醣受體於醣鏈結反應中的影響與薄膜層析法於固相反應之即時分析 | zh_TW |
| dc.title | The influence of halide promoters and acceptors on glycosylation and the real-time analysis by thin-layer chromatography for solid-phase reaction. | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 107-1 | |
| dc.description.degree | 博士 | |
| dc.contributor.coadvisor | 吳世雄(Shih-Hsiung Wu) | |
| dc.contributor.oralexamcommittee | 鍾博文(Po-Wen CHung),李文山(Wen-Shan Li),李賢明(Hsien-Ming Li) | |
| dc.subject.keyword | 醣基氯化物,預活化醣鏈結反應,立體位向控制,固相反應,薄膜層析法, | zh_TW |
| dc.subject.keyword | glycosyl chloride,preactivation glycosylation,stereoselectivity controlling,solid-phase reaction,thin-layer chromatography, | en |
| dc.relation.page | 195 | |
| dc.identifier.doi | 10.6342/NTU201804303 | |
| dc.rights.note | 同意授權(全球公開) | |
| dc.date.accepted | 2018-11-28 | |
| dc.contributor.author-college | 理學院 | zh_TW |
| dc.contributor.author-dept | 化學研究所 | zh_TW |
| dc.date.embargo-lift | 2023-11-29 | - |
| 顯示於系所單位： | 化學系 | |
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