奈米粒子系統應用: 酵素固化與高通量酵素篩選平台開發

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研究生：	游景晴 YU, CHING-CHING
論文名稱：	奈米粒子系統應用: 酵素固化與高通量酵素篩選平台開發 Development of Nanoparticle-based System for Enzyme Immobilization and High Through-put Enzyme Screening
指導教授：	林俊成
口試委員:	李耀坤林俊宏林伯樵陳貴通
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2012
畢業學年度：	100
語文別：	英文
論文頁數：	151
中文關鍵詞：	酵素固化、磁性奈米粒子、天然化學連結法、唾液酸轉移酶、金奈米粒子、比色法、聚唾液酸轉移酶、聚唾液酸、綠色化學
外文關鍵詞：	enzyme immobilization, magnetic nanoparticle, native chamical ligation, sialyltransferase, gold nanoparticle, colorimetric assay, polysialyltransferase, polysialic acid, green chemistry
相關次數：	點閱：2 下載：0
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近年來，將奈米粒子這類新穎的材料應用在生物體系統受到相當多的重視。結合奈米粒子與生物分子成為一個混合式的微小材料，其應用性可小到奈米等級的單一電子機制探討，也可大到生醫材料診斷方法的開發。
由於磁性奈米粒子本身所具有的高表面積-體積比以及其超順磁性，使得這類奈米材料成為一相當適合用在酵素固化的平台。本論文將利用此材料，並探討位向專一方式之酵素固定化。結合Intein蛋白質表達系統與磁性奈米粒子，透過Native Chemical Ligation (NCL)將CMP-sialic acid synthetase (CSS)與alpha-2,3sialyl -transferase (PmST1)固化於磁性奈米粒子上。不需經過繁瑣之純化步驟，就能將酵素C端位以位向專一性且共價鍵結方式固化於磁性奈米粒子，並且利用磁鐵就能夠快速地將酵素於反應溶液中分離。相較於傳統以隨機醯胺鍵形成進行酵素固定化，本方法以位向專一性方式固化，其酵素反應性較傳統固化方式高出許多。我們並探討酵素在磁性奈米粒子上的含量、酵素與磁性奈米粒子之間的連接長度與其反應活性的關係。我們成功結合兩種酵素功能化磁性奈米粒子進行一鍋化反應合成三醣體GM3衍生物。此外，固化後之酵素功能化磁性奈米粒子能夠長時間保存；於多次重複使用後，依然維持相當好之反應性。結合生物與奈米技術之酵素功能化磁性奈米粒子，不單單能夠應用於有機合成，酵素的回收再利用，更加提高了其經濟價值。
金奈米粒子由於其容易調控粒子大小、可修飾粒子表面、大的表面積/體積比與特殊的光學性質。因此金奈米粒子已被應用於與各種蛋白質、抗體、凝集素及小分子耦合，並有許多的應用。金奈米粒子由於其粒徑在數十奈米至數百奈米間，正好與蛋白質/酵素作用的細胞大小相近，因此金奈米粒子對醣類與蛋白質/酵素作用的研究，可說是一相當優良的載體。本論文將利用四醣體GD3包覆的13 nm金奈米粒子，透過alpha-2,8-polysialyltransferase (PST) 反應，在金奈米粒子表面合成聚唾液酸多醣體。並利用雙點突變之唾液酸水解酶，藉由其與聚唾液酸之間強大的作用力，以偵測聚唾液酸的生成。此方法採用比色法偵測聚唾液酸，並能夠在細胞粗萃液的環境之下進行聚唾液酸的偵測；不僅能在96孔盤中操作，並且免除了傳統ELISA偵測方法中繁複的清洗過程。

謝誌    ....................................................................................................................V
中文摘要    ...................................................................................................................VI
Abstract    ................................................................................................................VIII
Abbreviations    XI
Chapter 1. Immobilization of Enzyme and Enzyme Activity by Gold Nanoparticle-based Colorimetric Assay    - 1 -
1 Immobilization of enzyme    - 1 -
1.1 Classical non-specific covalent protein immobilization    - 1 -
1.2 Enzyme catalyzed site-specific covalent protein immobilization    - 3 -
1.3 Bioorthogonal chemistry for site-specific protein immobilization    - 12 -
1.4 Immobilization methods derived from native chemical ligation    - 16 -
1.5 Immobilization of carbohydrate-active enzymes    - 22 -
1.6 Persepctives    - 26 -
2 Enzyme Activity by Gold Nanoparticle-based Colorimetric Assay    - 27 -
2.1 Gold Nanoparticles-based Colorimetric biosensing Assay    - 27 -
2.2 Localized Surface Plasmon Resonance of AuNPs    - 28 -
2.3 Perspective and specific aim    - 34 -
Chapter 2. Site-specific Immobilization of Enzymes on Magnetic Nanoparticles and Their Use in Organic Synthesis    - 37 -
1 Results and Discussion    - 37 -
1.1 Synthesis and characterization of Cys@MNPs.    - 37 -
1.2 Cloning, overexpression and purification of truncated α2,3-sialyltransferase from Pasteurella multocida    - 41 -
1.4 Evaluation of PmST1@MNP activity    - 48 -
1.5 Kinetics of immobilized PmST1    - 49 -
1.6 Reusability and productivity of enzyme@MNPs    - 52 -
2 Conclusions    - 54 -
3. Experimental Sections    - 55 -
3.1 Materials and methods    - 55 -
3.2. Cloning, overexpression, and purification of the full-length sialyl -transferase from Pasteurella multocida (Pm0188Ph)    - 56 -
2.3 Preparation of amino-functionalized magnetic nanoparticles (NH2@MNP)...    - 58 -
2.4 Synthesis of cysteine-functionalized magnetic nanoparticles (MNP1)    - 58 -
2.5 Synthesis of cysteine-functionalized magnetic nanoparticles (MNP2)    - 59 -
2.6 Synthesis of Cys-functionalized magnetic nanoparticles (MNP3)    - 59 -
2.7 Site-specific immobilization of PmST1 on Cys@MNPs    - 59 -
2.8 Quantification of the purified and MNP-immobilized proteins    - 60 -
2.9 Sialyltransferase activity assay    - 60 -
2.10 Kinetic studies of PmST1 sialyltransferase    - 61 -
2.11 Recycling of enzyme@MNPs    - 61 -
2.12 Synthetic procedures    - 62 -
Chapter 3. Gold Nanoparticles-based Colorimetric Enzyme Assay for High Through-put Screening    - 68 -
1 Results and Discussion    - 68 -
1.1 Design of AuNP-based Colorimetric α2,8-polysialic acids detection    - 68 -
1.2 Enzymatic synthesis of thiolated oligosaccharide ligand GM3 and GD3    - 68 -
1.3 Fabrication of GD3-conjugated AuNPs    - 70 -
1.4 Examination of polysialic acid formation on AuNPs    - 72 -
1.5 Investigation the effect of GD3 density for PSA elongation on AuNP    - 75 -
1.6 Optimization of AuNPs and EndoNF DM concentrations for HTS assay    .......- 76 -
2 Conclusions    - 77 -
3 Experimental Sections    - 78 -
3.1 Materials and methods    - 78 -
3.2 Overexpression and purification of the truncated α2,8-polysialyltransferase from Neisseria meningitidis (PST)    - 79 -
3.3 Overexpression and purification of the bifunctional α2,3/2,8-polysialyl -transferase from Campylobacter jejuni (Cst-IIΔ32)    - 80 -
3.4 Overexpression and purification of the α2,3-polysialyltransferase from Campylobacter jejuni (Cst I)    - 80 -
3.5 Overexpression and purification of the endo-sialidase double mutant from bacteriophage K1F (EndoNF DM) and GFP-fused endo-sialidase double mutant (GFP-EndoNF DM)    - 81 -
3.6 Synthesis of citrate-stabilized gold nanoparticles    - 83 -
3.7 Fabrication of oligosaccharide conjugated gold nanoparticles    - 83 -
3.8 Enzymatic polysialylation catalyzed by α2,8-polysialyltransferase and detection on oligosaccharide-assembled gold nanoparticles    - 84 -
3.9 Synthetic procedures    - 84 -
Chapter 4. The High Through-put Screening Method for α2,8-polysialyl -transferase (Graduate Students Study Abroad Program)    - 89 -
1 Introduction    - 89 -
2 Specific aim    - 91 -
3 Results and Discussion    - 92 -
3.1 Design of plate-based α2,8-polysialyltransferase assay    - 92 -
3.2 Synthesis of azido-oligosaccharides    - 93 -
3.3 Examination of GT3 plate-based fluorescence assay    - 95 -
3.4 Optimizing of substrate density for PST assay    - 97 -
3.5 Detection of cell lysate activity    - 98 -
4 Conclusions    - 99 -
5 Experimental Sections    - 100 -
5.1 Materials and methods    - 100 -
5.2 Fabrication of alkynated micro-titer plates    - 100 -
5.3 Immobilization of azido-oligosaccharides on microplates by click chemistry    - 101 -
5.4 α2,8-polysialyltransferase reaction in oligosaccharide-microplates    - 101 -
5.5 Synthetic procedure    - 102 -
Chapter 5. Perspectives    - 109 -
References:.    - 111 -
Publications:    - 121 -

                                

1. Drauz, K.; and Waldmann, H. Vol. I-III, Wiley-VCH, Weinheim, 2002.
2. Koeller, K. M.; Wong, C.-H. Nature 2001, 409, 232.
3. Schmid, A.; Dordick, J. S.; Hauer, B.; Kiener, A.; Wubbolt, M.; Witholt, B. Nature 2001, 409, 258.
4. Toscano, M. D.; Woycechowsky, K. J.; Hilvert, D. Angew. Chem. Int. Ed. 2007, 46, 3212.
5. Sheldon, R. A. Adv. Synth. Catal. 2007, 349, 1289.
6. Hanefeld, U.; Gardossi, L.; and Magner, E. Chem. Soc. Rev. 2009, 38, 453.
7. Mateo, C.; Palomo, J. M.; Fernandez-Lorente, G.; Guisan, J. M.; Fernandez- Lafuente, R. Enzyme Microb. Technol. 2007, 40, 1451.
8. Cao, L. Curr. Opin. Chem. Biol. 2005, 9, 217.
9. Dyal, A.; Loos, K.; Noto, M.; Chang, S. W.; Spagnoli, C.; Shafi, K. V. P. M.; Ulman, A.; Cowman, M.; and Gross, R. A. J. Am. Chem. Soc. 2003, 125, 1684.
10. Wang, W.; Xu, Y.; Wang, D. I. C.; Li, Z. J. Am. Chem. Soc. 2009, 131, 12892.
11. (a) MacBeath, G.; Schreiber, S. L. Science 2000, 289, 1760. (b) Angenendt, P.; Glökler, J.; Murphy, D.; Lehrach, H.; Cahill, D. J. Anal. Biochem. 2002, 309, 253.
12. Zhu, H.; Bilgin, M.; Bangham, R.; Hall, D.; Casamayor, A.; Bertone, P.; Lan, N.; Jansen, R.; Bidlingmaier, S.; Houfek, T.; Mitchell, T.; Miller, P.; Dean, R. A.; Gerstein, M.; Snyder, M. Science 2001, 293, 2101.
13. Rusmini, F.; Zhong, Z.; Feijen, J. Biomacromolecules 2007, 8, 1775.
14. Hermanson, G. T. Bioconjugate Techniques, Academic Press, San Diego, 2008.
15. Niemeyer, C. M. Bioconjugation Protocols, Vol. 283, Humana Press, Totowa, NJ, 2008.
16. Jonkheijm, P.; Weinrich, D.; Schröder, H.; Niemeyer, C. M.; Waldmann, H. Angew. Chem. Int. Ed. 2008, 47, 9618.
17. Wong, L. S.; Khan, F.; Micklefield, J. Chem. Rev. 2009, 109, 4025.
18. Lambalot, R. H.; Gehring, A. M.; Flugel, R. S.; Zuber, P.; LaCelle, M.; Marahiel, M. A.; Reid, R.; Khosla, C.; Walsh, C. T. Chem. Biol. 1996, 3, 923.
19. Yin, J.; Liu, F.; Li, X.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 7754.
20. Yin, J.; Straight, P. D.; McLoughlin, S. M.; Zhou, Z.; Lin, A. J.; Golan, D. E.; Kelleher, N. L.; Kolter, R.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15815.
21. Yin, J.; Lin, A. J.; Golan, D. E.; Walsh, C. T. Nat. Protocols 2006, 1, 280.
22. Zhou, Z.; Cironi, P.; Lin, A.; Xu, Y.; Hrvatin, S.; Golan, D.; Silver, P.; Walsh, C.; Yin, J. ACS Chem. Biol. 2007, 2, 337.
23. Wong, L. S.; Thirlway, J. L.; Micklefield, J. J. Am. Chem. Soc. 2008, 130, 12456
24. Sunbul, M.; Yen, M.; Zou, Y.; Yin, J. Chem. Commun. 2008, 5927.
25. Waichman, S.; Bhagawati, M.; Podoplelova, Y.; Reichel, A.; Brunk, A.; Paterok, D.; Piehler, J. Anal. Chem. 2010, 82, 1478.
26. Kho, Y.; Kim, S. C.; Jiang, C.; Barma, D.; Kwon, S. W.; Cheng, J.; Jaunbergs, J.; Weinbaum, C.; Tamanoi, F.; Falck, J.; Zhao, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12479.
27. Gauchet, C.; Labadie, G. R.; and Poulter, C. D. J. Am. Chem. Soc. 2006, 128, 9274.
28. Duckworth, B. P.; Xu, J.; Taton, T. A.; Guo, A.; Distefano, M. D. Bioconjugate Chem. 2006, 17, 967.
29. Weinrich, D.; Lin, P.-C.; Jonkheijm, P.; Nguyen, U. T. T.; Schröder, H.; Niemeyer, C. M.; Alexandrov, K.; Goody, R.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 1252.
30. Rashidian, M.; Song, J. M.; Pricer, R. E.; Distefano, M. D. J. Am. Chem. Soc. 2012, 134, 8455.
31. Kruger, R. G.; Otvos, B.; Frankel, B. A.; Bentley, M.; Dostal, P.; McCafferty, D. G. Biochemistry 2004, 43, 1541.
32. Ton-That, H.; Faull, K. F.; Schneewind, O. J. Biol. Chem. 1997, 272, 22285.
33. Pritz, S.; Wolf, Y.; Kraetke, O.; Klose, J.; Bienert, M.; Beyermann, M. J. Org. Chem. 2007, 72, 3909.
34. Popp, M. W.; Antos, J. M.; Grotenbreg, G. M.; Spooner, E.; Ploegh, H. L. Nat. Chem. Biol. 2007, 3, 707.
35. Antos, J. M.; Miller, G. M.; Grotenbreg, G. M.; Ploegh, H. L. J. Am. Chem. Soc. 2008, 130, 16338.
36. Parthasarathy, R.; Subramanian, S.; Boder, E. T. Bioconjugate Chem. 2007, 18, 469.
37. Chan, L.; Cross, H. F.; She, J. K.; Cavalli, G.; Martins, H. F.; Neylon, C. PloS One 2007, 2, e1164.
38. Clow, F.; Fraser, J. D.; Proft, T. Biotechnol. Lett. 2008, 30, 1603.
39. Ito, T.; Sadamoto, R.; Naruchi, K.; Togame, H.; Takemoto, H.; Kondo, H.; Nishimura, S.-I. Biochemistry 2010, 49, 2604.
40. Sinisi, A.; Popp, M. W.-L.; Antos, J. M.; Pansegrau, W.; Savino, S.; Nissum, M.; Rappuoli, R.; Ploegh, H. L.; Buti, L.; Bioconjugate Chem. 2012, 23, 1119.
41. Jiang, R.; Weingart, J.; Zhang, H.; Ma, Y.; Sun, X.-L. Bioconjugate Chem. 2012, 23, 643.
42. Tanaka, Y.; Tsuruda, Y.; Nishi, M.; Kamiya, N.; Goto, M. Org. Biomol. Chem. 2007, 5, 1764.
43. (a) Lin, C.-W.; Ting, A. Y. J. Am. Chem. Soc. 2006, 128, 4542.; (b) Tominaga, J.; Kemori, Y.; Tanaka, Y.; Maruyama, T.; Kamiya, N.; Goto, M.; Chem. Commun. 2007, 401.
44. Tanaka, T.; Kamiya, N.; Nagamune, T. Bioconjugate Chem. 2004, 15, 491.
45. Sletten, E. M.; Bertozzi, C. R. Angew. Chem. Int. Ed. 2009, 48, 6974.
46. Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007.
47. Köhn, M.; Breinbauer, R. Angew. Chem. Int. Ed. 2004, 43, 3106.
48. Soellner, M. B.; Dickson, K. A.; Nilsson, B. L.; and Raines, R. T. J. Am. Chem. Soc. 2003, 125, 11790.
49. Watzke, A.; Köhn, M.; Gutierrez-Rodriguez, M.; Wacker, R.; Schröder, H.; Breinbauer, R.; Kuhlmann, J.; Alexandrov, K.; Niemeyer, C. M.; Goody, R. S.; and Waldmann, H. Angew. Chem. Int. Ed. 2006, 45, 1408.
50. Kalia, J.; Abbott, N. L.; Raines, R. T. Bioconjugate Chem. 2007, 18, 1064.
51. Huisgen, R. Angew. Chem. Int. Ed. 1968, 7, 321.
52. Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem. Int. Ed. 2007, 46, 2101.
53. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
54. Lia, N.; Binder, W. H. J. Mater. Chem. 2011, 21, 16717.
55. Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272.
56. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249.
57. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
58. Lin, P.-C.; Ueng, S.-H.; Tseng, M.-C.; Ko, J.-L.; Huang, K.-T.; Yu, S.-C.; Adak, A. K.; Chen, Y.-J.; Lin, C.-C. Angew. Chem. Int. Ed. 2006, 45, 4286.
59. Lin, P.-C.; Ueng, S.-H.; Yu, S.-C.; Jan, M.-D.; Adak, A. K.; Yu, C.- C.; Lin, C.-C. Org. Lett. 2007, 9, 2131.
60. Dillmore, W. S.; Yousaf, M. N.; Mrksich, M. Langmuir 2004, 20, 7223.
61. Dantas de Araffljo, A.; Palomo, J. M.; Cramer, J.; Köhn, M.; Schröder, H.; Wacker, R.; Niemeyer, C. M.; Alexandrov, K.; Waldmann, H. Angew. Chem. Int. Ed. 2006, 45, 296.
62. Blackman, M. L.; Royzen, M.; Fox, J. M. J. Am. Chem. Soc. 2008, 130, 13518.
63. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923.
64. Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325.
65. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Science 1994, 226, 776.
66. Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. USA 1999, 96, 10068.
67. Kent, S. B. H. Chem. Soc. Rev. 2009, 38, 338.
68. (a) Muir, T. W.; Sondhi, D.; Cole, P. A. Proc. Natl. Acad. Sci. USA 1998, 95, 6705. (b) Muir, T. W. Annu. Rev. Biochem. 2003, 72, 249.
69. Camarero, J. A.; Kwon, Y.; Coleman, M. A. J. Am. Chem. Soc. 2004, 126, 14730.
70. (a) Lesaicherre, M. L.; Uttamchandani, M.; Chen, G. Y.; Yao, S. Q. Bioorg. Med. Chem. Lett. 2002, 12, 2079.; (b) Girish, A.; Sun, H.; Yeo, D. S.; Chen, G. Y.; Chua, T. K.; Yao, S. Q. Bioorg. Med. Chem. Lett. 2005, 15, 2447.
71. Helms, B.; van Baal, I.; Merkx, M.; Meijer, E. W. ChemBioChem 2007, 8, 1790.
72. Yu, C.-C.; Lin, P.-C.; Lin, C.-C. Chem. Commun. 2008, 1308.
73. Yu, C.-C.; Kuo, Y-Y.; Liang, C.-F.; Chien, W.-T.; Wu, H.-T.; Chang, T.-C.; Jan, F.-D.; Lin, C.-C. Bioconjugate Chem. 2012, 23, 714.
74. Kalia, J.; Raines, R. T.; ChemBioChem 2006, 7, 1375.
75. Xia, Z. Y.; Xing, Y.; So, M. K.; Koh, A. L.; Sinclair, R.; Rao, J. H. Anal. Chem. 2008, 80, 8649.
76. Yang, P.; Marinakos, S. M.; Chilkoti, A. Langmuir 2011, 27, 1463
77. (a) Schmaltz, R. M.; Hanson, S. R.; Wong, C.-H. Chem. Rev. 2011, 111, 4259.; (b) Kadokawa, J.-i. Chem. Rev. 2011, 111, 4308.
78. Nishiguchi, S.; Yamada, K.; Fuji, Y.; Shibatani, S.; Toda, A.; Nishimura, S. Chem. Commun. 2001,1944.
79. (a) Augé, C.; Malleron, A.; Tahrat, H.; Marc, A.; Goergen, J. L.; Cerutti, M.; Steelant, W. F. A.; Delannoy, P.; Lubineau, A., Chem. Commun. 2000, 2017.; (b) Ivannikova, T.; Bintein, F.; Malleron, A.; Juliant, S.; Cerutti, M.; Harduin-Lepers, A.; Delannoy, P.; Augé, C.; Lubineau, A. Carbohydr. Res. 2003, 338, 1153.
80. Chen, X.; Fang, J.; Zhang, J.; Liu, Z.; Shao, J.; Kowal, P.; Andreana, P.; Wang, P. G. J. Am. Chem. Soc. 2001, 123, 2081.; (b) Liu, Z.; Zhang, J.; Chen, X.; Wang, P. G., Chembiochem 2002, 3, 348.
81. Naruchi, K.; Nishimura, S. Angew. Chem. Int. Ed. 2011, 50, 1328.
82. Chen, M. L.; Adak, A. K.; Yeh, N. C.; Yang, W. B.; Chuang, Y. J.; Wong, C. H.; Hwang, K. C.; Hwu, J.-R. R.; Hsieh, S. L.; Lin, C. C. Angew. Chem. Int. Ed. 2008, 47, 8627.
83. Lin, P.-C.; Chen, S.-H.; Wang, K.-Y.; Chen, M.-L.; Adak, A. K.; Hwu, J.-R. R.; Chen, Y.-J.; Lin, C.-C. Anal. Chem. 2009, 81, 8774.
84. Timmons, S. C.; Mosher, R. H.; Knowles, S. A.; Jakeman, D. L. Org. Lett. 2007, 9, 857.
85. Chien, W.-T.; Liang, C.-F.; Yu, C.-C.; Lin, J.-H.; Wu, H.-T.; Lin, C.-C. Adv. Synth. Catal. 2012, 354, 123.
86. Huang, X.; Barchi, J. J. Jr. Petite and Sweet: Glyco-Nanotechnology as a bridge to New Medicines, Chpater 2: Functionalized Glyconanoparticles for the Study of Glycobiology, American Chemical Society, Washington, DC, 2012.
87. (a) Ghosh, S. K.; Pal, T. Chem. Rev. 2007, 107, 4797; (b) Daniel, M.-C.; Astruc, D. Chem. Rev. 2004, 104, 293; (c) Baron, R.; Willner, B.; Willner, I. Chem. Commun. 2007, 323; (d) Katz, E.; Willner, I. Angew. Chem. Int. Ed. 2004, 43, 6042; (e) Rosi, N. L.; Mirkin, C. A. Chem. Rev. 2005, 105, 1547; (f) Storhoff, J. J.; Mirkin, C. A. Chem. Rev. 1999, 99, 1849; (g) Thaxton, C. S.; Georganopoulou, D. G.; Mirkin, C. A. Clin. Chim. Acta 2006, 363, 120; (h) Lu, Y.; Liu, J. Acc. Chem. Res. 2007, 40, 315; (i) Hu, M.; Chen, J.; Li, Z.; Au, L.; Hartland, G. V.; Li, X.; Marqueze, M.; Xia, Y. Chem. Soc. Rev. 2006, 35, 1084; (j) Sato, K.; Hosokawa, K.; Maeda, M.; Anal. Sci. 2007, 23, 17; (k) Pellegrino, T.; Kudera, S.; Liedl, T.; MuÇoz, J. A.; Manna, L.; Parak, W. J. Small 2005, 1, 48.
88. (a) Link, S.; El-Sayed, M. A. Annu. Rev. Phys. Chem. 2003, 54, 331; (b) Link, S.; El-Sayed, M. A. J. Phys. Chem. B 1999, 103, 8410.
89. Teichroeb, J. H.; Forrest, J. A.; Ngai, V.; Jones, L. W. Eur. Phys. J. E. 2006, 21, 19.
90. Aslan, K.; Lakowicz, J. R.; Geddes, C. D. Curr. Opin. Chem. Biol. 2005, 9, 538.
91. (a) Aroca, R. F.; Alvarez-Puebla, R. A.; Pieczonka, N.; Sanchez-Cortez, S.; Garcia-Ramos, J. V. Adv. Colloid. Interface. Sci. 2005, 116, 45; (b) Sha, M. Y.; Xu, H.; Penn, S. G.; Cromer, R. Nanomedicine 2007, 2, 725; (c) Kneipp, K.; Kneipp, H.; Kneipp, J. Acc. Chem. Res. 2006, 39, 443.
92. (a) Geddes, C. D.; Lakowicz, J. R.; J. Fluoresc. 2002, 12, 121; (b) Dubertret, B.; Calame, M.; Libchaber, A. J. Nat. Biotechnol. 2001, 19, 365; (c) Maxwell, D. J.; Taylor, J. R.; Nie, S. J. Am. Chem. Soc. 2002, 124, 9606.
93. (a) Authier, L.; Grossiord, C.; Brossier, P.; Limoges, B. Anal. Chem. 2001, 73, 4450; (b) Ozsoz, M.; Erdem, A.; Kerman, K.; Ozkan, D.; Tugrul, B.; Topcuoglu, N.; Ekren, H.; Talyan, M. Anal. Chem. 2003, 75, 2181; (c) Lévy, R.; Thanh, N. T. K.; Doty, R. C.; Hussain, I.; Nichols, R. J.; Schiffrin, D. J.; Brust, M.; Fernig, D. G. J. Am. Chem. Soc. 2004, 126, 10076.
94. (a) Nath, N.; Chilkoti, A. Anal. Chem. 2002, 74, 504; (b) Schultz, D. A. Curr. Opin. Biotechnol. 2003, 14, 13.
95. (a) Link, S.; El-Sayed, M. A.; J. Phys. Chem. B 1999, 103, 4212; Nikoobakht, B.; El-Sayed, M. A. Chem. Mater. 2003, 15, 1957; (b) Su, K. H.; Wei, Q. H.; Zhang, X.; Mock, J. J.; Smith, D. R.; Schultz, S. Nano Lett. 2003, 3, 1087.
96. Mirkin, C. A.; Lestinger, R. L.; Mucic, R. C. Nature 1996, 382, 607.
97. Otsuka, H.; Akiyama, Y.; Nagasaki, Y.; and Kataoka, K. J. Am. Chem. Soc. 2001, 123, 8226.
98. Thanh, N. T. K.; Rosenzweig, Z. Anal. Chem. 2002, 74, 1624.
99. Lin, S.; Liu, S.; Lin, C.; Chen, C. Anal. Chem. 2002, 74, 330.
100. Kim, Y.; Johnson, R. C.; Hupp, J. T. Nano Lett. 2001, 1, 165.
101. Daniel, W. L.; Han, M. S.; Lee, J.; Mirkin, C. A. J. Am. Chem. Soc. 2009, 131, 6362.
102. (a) Sönnichesn, C.; Reinhard, B. M.; Liphardt, J.; Alivisatos, A. P. Nat. Biotechnol. 2005, 23, 741; (b) Li, H.; Rothberg, L. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 14036; (c) Park, S. Y.; Lytton- Jean, A. K. R.; Lee, B.; Weigand, S.; Schatz, G. C.; Mirkin, C. A. Nature 2008, 451, 553; (d) Storhoff, J. J.; Lucas, A. D.; Garimella, V.; Bao, Y. P.; Muller, U. R. Nat. Biotechnol. 2004, 22, 883; (e) Medley, C. D.; Smith, J. E.; Tang, Z.; Wu, Y.; Bamrungsap, S.; Tan, W. Anal. Chem. 2008, 80, 1067; (f) Wang, Y. L.; Li, D.; Ren, W.; Liu, Z. J.; Dong, S. J.; Wang, E. K. Chem. Commun. 2008, 2520.
103. (a) De la Fuente, J. M.; Barrientos, A. G.; Rojas, T. C.; Rojo, J.; Cañada, J.; Fernández, A.; Penadés, S. Angew. Chem. Int. Ed. 2001, 40, 2257; (b) Liu, J.; Lu, Y. J. Am. Chem. Soc. 2003, 125, 6642; (c) Obare, S. O.; Hollowell, R. E.; Murphy, C. J. Langmuir 2002, 18, 10407; (d) Xue, X.; Wang, F.; Liu, X. G. J. Am. Chem. Soc. 2008, 130, 3244.
104. Elghanian, R.; Storhoff, J. J.; Mucic, R. C.; Letsinger, R. L.; Mirkin, C. A. Science 1997, 277, 1078.
105. Guarise, C.; Pasquato, L.; De Filippis, V.; Scrimin, P. Proc. Natl. Acad. Sci. USA 2006, 103, 3978.
106. Laromaine, A.; Koh, L.; Murugesan, M.; Ulijn, R. V.; Stevens, M. M. J. Am. Chem. Soc. 2007, 129, 4156.
107. Choi, Y.; Ho, N.-H.; Tung, C.-H. Angew. Chem. Int. Ed. 2007, 46, 707.
108. (a) Liu, R.; Liew, R.; Zhou, J.; Xing, B. Angew. Chem. Int. Ed. 2007, 46, 8799; (b) Jiang, T.; Liu, R.; Huang, X.; Feng, H.; Teo, W.; Xing, B.; Chem. Commun. 2009, 1972.
109. Wang, Z.; Lévy, R.; Fernig, D. G.; Brust, M. J. Am. Chem. Soc. 2006, 128, 2214.
110. (a) Oishi, J.; Asami, Y.; Mori, T.; Kang, J.-H.; Tanabe, M.; Niidome, T.; Katayama, Y. ChemBioChem 2007, 8, 875; (b) Gupta, S.; Andresen, H.; Stevens, M. M. Chem. Commun. 2011, 47, 2249.
111. Zhen, Z.; Tang, L.-J.; Long, H.; Jiang, J.-H. Anal. Chem. 2012, 84, 3614.
112. Nagahori, N.; Nishimura, S.-I. Chem. Eur. J. 2006, 12, 6478.
113. Laurent, S.; Forge, D.; Port, M.; Roch, A.; Robic, C.; Vander Elst, L.; Muller, R. Chem. Rev. 2008, 108, 2064.
114. (a) Gupta, A. K.; Gupta, M. Biomaterials 2005, 26, 3995. (b) Lee, H.; Yu, M. K.; Park, S.; Moon, S.; Min, J. J.; Jeong, Y. Y.; Kang, H.-W.; Jon, S. J. Am. Chem. Soc. 2007, 129, 12739. (c) Gu, H.; Ho, P.-L.; Tsang, K. W. T.; Wang, L.; Xu, B. J. Am. Chem. Soc. 2003, 125, 15702. (d) El-Boubbou, K.; Gruden, C.; Huang, X. J. Am. Chem. Soc. 2007, 129, 13392. (e) Chou, P.-H.; Chen, S.-H.; Liao, H.-K.; Lin, P.-C.; Her, G.-R.; Lai, A. C.-Y.; Chen, J.-H.; Lin, C.-C.; Chen, Y.-J. Anal. Chem. 2005, 77, 5990. (f) Lin, P.-C.; Chou, P.-H.; Chen, S.-H.; Liao, H.-K.; Wang, K.-Y.; Chen, Y.-J.; Lin, C.-C. Small 2006, 2, 485. (g) Wang, K.-Y.; Chuang, S.-A.; Lin, P.-C.; Huang, L.-S.; Chen, S.-H.; Ouarda, S.; Pan, W.-H.; Lee, P.-Y.; Lin, C.-C.; Chen, Y.-J. Anal. Chem. 2008, 80, 6159.
115. (a) Jin, M.-J.; Lee, D.-H. Angew. Chem. Int. Ed. 2010, 49, 1119. (b) Hu, A.; Yee, G. T.; Lin, W. J. Am. Chem. Soc. 2005, 127, 12486.
116. Basso, A.; Braiuca, P.; Cantone, S.; Ebert, C.; Linda, P.; Spizzo, P.; Caimi, P.; Hanefeld, U.; Degrassi, G.; Gardossia, L. Adv. Synth. Catal. 2007, 349, 877.
117. Iyer, S. S.; Anderson, A. S.; Reed, S.; Swanson, B.; Schmidt, J. G. Tetrahedron Lett. 2004, 45, 4285.
118. Wang, Q.; Graham, K.; Schauer, T.; Fietz, T.; Mohammed, A.; Liu, X.; Hoffend, J.; Haberkorn, U.; Eisenhut, M.; Mier, W. Nucl. Med. Biol. 2004, 31, 21.
119. Bruce, I. J.; Sen, T. Langmuir 2005, 21, 7029.
120. (a) Yu, H.; Huang, S.; Chokhawala, H.; Sun, M.; Zheng, H.; Chen, X. Angew. Chem. Int. Ed. 2006, 45, 3938. (b) Teo, C.-F.; Hwang, T.-S.; Chen, P.-H.; Hung, C.-H.; Gao, H.-S.; Chang, L.-S.; Lin, C.-H. Adv. Synth. Catal. 2005, 347, 967. (c) Izumi, M.; Shen, G.-J.; Wacowich-Sgarbi, S.; Nakatani, T.; Plettenburg, O.; Wong, C.-H. J. Am. Chem. Soc. 2001, 123, 10909. (d) Yu, H.; Chokhawala, H.; Karpel, R.; Yu, H.; Wu, B.; Zhang, J.; Zhang, Y.; Jia, Q.; Chen, X. J. Am. Chem. Soc. 2005, 127, 17618. (e) Yu, H.; Cheng, J.; Ding, L.; Khedri, Z.; Chen, Y.; Chin, S.; Lau, K.; Tiwari, V. K.; Chen, X. J. Am. Chem. Soc. 2009, 131, 18467.
121. Houseman, B. T.; Mrksich M. Angew. Chem. Int. Ed. 1999, 38, 782. (b) Chien, Y.-Y.; Jan, M.-D.; Adak, A. K.; Tzeng, H.-C.; Lin, Y.-P.; Chen, Y.-J.; Wang, K.-T.; Chen, C.-T.; Chen, C.-C.; Lin, C.-C. ChemBioChem 2008, 9, 1100.
122. Willis, L. M.; Gilbert, M.; Karwaski, M.-F.; Blanchard, M.-C.; Wakarchuk, W. W. Glycobiology 2008, 18, 177
123. Chiu, C. P. C.; Watts, A. G.; Lairson, L. L.; Gilbert, M.; Lim, D.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nat. Struct. Mol. Biol. 2004, 11, 163.
124. Morley, T. J.; Willis, L. M.; Whitfield, C.; Wakarchuk, W. W.; Withers, S. G. J. Biol. Chem. 2009, 284, 17404.
125. Stummeyer, K.; Dickmanns, A.; Mühlenhoff, M.; Gerardy-Schahn, R.; Ficner, R. Nat. Struct. Mol. Biol. 2005, 12, 90.
126. Frens, G. Nat. Phys. Sci. 1973, 241, 20.
127. (a) Jennings, H. J.; Roy, R.; Michon, F. J. Immunol. 1985, 134, 2651. (b) Bhattacharjee, A. K.; Jennings, H. J.; Kenny, C. P.; Martin, A.; Smith, I. C. P. J. Biol. Chem. 1975, 250, 1926. (c) Jennings, H. J.; Katzenellenbogen, E.; Lugowski, C.; Michon, F.; Roy, R.; Kasper, D. L. Pure Appl. Chem. 1984, 56, 893. (d) Gotschlich, E. C.; Fraser, B. A.; Nishimura, O.; Robbins, J. B.; Liu, T.-Y. J. Biol. Chem. 1981, 256, 8915.
128. Finne, J.; Leinonen, M.; Mäkelä, P. H. Lancet 1983, 2, 355.
129. Drake, P. M.; Nathan, J. K.; Stock, C. M.; Chang, P. V.; Muench, M. O.; Nakata, D.; Reader, J. R.; Gip, P.; Golden, K. P. K.; Weinhold, B.; Gerardy-Schahn, R.; Troy, F. A. II; Bertozzi C. R. J. Immunol. 2008, 181, 6850.
130. (a) Finne J. J. Biol. Chem. 1982, 257, 11966. (b) Röckle, I.; Seidenfaden, R.; Weinhold, B.; Mühlenhoff, M.; Gerardy-Schahn, R.; Hildebrandt, H. Dev. Neurobiol. 2008, 68, 1170. (c) Galuska, S. P.; Geyer, R.; Gerardy-Schahn, R.; Mühlenhoff, M.; Geyer H. J. Biol. Chem. 2008, 283, 17. (d) Hildebrandt, H.; Mühlenhoff, M.; Weinhold, B.; Gerardy-Schahn, R. J. Neurochem. 2007, 103, 56.
131. Rutishauser, U. J. Cell. Biochem. 1998, 70, 304.
132. (a) Rutishauser, U.; Acheson, A.; Hall, A. K.; Mann, D. M.; Sunshine, J. Science 1988, 240, 53. (b) Acheson, A.; Sunshine, J.; Rutishauser, U. J. Cell. Biol. 1991, 114, 143.
133. Muller, D.; Djebbara-Hannas, Z.; Jourdain, P.; Vutskits, L.; Durbec, P.; Rougon, G.; Kiss, J. Z. Proc. Natl. Acad. Sci. USA 2000, 97, 4315.
134. (a) Horstkorte, R.; Mühlenhoff, M.; Reutter, W.; Nöhring, S.; Zimmermann-Kordmann, M.; Gerardy-Schahn, R. Exp. Cell Res. 2004, 298, 268. (b) Seidenfaden, R.; Krauter, A.; Schertzinger, F.; Gerardy-Schahn, R.; Hildebrandt, H.; Mol. Cell. Biol. 2003, 23, 5908. (c) Moolenaar, C. E. C. K.; Muller, E. J.; Schol, D. J.; Figdor, C. G.; Bock, E.; Bitter-Suermann, D.; Michalides, R. J. A. M. Cancer Res. 1990, 50, 1102.
135. (a) Roth, J.; Zuber, C.; Wanger, P.; Taaties, D. J.; Weisgerber, C.; Heitz, P. U.; Goridis, C.; Bitter-Suermann, D. Proc. Natl. Acad. Sci. USA 1988, 85, 2999. (b) Figarella-Branger, D. F.; Durbec, P. L.; Rougon, G. N. Cancer Res. 1990, 50, 6364.
136. (a) Chu, K.-C.; Ren, C.-T.; Lu, C.-P.; Hsu, C.-H.; Sun, T.-H.; Han, J.-L.; Pal, B.; Chao, T.-A.; Lin, Y.-F.; Wu, S.-H.; Wong, C.-H.; Wu C.-Y. Angew. Chem. Int. Ed. 2011, 50, 9391. (b) Liang, C.-F.; Yan, M.-C.; Chang, T.-C.; Lin, C.-C. J. Am. Chem. Soc. 2009, 131, 3138. (c) Tanaka, H.; Nishiura, Y.; Takahashi, T. J. Org. Chem. 2009, 74, 4383. (d) 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.
137. (a) Boons, G. J.; Demchenko, A. V.; Chem. Rev. 2000, 100, 4539. (b) Kiefel, M. J.; von Itzstein, M. Chem. Rev. 2002, 102, 471.
138. Cho, J.-W.; Troy, F. A. II Proc. Natl. Acad. Sci. USA 1994, 91, 11427.
139. Frosch, M.; Weisgerber, C.; Meyer, T. F. Proc. Natl. Acad. Sci. USA 1989, 86, 1669.
140. (Kojima, N.; Tachida, Y.; Yoshida, Y.; Tsuji, S. J. Biol. Chem. 1996, 271, 19457.
141. (a) Mühlenhoff, M.; Eckhardt, M.; Bethe, A.; Frosch, M.; Gerardy-Schahn, R. Curr. Biol. 1996, 6, 1188. (b) Eckhardt, M.; Gerardy-Schahn, R. Glycobiology 1998, 8, 1165.
142. Steenbergen, S. M.; Vimr, E. R. J. Biol. Chem. 2003, 278, 15349.
143. Ferrero, M. A.; Luengo, J. M.; Reglero, A. Biochem. J. 1991, 280, 575.
144. Steenbergen, S. M.; Vimr E. R. Mol. Microbiol. 1990, 4, 603.
145. McGowen, M. M.; Vionnet, J.; Vann, W. F. Glycobiology 2001, 11, 613.
146. (a) Bloom, J. D.; Meyer, M. M.; Meinhold, P.; Otey, C. R.; MacMillan, D.; Arnold, F. H. Curr. Opin. Struct. Biol. 2005, 15, 447. (b) Dalby, P. A. Curr. Opin. Struct. Biol. 2011, 21, 473. (c) Turner, N. J. Trends Biotechnol. 2003, 21, 474.
147. Goddard, J. P.; Reymond, J. L. Curr. Opin. Biotechnol. 2004, 15, 314.
148. (a) Kittl, R.; Withers, S. G.; Carbohydr. Res. 2010, 345, 1272. (b) Kwan, D. H.; Withers, S. G. J. Carbohydr. Chem. 2011, 30, 181.
149. Lin, H.; Tao, H.; Cornish, V. W. J. Am. Chem. Soc. 2004, 126, 15051.
150. (a) Aharoni, A.; Thieme, K.; Chiu, C. P. C.; Buchini, S.; Lairson, L. L.; Chen, H.; Strynadka, N. C. J.; Wakarchuk, W. W.; Withers, S. G. Nat. Method 2006, 3, 609. (b) Yang, G.; Rich, J. R.; Gilbert, M.; Wakarchuk, W. W.; Feng, Y.; Withers, S. G. J. Am. Chem. Soc. 2010, 132, 10570.
151. Williams, G. J.; Zhang, C.; Thorson, J. S. Nat. Chem. Biol. 2007, 3, 657.
152. (a) Hancock, S. M.; Tarling, C. A.; Withers, S. G. Anal. Biochem. 2008, 382, 48. (b) Hancock, S. M.; Rich, J. R.; Caines, M. E. C.; Strynadka, N. C. J.; Withers, S. G. Nat. Chem. Biol. 2009, 5, 508.
153. Kim, Y.-W.; Lee, S. S.; Warren, R. A. J.; Withers, S. G. J. Biol. Chem. 2004, 279, 42787.
154. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
155. Li, N.; Binder, W. H. J. Mater. Chem. 2011, 21, 16717.
156. Iha, R. K.; Wooley, K. L.; Nyström, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620.
157. Mehta, S.; Gilbert, M.; Wakarchuk, W. W.; Whitfield, D. M. Org. Lett. 2000, 2, 751.
158. (a) Gilbert, M.; Brisson, J.-R.; Karwaski, M.-F.; Michniewicz, J.; Cunningham, A.-M.; Wu, Y.; Young, N. M.; Wakarchuk, W. W. J. Biol. Chem. 2000, 275, 3896. (b) Lee, H. J.; Lairson, L. L.; Rich, J. R.; Lameignere, E.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. J. Biol. Chem. 2011, 286, 35922.
159. del Amo, D. S.; Wang, W.; Jiang, H.; Besanceney, C.; Yan, A. C.; Levy, M.; Liu, Y.; Marlow, F. L.; Wu, P. J. Am. Chem. Soc. 2010, 132, 16893.
160. Blixt, O.; Vasiliu, D.; Allin, K.; Jacobsen, N.; Warnock, D.; Razi, N.; Paulson, J. C.; Bernatchez, S.; Gilbert, M.; Wakarchuk, W. W. Carbohydr. Res. 2005, 340, 1963.

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