Journal of the American Chemical Society
Article
Surowitz, K. G.; Maddon, P. J.; Heston, W. D. W.; Olson, W. C. Proc.
Natl. Acad. Sci. U.S.A. 2003, 100, 12590.
Scheme 4
(5) Ghosh, A.; Heston, W. D. W. J. Cell. Biochem. 2004, 91, 528.
(6) Kiessling, A.; Fussel, S.; Wehner, R.; Bachmann, M.; Wirth, M. P.;
̈
Rieber, E. P.; Schmitz, M. Eur. Urol. 2008, 53, 694.
(7) Chang, S. S.; Reuter, V. E.; Heston, W. D. W.; Bander, N. H.;
Grauer, L. S.; Gaudin, P. B. Cancer Res. 1999, 59, 3192.
(8) (a) Dubrovska, A.; Kim, C.; Elliott, J.; Shen, W.; Kuo, T.-H.; Koo,
D.-I.; Li, C.; Tuntland, T.; Chang, J.; Groessl, T.; Wu, X.; Gorney, V.;
Ramirez-Montagut, T.; Spiegel, D. A.; Cho, C. Y.; Schultz, P. G. ACS
Chem. Biol. 2011, 6, 1223. (b) Murelli, R. P.; Zhang, A. X.; Michel, J.;
Jorgensen, W. L.; Spiegel, D. A. J. Am. Chem. Soc. 2009, 131, 17090.
(c) Kozikowski, A. P.; Zhang, J.; Nan, F.; Petukhov, P. A.; Grajkowska,
E.; Wroblewski, J. T.; Yamamoto, T.; Bzdega, T.; Wroblewska, B.;
Neale, J. H. J. Med. Chem. 2004, 47, 1729. (d) Kularatne, S. A.; Wang,
K.; Santhapuram, H.-K. R.; Low, P. S. Mol. Pharmaceutics 2009, 6, 780.
(9) (a) Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.;
Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. J. Am.
Chem. Soc. 1998, 120, 12474. (b) Ragupathi, G.; Koide, F.; Livingston,
P. O.; Cho, Y. S.; Endo, A.; Wan, Q.; Spassova, M. K.; Keding, S. J.;
Allen, J.; Ouerfelli, O.; Wilson, R. M.; Danishefsky, S. J. J. Am. Chem.
Soc. 2006, 128, 2715. (c) Zhu, J.; Wan, Q.; Lee, D.; Yang, G.;
Spassova, M. K.; Ouerfelli, O.; Ragupathi, G.; Damani, P.; Livingston,
P. O.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 9298.
(10) Holmes, E. H.; Greene, T. G.; Tino, W. T.; Boynton, A. L.;
Aldape, H. C.; Misrock, S. L.; Murphy, G. P. Prostate Suppl. 1996, 7,
25.
(11) Davis, M. I.; Bennett, M. J.; Thomas, L. M.; Bjorkman, P. J. Proc.
Natl. Acad. Sci. U.S.A. 2005, 102, 5981.
̌
́ ́ ̌ ̌
(12) Barinka, C.; Sacha, P.; Sklenar, J.; Man, P.; Bezouska, K.;
Slusher, B. S.; Konvalinka, J. Protein Sci. 2004, 13, 1627.
(13) Schauer, R. Curr. Opin. Struct. Biol. 2009, 19, 507.
(14) Courtney, A. H.; Puffer, E. B.; Pontrello, J. K.; Yang, Z.-Q.;
Kiessling, L. L. Proc. Natl. Acad. Sci. 2009, 106, 2500.
(15) Wang, P.; Zhu, J.; Yuan, Y.; Danishefsky, S. J. J. Am. Chem. Soc.
2009, 131, 16669.
a
Reagents and Conditions: (a) NaOMe/NaOH, MeOH/H2O, rt, 20
h; (b) 1,2-ethylenediamine, n-BuOH, PhMe, 90 °C, 24 h; (c) Ac2O,
Et3N, MeOH, rt; (d) Na/NH3, THF, −78 °C, 11−25% (over 4 steps).
(16) (a) Hard, K.; Mekking, A.; Damm, J. B. L.; Kamerling, J. P.; De
̊
Boer, W.; Wijnands, R. A.; Vliegenthart, J. F. G. Eur. J. Biochem. 1990,
193, 263. (b) Sakai, H.; Yamagishi, F.; Miura, M.; Hata, K.; Koyama, I.;
Sakagishi, Y.; Komoda, T. Tumor Biol. 1995, 15, 230. (c) Ishii, K.;
Iwasaki, M.; Inoue, S.; Kenny, P. T.; Komura, H.; Inoue, Y. J. Biol.
Chem. 1989, 264, 1623.
(17) (a) Unverzagt, C. Chem.Eur. J. 2003, 9, 1369. (b) Nagorny,
P.; Fasching, B.; Li, X.; Chen, G.; Aussedat, B.; Danishefsky, S. J. J. Am.
Chem. Soc. 2009, 131, 5792.
ASSOCIATED CONTENT
* Supporting Information
General experimental procedures, including spectroscopic and
analytical data for new compounds. This material is available
■
S
AUTHOR INFORMATION
Corresponding Author
■
(18) Dinkelaar, J.; Duivenvoorden, B. A.; Wennekes, T.; Overkleeft,
H. S.; Boot, R. G.; Aerts, J. M. F. G.; Codee
A. Eur. J. Org. Chem. 2010, 2010, 2565.
́
, J. D. C.; van der Marel, G.
(19) (a) Crich, D. Acc. Chem. Res. 2010, 43, 1144. (b) Crich, D.; Sun,
S. J. Org. Chem. 1996, 61, 4506.
(20) Crich, D.; Li, H.; Yao, Q.; Wink, D. J.; Sommer, R. D.;
Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 5826.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
(21) Sjolin, P.; Kihlberg, J. J. Org. Chem. 2001, 66, 2957.
̈
Support for this research was provided by the National Institute
of Health (CA103823 to S.J.D.). M.A.W. would like to
acknowledge Terrie Brodeur Breast Cancer Foundation for
postdoctoral fellowship. We also thank Dr. George Sukenick,
Hui Fang, and Sylvi Rusli of SKI’s NMR core facility for mass
spectral and NMR assistance.
(22) (a) Dudkin, V. Y.; Miller, J. S.; Dudkina, A. S.; Antczak, C.;
Scheinberg, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130,
13598. (b) Dudkin, V. Y.; Miller, J. S.; Danishefsky, S. J. J. Am. Chem.
Soc. 2003, 126, 736.
(23) Wu, B.; Hua, Z.; Warren, J. D.; Ranganathan, K.; Wan, Q.;
Chen, G.; Tan, Z.; Chen, J.; Endo, A.; Danishefsky, S. J. Tetrahedron
Lett. 2006, 47, 5577.
(24) (a) Marra, A.; Mallet, J.-M.; Amatore, C.; Sinay, P. Synlett 1990,
̈
REFERENCES
(1) Roth, J. Chem. Rev. 2002, 102, 285.
(2) Montreuil, J.; Vliegenthart, J. F. G.; (Eds.), H. S., Glycoproteins
and Disease. Elsevier Science: 1996.
(3) (a) Danishefsky, S. J.; Allen, J. R. Angew. Chem., Int. Ed. 2000, 39,
836. (b) Zhu, J.; Warren, J. D.; Danishefsky, S. J. Expert Rev. Vaccines
2009, 8, 1399.
■
1990, 572. (b) Zhang, Y.-M.; Mallet, J.-M.; Sinay, P. Carbohydr. Res.
̈
1992, 236, 73.
(25) Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269.
(26) Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O.
Carbohydr. Res. 1993, 243, 139.
(4) Schulke, N.; Varlamova, O. A.; Donovan, G. P.; Ma, D.; Gardner,
̈
J. P.; Morrissey, D. M.; Arrigale, R. R.; Zhan, C.; Chodera, A. J.;
16433
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