directed and combinatorial synthesis of carbohydrates or other
bioorganic molecules as well as biological screening thereof.
Considering the manipulative character of STICS strategy,
further automation can be envisaged, and is under pursuit in
our laboratories.
18 X. Huang, L. Huang, H. Wang and X. S. Ye, Angew. Chem., Int.
Ed., 2004, 43, 5221–5224.
19 Z. Zhang, I. R. Ollmann, X. S. Ye, R. Wischnat, T. Baasov and
C. H. Wong, J. Am. Chem. Soc., 1999, 121, 734–753.
20 P. H. Seeberger and D. B. Werz, Nat. Rev. Drug Discovery, 2005, 4,
751–763.
21 D. B. Werz, B. Castagner and P. H. Seeberger, J. Am. Chem. Soc.,
2007, 129, 2770–2771.
22 F. R. Carrel, K. Geyer, J. D. C. Codee and P. H. Seeberger, Org.
´
Lett., 2007, 9, 2285–2288.
23 P. H. Seeberger and W. C. Haase, Chem. Rev., 2000, 100,
4349–4393.
The authors thank NIGMS (GM072693) and NSF
(CHE-0547566) for financial support of this work. Dr R. E. K.
Winter and Mr J. Kramer (UM – St. Louis) are thanked for
HRMS determinations.
24 N. K. Kochetkov, Russ. Chem. Rev., 2000, 69, 795–820.
25 M. Mrksich, Chem. Soc. Rev., 2000, 243, 267–273, and references
therein.
Notes and references
1 A. Varki, Glycobiology, 1993, 3, 97–130.
2 P. M. Rudd, T. Elliott, P. Cresswell, I. A. Wilson and R. A. Dwek,
Science, 2001, 291, 2370–2376.
3 C. R. Bertozzi and L. L. Kiessling, Science, 2001, 291,
2357–2364.
26 J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo and
G. M. Whitesides, Chem. Rev., 2005, 105, 1103–1169.
27 O. V. Shulga, K. Jefferson, A. R. Khan, V. T. D’Souza, J. Liu,
A. V. Demchenko and K. J. Stine, Chem. Mater., 2007, 19,
3902–3911.
4 J. A. Prescher and C. R. Bertozzi, Nat. Chem. Biol., 2005, 1, 13–21.
5 K. C. Nicolaou and H. J. Mitchell, Angew. Chem., Int. Ed., 2001,
40, 1576–1624.
6 S. Manabe and Y. Ito, J. Am. Chem. Soc., 2002, 124, 12638–12639.
7 J. Lu, K. N. Jayaprakash, U. Schlueter and B. Fraser-Reid, J. Am.
Chem. Soc., 2004, 126, 7540–7547.
28 H. Lonn, J. Carbohydr. Chem., 1987, 6, 301–306.
29 R. Verduyn, M. Douwes, P. A. M. van der Klein, E. M. Mosinger,
¨
G. A. van der Marel and J. H. van Boom, Tetrahedron, 1993, 49,
7301–7316.
30 P. Pornsuriyasak and A. V. Demchenko, Chem.–Eur. J., 2006, 12,
6630–6646.
8 D. Crich, A. Banerjee and Q. Yao, J. Am. Chem. Soc., 2004, 126,
14930–14934.
31 M. N. Kamat, N. P. Rath and A. V. Demchenko, J. Org. Chem.,
2007, 72, 6938–6946.
9 J. D. C. Code
´
e, B. Stubba, M. Schiattarella, H. S. Overkleeft, C. A.
32 C.-J. Zhong, R. C. Brush, J. Anderegg and M. D. Porter,
Langmuir, 1999, 15, 518–525.
33 J. Noh, H. S. Kato, M. Kawai and M. Hara, J. Phys. Chem. B,
2002, 106, 13268–13272.
34 M. A. Fox, J. K. Whitesell and A. J. McKerrow, Langmuir, 1998,
14, 816–820.
35 K. W. Kittredge, M. A. Minton, M. A. Fox and J. K. Whitesell,
Helv. Chim. Acta, 2002, 85, 788–798.
36 J.-S. Park, A. N. Vo, D. Barriet, Y.-S. Shon and T. R. Lee,
Langmuir, 2005, 21, 2902–2911.
37 T. M. Willey, A. L. Vance, C. Bostedt, T. van Buuren,
R. W. Meulenberg, L. J. Terminello and C. S. Fadley, Langmuir,
2004, 20, 4939–4944.
A. van Boeckel, J. H. van Boom and G. A. van der Marel, J. Am.
Chem. Soc., 2005, 127, 3767–3773.
10 J. H. Kim, H. Yang, J. Park and G. J. Boons, J. Am. Chem. Soc.,
2005, 127, 12090.
11 G. Ragupathi, F. Koide, P. O. Livingston, Y. S. Cho, A. Endo,
Q. Wan, M. K. Spassova, S. J. Keding, J. Allen, O. Ouerfelli,
R. M. Wilson and S. J. Danishefsky, J. Am. Chem. Soc., 2006, 128,
2715–2725.
12 D. P. Galonic and D. Y. Gin, Nature, 2007, 446, 1000–1007.
13 P. H. Seeberger and D. B. Werz, Nature, 2007, 446, 1046–1051.
14 M. Joe, Y. Bai, R. C. Nacario and T. L. Lowary, J. Am. Chem.
Soc., 2007, 129, 9885–9901.
15 T. Polat and C. H. Wong, J. Am. Chem. Soc., 2007, 129,
12795–12800.
16 Y. Wang, X. S. Ye and L. H. Zhang, Org. Biomol. Chem., 2007, 5,
2189–2200.
17 C. C. Wang, J. C. Lee, S. Y. Luo, S. S. Kulkarni, Y. W. Huang,
C. C. Lee, K. L. Chang and S. C. Hung, Nature, 2007, 446,
896–899.
38 R. Karamanska, B. Mukhopadhyay, D. A. Russell and
R. A. Field, Chem. Commun., 2005, 3334–3336.
39 E. U. Thoden van Velzen, J. F. J. Engbersen, P. J. De Lange, J. W.
G. Mahy and D. N. Reinhoudt, J. Am. Chem. Soc., 1995, 117,
6853–6862.
40 M. C. Parlato, M. N. Kamat, H. Wang, K. J. Stine and
A. V. Demchenko, J. Org. Chem., 2008, 73, 1716–1725.
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1836 | Chem. Commun., 2009, 1834–1836