T. Ziegler et al. / Tetrahedron: Asymmetry 13 (2002) 911–914
913
Scheme 4. Reagents and conditions: (i) Piperidine, DMF, 25°C, 0.75 h, 92% 15. (ii) Reaction cycles, 54% 16.
AM,16 Rink-amid-MBHA,17 and Wang-Ala-Fmoc18
(14) resins, respectively, was also conducted and used
for constructing a neoglycopeptide library containing
256 compounds as follows. The four different glycosyl
amino acid moieties 8a–c, and 11 were coupled with
polymer supported Wang-Ala resin 15 as shown in
Scheme 4 using the split/mix technology. The progress
of the couplings was monitored by MAS–NMR spec-
troscopy. After final removal of the library from the
resin, compounds 16 were obtained in pure form as
determined by LC in 54% overall yield and character-
ized by inspecting significant regions of their 13C NMR
spectra19 and by ESI mass spectrometry. All other
compounds described here were fully characterized by
NMR, specific rotation, and elemental analysis,
respectively.
3. (a) Suhara, Y.; Ichikawa, M.; Hildreth, J. E. K.;
Ichikawa, Y. Tetrahedron Lett. 1996, 37, 2549–2552; (b)
Suhara, Y.; Hildreth, J. E. K.; Ichikawa, Y. Tetrahedron
Lett. 1996, 37, 1575–1578.
4. Goodnow, R. A.; Tam, S.; Pruess, D. L.; McComas, W.
W. Tetrahedron Lett. 1997, 38, 3199–3202.
5. (a) Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.;
Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu,
S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem.
Soc. 1996, 118, 6826–6840; (b) Lampe, T. F. J.; Weitz-
Schmidt, G.; Wong, C.-H. Angew. Chem., Int. Ed. 1998,
37, 1707–1711.
6. (a) St. Hilaire, P. M.; Lowary, T. L.; Meldal, M.; Bock,
K. J. Am. Chem. Soc. 1998, 120, 13312–13320; (b) Chris-
tensen, M. K.; Meldal, M.; Bock, K.; Cordes, H.;
Mouritsen, S.; Elsner, H. J. Chem. Soc., Perkin Trans. 1
1994, 1299–1310.
7. Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39,
1621–1624.
Acknowledgements
8. Kutterer, K. M. K.; Barnes, M. L.; Arya, P. J. Comb.
Chem. 1999, 1, 28–31.
We thank Dr. H. Schmickler, I. Hoven, and C.
Schmitz, University of Cologne, for performing the
NMR spectra and the elemental analyses. This work
was finanicially supported by the Deutsche Forschungs-
gemeinschaft, and by the Fonds der Chemischen
Industrie.
9. (a) Eckhardt, E.; Ziegler, T. Carbohydr. Res. 1994, 264,
253–269; (b) Ziegler, T. Carbohydr. Res. 1994, 262, 195–
212.
10. Sasaki, A.; Murahashi, N.; Yamada, H.; Morikawa, A.
Biol. Pharm. Bull. 1995, 18, 740–746.
11. Ibatullin, F. M.; Shabolin, K. A. Synth. Commun. 2000,
30, 2819–2824.
12. Boxus, T.; Touillaux, R.; Dive, G.; Marchand-Brynaert,
References
J. Bioorg. Med. Chem. 1998, 6, 1577–1593.
13. Wang, J.-Q.; Chen, Xi.; Zhang, W.; Zacharek, S.; Chen,
Y.; Wang, P. G. J. Am. Chem. Soc. 1999, 121, 8174–8181.
14. (a) Klausner, Y. S.; Bodansky, M. Synthesis 1971, 453–
463; (b) Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968,
90, 1651–1652; (c) Dourtoglau, V.; Gross, B. Synthesis
1984, 572–574; (d) Sheehan, J. C.; Preston, M. J. Am.
Chem. Soc. 1965, 87, 2492–2493.
1. For reviews on glycopeptide synthesis, see: (a) Davis, B.
G. Chem. Rev. 2002, 102, 579–601; (b) Elmore, D. T.
Amino Acids Peptides Proteins 2001, 32, 107–162; (c) St.
Hilaire, P. M.; Meldal, M. Comb. Chem. 1999, 291–318;
(d) Fuchs, E. F.; Lehmann, J. Carbohydr. Res. 1976, 49,
267–273.
2. Nicolaou, K. C.; Flo¨rke, H.; Egan, M. G.; Barth, T.;
Estevez, V. A. Tetrahedron Lett. 1995, 36, 1775–1778.
15. The calculation for compound 13 was performed with the
program MacroModel 6.5 using a workstation O2 (Sili-