PAPER
Synthesis of Fluorescein-Labelled GalNAca1-O-Ser/Thr (Tn) Glycopeptides
769
Glycosylated building blocks were pre-activated before placement
in the synthesizer. The glycosylated building block (1.5 equiv) was
dissolved in DMF, HOAt (1.5 equiv), and HATU (1.45 equiv) were
then added and the mixture shaken until dissolved. The soln was
transferred to the reaction vessel, followed by the addition of colli-
dine (4.5 equiv). The mixture was subjected to microwave irradia-
tion at 80 °C for 20 min, and a sample of the resin (1.0 mg) was
taken for the Kaiser test.
(10) Cambi, A.; Figdor, C. G. Curr. Opin. Cell Biol. 2003, 15,
539.
(11) Cambi, A.; Koopman, M.; Figdor, C. G. Cell Microbiol.
2005, 7, 481.
(12) Van Gisbergen, K. P.; Aarnoudse, C. A.; Meijer, G. A.;
Geijtenbeek, T. B.; van Kooyk, Y. Cancer Res. 2005, 65,
5935.
(13) Napoletano, C.; Rughetti, A.; Agervig Tarp, A. P.; Coleman,
J.; Bennett, E. P.; Picco, G.; Sale, P.; Denda-Nagai, K.;
Irimura, T.; Mandel, U.; Clausen, H.; Frati, L.; Taylor-
Papadimitriou, J.; Burchell, J.; Nuti, M. Cancer Res. 2007,
e
Removal of the Dde protecting group (d) from the N -amino group
of the lysine residue was performed manually using 2% hydrazine
hydrate soln in DMF (2 × 3 min).
67, 8358.
(14) For a review see: Gamblin, D. P.; Scanlan, E. M.; Davis, B.
G. Chem. Rev. 2009, 109, 131.
Supporting Information for this article is available online at
http://www.thieme-connect.com/ejournals/toc/synthesis.
(
15) (a) Hollosi, M.; Kollat, E.; Laczko, I. K.; Medzihradszky, F.;
Thurin, J.; Otvos, L. Tetrahedron Lett. 1991, 32, 1531.
(
b) Paulsen, H.; Schleyer, A.; Mathieux, N.; Meldal, M.;
Bock, K. J. Chem. Soc., Perkin Trans. 1 1997, 281.
c) Paulsen, H.; Schleyer, A.; Mathieux, N.; Meldal, M.;
Bock, K. J. Chem. Soc., Perkin Trans. 1 1997, 281.
d) Andrews, D. M.; Seale, P. W. Int. J. Pept. Protein Res.
993, 42, 165.
Acknowledgment
(
We thank the Maurice Wilkins Centre for Molecular Biodiscovery
for financial support.
(
1
(
16) (a) Matsushita, T.; Hinou, H.; Fumoto, M.; Kurogochi, M.;
Fujitani, N.; Shimizu, H.; Nishimura, S. I. J. Org. Chem.
2006, 71, 3051. (b) Matsushita, T.; Hinou, H.; Kurogochi,
M.; Shimizu, H.; Nishimura, S. I. Org. Lett. 2005, 7, 877.
References
(
1) (a) Strous, G. J.; Dekker, J. Crit. Rev. Biochem. Mol. Biol.
992, 27, 57. (b) Hang, H. C.; Bertozzi, C. R. Bioorg. Med.
1
Chem. 2005, 13, 5021. (c) Fumoto, M.; Hinou, H.; Ohta, T.;
Ito, T.; Yamada, K.; Takimoto, A.; Kondo, H.; Shimizu, H.;
Inazu, T.; Nakahara, Y.; Nishimura, S.-I. J. Am. Chem. Soc.
(17) Kowalczyk, R.; Harris, P. W. R.; Dunbar, R. P.; Brimble, M.
A. Synthesis 2009, 2210.
(18) Carpino, L.; Han, G. J. Org. Chem. 1972, 37, 3404.
(19) Fillian, D.; Deraeet, M.; Holleran, B. J.; Escher, E. J. Med.
Chem. 2006, 49, 2200.
2005, 127, 11804.
(
2) (a) Dwek, R. A. Chem. Rev. 1996, 96, 683. (b) Hanisch,
F.-G.; Muller, S. Glycobiology 2000, 10, 439.
3) (a) Davis, B. G. Chem. Rev. 2002, 102, 579. (b) Watt, G.
M.; Lund, J.; Levens, M.; Kolli, V. S. K.; Jefferis, R.; Boons,
G.-J. Chem. Biol. 2003, 10, 807. (c) Lui, H.; Wang, L.;
Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc.
(20) Taylor, C.; Weir, C.; Jorgensen, C. Aust. J. Chem. 2002, 55,
(
135.
(21) Vegad, H.; Gray, C.; Somers, P.; Dutta, A. J. Chem. Soc.,
Perkin Trans. 1 1997, 9, 1429.
(22) Payne, R. J.; Ficht, S.; Tang, S.; Brik, A.; Yang, Y.-Y.; Case,
D. A.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 13527.
(23) Vuljanic, T.; Bergquist, K.-E.; Clausen, H.; Roy, S.;
Kihlberg, J. Tetrahedron 1996, 52, 7983.
(24) (a) Macmillan, D.; Bertozzi, C. R. Angew. Chem. Int. Ed.
2004, 43, 1355. (b) Winans, K. A.; King, D. S.; Rao, V. R.;
Bertozzi, C. R. Biochemistry 1999, 38, 11700.
(25) Fara, M. A.; Diaz-Mochon, J. J.; Bradley, M. Tetrahedron
Lett. 2006, 47, 1011.
(26) Fischer, R.; Mader, O.; Jung, G.; Brock, R. Bioconjugate
Chem. 2003, 14, 653.
2003, 125, 1702. (d) Gamblin, D. P.; Garnier, P.;
van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B.
G. Angew. Chem. Int. Ed. 2004, 43, 828. (e) Davis, B. G.
Science 2004, 303, 480. (f) Dube, D. H.; Bertozzi, C. R. Nat.
Rev. Drug Discovery 2005, 4, 477.
(
4) Gendler, S. J.; Spicer, A. P.; Lalani, E. N. Am. Rev. Respir.
Dis. 1991, 144, S42.
(
5) (a) Hanisch, F. G. Biol. Chem. 2001, 382, 143. (b)Burchell,
J. M.; Mungal, A.; Taylor-Papadimitriou, J. J. Mammary
Gland Biol. Neoplasia 2001, 6, 355.
(
6) Buskas, T.; Thompson, P.; Boons, G.-J. Chem. Commun.
(27) Tai, C.-A.; Kulkarni, S. S.; Hung, S.-C. J. Org. Chem. 2003,
2009, 5335.
68, 8719.
(
(
(
7) Mellman, I.; Steinman, R. M. Cell 2001, 106, 255.
8) Bevan, M. J. J. Exp. Med. 1976, 143, 1283.
9) Banchereau, J.; Steinman, R. M. Nature 1998, 392, 245.
(28) Bukowski, R.; Morris, L. M.; Woods, R. J.; Weimar, T. Eur.
J. Org. Chem. 2001, 2697.
(29) Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57,
1244.
Synthesis 2010, No. 5, 763–769 © Thieme Stuttgart · New York