J. Auernheimer, H. Kessler / Bioorg. Med. Chem. Lett. 16 (2006) 271–273
273
Furthermore, the cell adhesion is specific to the RGD-
peptide and not to the anchor, because the control
conjugate 9, containing the RbAD-sequence, showed
no enhanced cell adhesion. Another benefit of the new
anchor building block is that only one lysine is required
for branching. A second lysine generation, leading to an
octameric anchor, showed no effect on cell adhesion.
5. Pfaff, M.; Tangemann, K.; M u¨ ller, B.; Gurrath, M.;
M u¨ ller, G.; Kessler, H.; Timpl, R.; Engel, J. J. Biol. Chem.
1
994, 269, 20233.
6
. (a) Wayner, E. A.; Orlando, R. A.; Cheresh, D. A. J. Cell
Biol. 1991, 113, 919; (b) Leavesley, D. I.; Ferguson, G. D.;
Wayner, E. A.; Cheresh, D. A. J. Cell Biol. 1992, 117(5),
1
101.
7
. (a) Schliephake, H.; Scharnweber, D.; Dard, M.; R o¨ ßler,
S.; Sewing, A.; Meyer, J.; Hoogestraat, D. Clin. Oral
Implants Res. 2002, 13, 312; (b) Elmengaard, B.; Bechtold,
J. E.; Søballe, K. Biomaterials 2005, 26, 3521; (c) Stein-
hauser, E.; Liebend o¨ rfer, A.; Enderle, A.; Bader, R.;
Kerschbaumer, S.; Brill, T.; Busch, R.; Gradinger, R. MP
Materialpr u¨ fung 2005, 47(4), 197.
In conclusion, the synthesis of a benzylprotected bis-
phosphonic acid was developed. This allows the syn-
thesis of peptides for anchoring on titanium, with
standard Fmoc-strategy. The cleavage of benzylesters
occurs under the usual deprotection conditions with
TFA.
8
9
. Auernheimer, J.; Zukowski, D.; Dahmen, C.; Kantlehner,
M.; Enderle, A.; Goodman, S.L.; Kessler, H. ChemBio-
Chem 2005, in press.
. Rensing, S.; Arendt, M.; Springer, A.; Grawe, T.;
Schrader, T. J. Org. Chem. 2001, 66, 5814.
Acknowledgments
1
0. Saady, M.; Lebeau, L.; Mioskowski, C. Helv. Chim. Acta
995, 78, 670.
1. ESI-MS m/z = 671.3 [m+H] , 693.3 [m+Na] , 1340.9
1
The authors thank Dr. Anja Enderle (Biomet Deutsch-
land GmbH) for performing the cell adhesion assay.
The help in synthesis from Irina Wasilewitsch and Anne
Wolter is gratefully acknowledged.
+
+
1
+
+
1
[2m+H] , 1363.0 [2m+Na] .
H
NMR (DMSO,
5
00 MHz): d (ppm) = 7.80 (2H, s), 7.26 (1H, s), 7.31–7.27
20H, m), 4.94 (8H, m), 3.37 (4H, dd, J = 5.6, 21.6 Hz).
(
2. (a) Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.;
Sotiriu, P.; Weqing, Y.; Sch a¨ ffer, W. Tetrahedron Lett.
1
1
References and notes
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3. 1 equiv anchor, 1.1 equiv HOAt, 0.97 equiv HATU, and
0 equiv collidine in 2 mL DMF activation for 2 h
1
followed by addition of 1 equiv cyclo(-R(Pbf)GD(Ot-
Bu)fK-). Precipitation in water after 24 h.
1
1
1
4. Colum: YMC-ODS-A 120 5-C18 (5 lm, 250 mm ·
2
with 0.1% TFA.
2
0 mm); gradient: 10–60% MeCN in H O in 30 min. Both
1
996, 118, 7461.
4
. Kantlehner, M.; Schaffner, P.; Finsinger, D.; Meyer, J.;
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1
07.
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