Abstract
A rapid method is reported for the preparation of biotinylated 4-amino-D-phenylalanine(D-Aph) with Fmoc as the protecting group at the α-amino. Different coupling reagents and conditions were studied to get the biotinylated compound. Coupling reagents like 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophos-phate and BOP were found to be very efficient. Biotinylated Boc-L-Aph and biotinylated Fmoc-L-lysine were also successfully prepared by this method.
Keywords
References
1.
Russell-Jones G.J.
,
Westwood S. W.
,
Farnworth P. G.
,
Findlay J. K.
, and
Burger H. G.
, Bioconjug. Chem. , 1995 , 6 , 34 .
2.
Russell-Jones G.J.
,
Westwood S. W.
, and
Habberfield A. D.
, Proc. Int. Symp. Control. Release Bioact. Mater. , 1996 , 23 , 49 .
3.
Chalasani K.B.
,
Russell-Jones G. J.
,
Yandrapu S. K.
,
Diwan P. V.
, and
Jain S. K.
, J. Control Rel. , 2007 , 117 , 421 .
4.
Francis M.F.
,
Cristea M.
, and
Winnik F. M.
, Biomacromol. , 2005 , 6 , 2462 .
5.
Youn Y.S.
,
Chae S. Y.
,
Lee S.
,
Kwon M. J.
,
Shin H. J.
, and
Lee K. C.
, Eur. J. Pharm. Biopharm. , 2008 , 68 , 667 .
6.
Hashimoto M.
,
Okamoto S.
,
Nabeta K.
, and
Hatanaka Y.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 2447 .
7.
Shen Z.X.
,
Zhang Y. W.
, and
Zhou C. G.
, Chin. J. Syn. Chem. , 2002 , 10 , 359 .
8.
Bhuniya S.
,
Park S. M.
, and
Kim B. H.
, Org. Lett. , 2005 , 7 , 1741 .
9.
Singh P.
,
Hurrell C. R.
,
Findlay J. B. C.
, and
Fishwick C. W. G.
, Bioorg. Med. Chem. Lett. , 1997 , 7 , 715 .
