Book of Abstracts - Ruhr-Universität Bochum

P-39
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Metallocarbonyl Complexes of Bromo- and Dibromomaleimide. Synthesis and
Reactions with Cysteine Derivatives
Bogna Rudolf, a* Marcin Palusiak, b and Emilia Fornal c
a Department of Organic Chemistry, University of Łódź, Tamka 12, Łódź 91-403, Poland,
b Department of Crystalography and Crystal Chemistry, University of Lodz, Tamka 12,
Łódź 91-403, Poland
c Chemistry Department, Faculty of Mathematics and Life Sciencies, The John Paul II Catholic
University of Lublin, al. Krasnicka 102, 20-718 Lublin, E-mail:brudolf@chemia.uni.lodz.pl
The maleimide motif is widely used for the selective reactions with thiols and there are numerous N–
functionalized maleimide reagents applied for cysteine modification. Among them the (η 5 -
C5H5)M(CO)x(η 1 -N-maleimidato) (M = Fe, x = 2; M = W, Mo, x = 3) markers were reacted
with cysteine containing peptides and proteins. These metallocarbonyl complexes display
characteristic strong absorption bands in their IR spectra, �C≡O, appearing in the 1950-2060
cm -1 spectral region, which is usually free of any absorption of biomolecules or biological
matrices. 1,2
Recently it was reported that the bromomaleimide and its derivatives are of interest for
bioconjugation and reversible cysteine modification. 3,4
Fe
OC
OC
cysteine derivatives
In this communication, synthesis of metallocarbonyl derivatives of bromo- and dibromomaleimide
(e.g. 1) along with reactions of these complexes with cysteine derivatives will be presented.
References
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1. B. Rudolf, J. Zakrzewski, Tetrahedron Lett. 1994, 35, 9611-9612.
2. B. Rudolf, M. Palusiak, J. Zakrzewski, M. Salmain, G. Jaouen, Bioconjugate Chem. 2005, 16, 1218-
1224.
3. L. M. Tedaldi, M. E. B. Smith, R. I. Nathani, J. R Baker, Chem. Com. 2009, 43, 6583-6585.
4. M. E. B. Smith, F. F. Schumacher, C. P. Ryan, L. M. Tedaldi, D. Papaioannou, G. Waksman,
S. Caddick, J. R. Baker J. Am. Chem. Soc. 2010, 132, 1960-1965.
97
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Fe
O
N
O
S