ISBN: 978-83-60043-10-3 - eurobic9

Eurobic9, 2-6 September, 2008, Wrocław, Poland
P94. ESI-MS Investigation of Interactions of Peptide-derived Amadori
Products with Borate
M. Kijewska, P. Stefanowicz, K. Kapczyńska, Z. Szewczuk
Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland,
e-mail: monikabr@eto.wchuwr.pl
Non-enzymatic glyaction products are complex and heterogeneous group of compounds which accumulate in
plasma and tissues and may play a role in the pathogenesis of diabetes, rethinopathy, cataracta, atherosclerosis,
nephropathy and neurological diseases such Alzheimer’s disease [1, 2].
We have obtained a series of glycated peptides derived from the fragments of bovine serum albumin using two
independent methods. First method involved reductive alkylation of the ε-amino groups of lysine with 2, 3:4, 5di-O-isopropylidene-β-arabino-hexos-2-ulo-2,
6-pyranose in the presence of sodium cyanoborohydride on a
solid support [3]. The secend approach is based on the synthesis of a suitable building block containing protected
fructose residue attached to the ε-amino group of lysine. The novel lysine derivative:
Fmoc-Lys(Fru, Boc)-OH is compatible with the Fmoc protocol of solid phase peptide synthesis [4].
According to literature data borate is well known for its ability to form complex with hydroxyl groups and has
been used as a complexing buffer in CE for the separation of sugars [5]. Moreover, CE is fast and convenient
method for separation of glycated peptides which is also benefits from complexation with borate [6].
In the present study we investigated the formation of borate complex of the peptide-derived Amadori products
by MS experiment. The fragmentation pathways of obtained complexes were also analyzed in order to find the
characteristic fragments ions.
References:
[1] A. Lapolla, P.Traldi, D. Fedele, Clin. Biochem., 38, 103 (2005).
[2] N. Ahmed, Diabetes Res. Clin. Pr., 67, 3 (2005).
[3] P. Stefanowicz, K. Kapczyńska, A. Kluczyk, Z. Szewczuk, Tetrahedron Lett., 48, 967 (2007).
[4] K. Kapczyńska, P. Stefanowicz, M. Brunatna, Z. Szewczuk, 19. Polskie Sympozjum Peptydowe, 23-27 IX
2007, Pułtusk, Polska
[5] S. Hoffstetter-Khun, A. Paulus, E. Gassmann, Anal. Chem., 63, 1541 (1991).
[6] L. Royle, R.G. Bailey, J.M. Ames, Food Chem. 62, 425 (1998).
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