Paper: Electron-induced damage of biotin studied in the gas phase and in the condensed phase at a single-molecule level

Adrian Keller1,2, Janina Kopyra3, Kurt V Gothelf2 and Ilko Bald2,4,5,6

New J. Phys. 2013 Aug, 15, no. 083045, doi: 10.1088/1367-2630/15/8/083045

Abstract

Biotin is an essential vitamin that is, on the one hand, relevant for the metabolism, gene expression and in the cellular response to DNA damage and, on the other hand, finds numerous applications in biotechnology. The functionality of biotin is due to two particular sub-structures, the ring structure and the side chain with carboxyl group. The heterocyclic ring structure results in the capability of biotin to form strong intermolecular hydrogen and van der Waals bonds with proteins such as streptavidin, whereas the carboxyl group can be employed to covalently bind biotin to other complex molecules. Dissociative electron attachment (DEA) to biotin results in a decomposition of the ring structure and the carboxyl group, respectively, within resonant features in the energy range 0–12 eV, thereby preventing the capability of biotin for intermolecular binding and covalent coupling to other molecules. Specifically, the fragment anions (M–H), (M–O), C3N2O, CH2O2, OCN, CN, OH and O are observed, and exemplarily the DEA cross section of OCN formation is determined to be 3 × 10−19 cm2. To study the response of biotin to electrons within a complex condensed environment, we use the DNA origami technique and determine a dissociation yield of (1.1 ± 0.2) × 10−14 cm2 at 18 eV electron energy, which represents the most relevant energy for biomolecular damage induced by secondary electrons. The present results thus have important implications for the use of biotin as a label in radiation experiments.

Author Information

1 Institute of Ion Beam Physics and Materials Research, Helmholtz-Zentrum Dresden-Rossendorf, Bautzner Landstrasse 400, D-01328 Dresden, Germany
2 Interdisciplinary Nanoscience Center (iNANO) and Danish National Research Foundation: Centre for DNA Nanotechnology (CDNA), Aarhus University, DK-8000 Aarhus C, Denmark
3 Chemistry Department, Siedlce University, 3 Maja 54, 08-110 Siedlce, Poland
4 Department of Chemistry—Physical Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany
5 BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany
6 Author to whom any correspondence should be addressed.

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