Journal article

Publication year: 2016

Pages: 3215-3220

Journal: Organometallics

Volume number: 35

Issue number: 18

DOI Link: https://doi.org/10.1021/acs.organomet.6b00561

Publisher: American Chemical Society

Abstract: 

We report the first successful attachment of peptides to tin sulfide clusters. For proof of principle, H-l-Phe hydrazide and Boc-protected dipeptide hydrazides (Boc-l-Ala-l-Ala hydrazide and Boc-l-Val-l-Phe hydrazide) were reacted with keto-functionalized tin sulfide clusters [(R¹Sn)₄S₆] (A; R¹ = CMe₂CH₂C(O)Me) and [(R¹Sn)₃S₄Cl] (B). In the first case, we obtained single crystals of an amino acid functionalized Sn/S cluster, [R²₂Sn₄S₅] (1; R² = (CMe₂CH₂C(Me)N₂C(O)CH(CH₂Ph)NC(Me)CH₂CMe₂),
formed after inorganic cluster rearrangement and intramolecular
condensation of the amino acid ligand. By means of NMR spectroscopic
investigations and ESI/LIFDI mass spectrometry, we demonstrate that both
dipeptides are attached to B under retention of the original cluster architecture to yield [(R³Sn)₃S₄Cl] (2; R³ = CMe₂CH₂C(NNH-Ala-Ala-Boc)Me) and [(R⁴Sn)₃S₄Cl] (3; R⁴ = CMe₂CH₂C(NNH-Phe-Val-Boc)Me), as evident from mass spectrometric data of their cations [(R³Sn)₃S₄]⁺ (2⁺) and [(R⁴Sn)₃S₄]⁺ (3⁺).

Harvard Citation style: Rinn, N., Berndt, J., Kreher, A., Hrdina, R., Reinmuth, M., Schreiner, P., et al. (2016) Peptide-Functionalized Organotin Sulfide Clusters, Organometallics, 35(18), pp. 3215-3220. https://doi.org/10.1021/acs.organomet.6b00561

APA Citation style: Rinn, N., Berndt, J., Kreher, A., Hrdina, R., Reinmuth, M., Schreiner, P., & Dehnen, S. (2016). Peptide-Functionalized Organotin Sulfide Clusters. Organometallics. 35(18), 3215-3220. https://doi.org/10.1021/acs.organomet.6b00561