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Direct carborane-peptide conjugates: Synthesis and evaluation as non-natural lipopeptide mimetics
Tamara Lützenburg1, Ines Neundorf1, Matthias Scholz2
1University of Cologne, Department of Chemistry, Biochemistry, Zülpicher Str. 47a, D-50674 Cologne, Germany.
Abstract:
Herein, we report the synthesis and characterization of direct carborane-peptide conjugates. Carboranes are non-natural and extremely hydrophobic compounds and turned out to be suitable pharmacophores for diverse biological applications. In this work, we established an efficient procedure for the coupling of carboranes to peptides on solid support. We identified the coupling of carborane-1-carboxylic acids to amino groups to be superior to those with hydroxy- or sulfhydryl-groups. The carborane-peptide conjugates showed remarkably prolonged, and carborane isomer dependent chromatographic retention times. This effect can be used to generate non-natural lipopeptides with fine-tuned properties.
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