Journal
CHEMISTRY AND PHYSICS OF LIPIDS
Volume 213, Issue -, Pages 62-67Publisher
ELSEVIER IRELAND LTD
DOI: 10.1016/j.chemphyslip.2018.03.009
Keywords
Carborane; Boron; Cluster; Solid-phase peptide synthesis; Lipopeptides; Amphipathic peptides
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Funding
- Jiirgen-Manchot Stiftung
- German Research Foundation DFG [SCHO 1593/1-1]
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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-l-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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