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Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach

A new strategy for the synthesis of peptide-boronic acids (PBAs) is presented. 20 Fmoc-protected natural amino acids with orthogonal side-chain protection were straightforwardly converted into their corresponding boron analogues in three simple steps. Subsequent immobilisation on commercially availa...

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Hauptverfasser: Hinkes, Stefan (VerfasserIn) , Kämmerer, Severin (VerfasserIn) , Klein, Christian D. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 21 Aug 2020
In: Chemical science
Year: 2020, Jahrgang: 11, Heft: 36, Pages: 9898-9903
ISSN:2041-6539
DOI:10.1039/D0SC03999C
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D0SC03999C
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc03999c
Volltext
Verfasserangaben:Stefan P.A. Hinkes, Severin Kämmerer, and Christian D.P. Klein
Beschreibung
Zusammenfassung:A new strategy for the synthesis of peptide-boronic acids (PBAs) is presented. 20 Fmoc-protected natural amino acids with orthogonal side-chain protection were straightforwardly converted into their corresponding boron analogues in three simple steps. Subsequent immobilisation on commercially available 1-glycerol polystyrene resin and on-resin transformations yielded a diversity of sequences in high purity. The strategy eliminates various synthetic obstacles such as multi-step routes, low yields, and inseparable impurities. The described method comprises great potential to be implemented in automated combinatorial approaches by markedly facilitating the access to a variety of PBAs. The coupling of amino acids or other building blocks with α-aminoboronates allows the creation of hybrid molecules with significant potential in various scientific disciplines, such as medicinal chemistry, structural biology, and materials science.
Beschreibung:Gesehen am 13.10.2020
Beschreibung:Online Resource
ISSN:2041-6539
DOI:10.1039/D0SC03999C

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