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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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
21 Aug 2020
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| In: |
Chemical science
Year: 2020, Volume: 11, Issue: 36, Pages: 9898-9903 |
| ISSN: | 2041-6539 |
| DOI: | 10.1039/D0SC03999C |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D0SC03999C Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc03999c 
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| Author Notes: | Stefan P.A. Hinkes, Severin Kämmerer, and Christian D.P. Klein |
| Summary: | 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. |
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| Item Description: | Gesehen am 13.10.2020 |
| Physical Description: | Online Resource |
| ISSN: | 2041-6539 |
| DOI: | 10.1039/D0SC03999C |