Synthesis of Asp-based lactam cyclic peptides using an amide-bonded diaminodiacid to prevent aspartimide formation
Asp-based lactam cyclic peptides are considered promising drug candidates. However, using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) for these peptides also causes aspartimide formation, resulting in low yields or even failure to obtain the target peptides. Here, we developed a diaminodiacid containing an amide bond as a β-carboxyl-protecting group for Asp to avoid aspartimide formation. The practicality of this diaminodiacid has been illustrated by the synthesis of lactam cyclic peptide cyclo[Lys9,Asp13] KIIIA7-14 and 1Y.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2024 |
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| Enthalten in: |
Organic & biomolecular chemistry - (2024) vom: 16. Apr. |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Wen-Jie [VerfasserIn] |
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| Anmerkungen: |
Date Revised 16.04.2024 published: Print-Electronic Citation Status Publisher |
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| doi: |
10.1039/d4ob00472h |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM371129826 |
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| 245 | 1 | 0 | |a Synthesis of Asp-based lactam cyclic peptides using an amide-bonded diaminodiacid to prevent aspartimide formation |
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| 520 | |a Asp-based lactam cyclic peptides are considered promising drug candidates. However, using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) for these peptides also causes aspartimide formation, resulting in low yields or even failure to obtain the target peptides. Here, we developed a diaminodiacid containing an amide bond as a β-carboxyl-protecting group for Asp to avoid aspartimide formation. The practicality of this diaminodiacid has been illustrated by the synthesis of lactam cyclic peptide cyclo[Lys9,Asp13] KIIIA7-14 and 1Y | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Chen, Jun-You |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Hui-Xia |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Yi-Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Yang |e verfasserin |4 aut | |
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