Cryptand-imidazolium supported total synthesis of the lasso peptide BI-32169 and its d -enantiomer - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemical Communications Année : 2019

Cryptand-imidazolium supported total synthesis of the lasso peptide BI-32169 and its d -enantiomer

Résumé

Lasso peptides are attracting increasing attention due to their broad range of biological activities. The knot topology of lasso peptides, which contains an isopeptide bond-bridged macrocycle threaded by its C-terminal tail, has been proven to be an important structural feature for their bioactivities. The preparation of lasso peptides has been achieved by biosynthetic methods; nevertheless, a chemical synthesis of lasso peptides has not been described so far. Herein, a cryptand-imidazolium complex is designed as a multi-linker support and applied in the chemical synthesis of the lasso peptide BI-32169. Furthermore, the chiral switching of the support and the introduction of d-amino acids enable the synthesis of the d-enantiomer of BI-32169, which shows not only a strong glucagon receptor antagonist activity, but also a much higher enzymatic stability compared to the l-lasso peptide
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Dates et versions

hal-02094778 , version 1 (09-04-2019)

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Ming Chen, Shuanglong Wang, Xihan Yu. Cryptand-imidazolium supported total synthesis of the lasso peptide BI-32169 and its d -enantiomer. Chemical Communications, 2019, 55 (23), pp.3323-3326. ⟨10.1039/c8cc10301a⟩. ⟨hal-02094778⟩
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