Synthesis and biological evaluation of vioprolide B and its dehydrobutyrine-glycine analogue

被引：0
|
作者：
Reineke, Noe Osorio [1 ,2 ]
Elsen, Franziska A. V. [3 ,4 ]
Grab, Hanusch A. [1 ,2 ]
Mostert, Dietrich [3 ,4 ]
Sieber, Stephan A. [3 ,4 ]
Bach, Thorsten [1 ,2 ]
机构：
[1] Tech Univ Munich, Sch Nat Sci, Dept Chem, Lichtenbergstr 4, D-85747 Garching, Germany
[2] Catalysis Res Ctr, Lichtenbergstr 4, D-85747 Garching, Germany
[3] Tech Univ Munich, Sch Nat Sci, Dept Biosci, Ernst Otto Fischer Str 8, D-85747 Garching, Germany
[4] Ctr Funct Prot Assemblies, Ernst Otto Fischer Str 8, D-85747 Garching, Germany
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 63期
关键词：
ELECTROPHILIC NATURAL-PRODUCTS; AMIDE BOND FORMATION; ACID; ESTERS; 1-HYDROXY-7-AZABENZOTRIAZOLE; ANTIBIOTICS; THIAZOLINES; DISCOVERY; PEPTIDES; FRAGMENT;
D O I：
10.1039/d4cc02946a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we describe the total synthesis of the depsipeptide vioprolide B and of an analogue, in which the (E)-dehydrobutyrine amino acid was replaced by glycine. The compounds were studied in biological assays which revealed cytotoxicity solely for vioprolide B presumably by covalent binding to cysteine residues of elongation factor eEF1A1 and of chromatin assembly factor CHAF1A. Vioprolide B and an analogue, in which the (E)-dehydrobutyrine was replaced by glycine, were synthesized and studied in biological assays which revealed cytotoxicity solely for vioprolide B, presumably by covalent binding to the target protein.
引用
收藏
页码：8272 / 8275
页数：4
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