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

页码：8272 / 8275

页数：4

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