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

Noé Osorio Reineke; Franziska A.V. Elsen; Hanusch A. Grab; Dietrich Mostert; Stephan A. Sieber; Thorsten Bach

doi:10.1039/d4cc02946a

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

Noé Osorio Reineke, Franziska A.V. Elsen, Hanusch A. Grab, Dietrich Mostert, Stephan A. Sieber, Thorsten Bach

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	8272-8275
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	63
DOIs	https://doi.org/10.1039/d4cc02946a
State	Published - 15 Jul 2024

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abstract = "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.",

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AU - Osorio Reineke, Noé

AU - Elsen, Franziska A.V.

AU - Grab, Hanusch A.

AU - Mostert, Dietrich

AU - Sieber, Stephan A.

AU - Bach, Thorsten

PY - 2024/7/15

Y1 - 2024/7/15

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85199080870

U2 - 10.1039/d4cc02946a

DO - 10.1039/d4cc02946a

M3 - Article

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AN - SCOPUS:85199080870

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VL - 60

SP - 8272

EP - 8275

JO - Chemical Communications

JF - Chemical Communications

IS - 63

ER -

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

Abstract

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