色氨酸-脱氢丁氨酸二酮哌嗪的合成以及杭台霉素及其共代谢产物的生物活性
Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites.
作者信息
Xu Houchao, Wochele Anne, Luo Minghe, Schnakenburg Gregor, Sun Yuhui, Brötz-Oesterhelt Heike, Dickschat Jeroen S
机构信息
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
Interfaculty Institute of Microbiology and Infection Medicine, Department of Microbial Bioactive Compounds, University of Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany.
出版信息
Beilstein J Org Chem. 2022 Sep 7;18:1159-1165. doi: 10.3762/bjoc.18.120. eCollection 2022.
An improved synthesis for tryptophan-dehydrobutyrine diketopiperazine (TDD), a co-metabolite of the hybrid polyketide/non-ribosomal peptide hangtaimycin, starting from ʟ-tryptophan is presented. Comparison to TDD isolated from the hangtaimycin producer confirmed its configuration. The X-ray structure of the racemate shows an interesting dimerisation through hydrogen bridges. The results from bioactivity testings of hangtaimycin, TDD and the hangtaimycin degradation product HTM are given.
本文介绍了一种改进的从L-色氨酸出发合成色氨酸-脱氢丁氨酸二酮哌嗪（TDD）的方法，TDD是杂合聚酮/非核糖体肽汉他霉素的一种共代谢产物。将其与从汉他霉素产生菌中分离得到的TDD进行比较，确定了其构型。外消旋体的X射线结构显示通过氢键形成了有趣的二聚体。给出了汉他霉素、TDD和汉他霉素降解产物HTM的生物活性测试结果。
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