Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

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 Streptomyces spectabilis confirmed its S config...

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Autores principales: Xu, Houchao, Wochele, Anne, Luo, Minghe, Schnakenburg, Gregor, Sun, Yuhui, Brötz-Oesterhelt, Heike, Dickschat, Jeroen S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9475180/
https://www.ncbi.nlm.nih.gov/pubmed/36128431
http://dx.doi.org/10.3762/bjoc.18.120
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author Xu, Houchao
Wochele, Anne
Luo, Minghe
Schnakenburg, Gregor
Sun, Yuhui
Brötz-Oesterhelt, Heike
Dickschat, Jeroen S
author_facet Xu, Houchao
Wochele, Anne
Luo, Minghe
Schnakenburg, Gregor
Sun, Yuhui
Brötz-Oesterhelt, Heike
Dickschat, Jeroen S
author_sort Xu, Houchao
collection PubMed
description 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 Streptomyces spectabilis confirmed its S 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(222) are given.
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spelling pubmed-94751802022-09-19 Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites Xu, Houchao Wochele, Anne Luo, Minghe Schnakenburg, Gregor Sun, Yuhui Brötz-Oesterhelt, Heike Dickschat, Jeroen S Beilstein J Org Chem Letter 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 Streptomyces spectabilis confirmed its S 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(222) are given. Beilstein-Institut 2022-09-07 /pmc/articles/PMC9475180/ /pubmed/36128431 http://dx.doi.org/10.3762/bjoc.18.120 Text en Copyright © 2022, Xu et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Xu, Houchao
Wochele, Anne
Luo, Minghe
Schnakenburg, Gregor
Sun, Yuhui
Brötz-Oesterhelt, Heike
Dickschat, Jeroen S
Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title_full Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title_fullStr Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title_full_unstemmed Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title_short Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
title_sort synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9475180/
https://www.ncbi.nlm.nih.gov/pubmed/36128431
http://dx.doi.org/10.3762/bjoc.18.120
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