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

Houchao Xu, Anne Wochele, Minghe Luo, Gregor Schnakenburg, Yuhui Sun, Heike Brötz-Oesterhelt and Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165. https://doi.org/10.3762/bjoc.18.120

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

Houchao Xu, Anne Wochele, Minghe Luo, Gregor Schnakenburg, Yuhui Sun, Heike Brötz-Oesterhelt and Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165. https://doi.org/10.3762/bjoc.18.120

How to Cite

Xu, H.; Wochele, A.; Luo, M.; Schnakenburg, G.; Sun, Y.; Brötz-Oesterhelt, H.; Dickschat, J. S. Beilstein J. Org. Chem. 2022, 18, 1159–1165. doi:10.3762/bjoc.18.120

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TY  - JOUR
A1  - Xu, Houchao
A1  - Wochele, Anne
A1  - Luo, Minghe
A1  - Schnakenburg, Gregor
A1  - Sun, Yuhui
A1  - Brötz-Oesterhelt, Heike
A1  - Dickschat, Jeroen S.
T1  - Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 1159
EP  - 1165
SN  - 1860-5397
DO  - 10.3762/bjoc.18.120
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.120
KW  - antibiotics
KW  - enantioselective synthesis
KW  - peptides
KW  - racemisation
KW  - Streptomyces
N2  - 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 HTM222 are given.
ER  -

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Scholarly Works

Luo, M.; Dong, Y.; Deng, Z.; Sun, Y. Methylation in hangtaimycin biosynthesis and its antibacterial activities. Synthetic and systems biotechnology 2023, 8, 682–687. doi:10.1016/j.synbio.2023.10.003
Koshizuka, M.; Shinoda, K.; Makino, K.; Shimada, N. Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations. The Journal of organic chemistry 2023, 88, 6901–6910. doi:10.1021/acs.joc.3c00195

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