Cargando…

Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity

A new cyclic lipopeptide, phototemtide A (1), was isolated from Escherichia coli expressing the biosynthetic gene cluster pttABC from Photorhabdus temperata Meg1. The structure of 1 was elucidated by HR‐ESI‐MS and NMR experiments. The absolute configurations of amino acids and 3‐hydroxyoctanoic acid...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhao, Lei, Vo, Tien Duy, Kaiser, Marcel, Bode, Helge B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317862/
https://www.ncbi.nlm.nih.gov/pubmed/31814269
http://dx.doi.org/10.1002/cbic.201900665
_version_ 1783550724267835392
author Zhao, Lei
Vo, Tien Duy
Kaiser, Marcel
Bode, Helge B.
author_facet Zhao, Lei
Vo, Tien Duy
Kaiser, Marcel
Bode, Helge B.
author_sort Zhao, Lei
collection PubMed
description A new cyclic lipopeptide, phototemtide A (1), was isolated from Escherichia coli expressing the biosynthetic gene cluster pttABC from Photorhabdus temperata Meg1. The structure of 1 was elucidated by HR‐ESI‐MS and NMR experiments. The absolute configurations of amino acids and 3‐hydroxyoctanoic acid in 1 were determined by using the advanced Marfey's method and comparison after total synthesis of 1, respectively. Additionally, three new minor derivatives, phototemtides B–D (2–4), were identified by detailed HPLC–MS analysis. Phototemtide A (1) showed weak antiprotozoal activity against Plasmodium falciparum, with an IC(50) value of 9.8 μm. The biosynthesis of phototemtides A–D (1–4) was also proposed.
format Online
Article
Text
id pubmed-7317862
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-73178622020-06-29 Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity Zhao, Lei Vo, Tien Duy Kaiser, Marcel Bode, Helge B. Chembiochem Communications A new cyclic lipopeptide, phototemtide A (1), was isolated from Escherichia coli expressing the biosynthetic gene cluster pttABC from Photorhabdus temperata Meg1. The structure of 1 was elucidated by HR‐ESI‐MS and NMR experiments. The absolute configurations of amino acids and 3‐hydroxyoctanoic acid in 1 were determined by using the advanced Marfey's method and comparison after total synthesis of 1, respectively. Additionally, three new minor derivatives, phototemtides B–D (2–4), were identified by detailed HPLC–MS analysis. Phototemtide A (1) showed weak antiprotozoal activity against Plasmodium falciparum, with an IC(50) value of 9.8 μm. The biosynthesis of phototemtides A–D (1–4) was also proposed. John Wiley and Sons Inc. 2020-02-04 2020-05-04 /pmc/articles/PMC7317862/ /pubmed/31814269 http://dx.doi.org/10.1002/cbic.201900665 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Zhao, Lei
Vo, Tien Duy
Kaiser, Marcel
Bode, Helge B.
Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title_full Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title_fullStr Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title_full_unstemmed Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title_short Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity
title_sort phototemtide a, a cyclic lipopeptide heterologously expressed from photorhabdus temperata meg1, shows selective antiprotozoal activity
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317862/
https://www.ncbi.nlm.nih.gov/pubmed/31814269
http://dx.doi.org/10.1002/cbic.201900665
work_keys_str_mv AT zhaolei phototemtideaacycliclipopeptideheterologouslyexpressedfromphotorhabdustemperatameg1showsselectiveantiprotozoalactivity
AT votienduy phototemtideaacycliclipopeptideheterologouslyexpressedfromphotorhabdustemperatameg1showsselectiveantiprotozoalactivity
AT kaisermarcel phototemtideaacycliclipopeptideheterologouslyexpressedfromphotorhabdustemperatameg1showsselectiveantiprotozoalactivity
AT bodehelgeb phototemtideaacycliclipopeptideheterologouslyexpressedfromphotorhabdustemperatameg1showsselectiveantiprotozoalactivity