Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/163433
Title: Enaminone formation drives the coupling of biosynthetic pathways to generate cyclic lipopeptides
Authors: Candra, Hartono
Ma, Guang-Lei
Lee, Sean Qiu En
Liang, Zhao-Xun
Keywords: Science::Biological sciences
Issue Date: 2022
Source: Candra, H., Ma, G., Lee, S. Q. E. & Liang, Z. (2022). Enaminone formation drives the coupling of biosynthetic pathways to generate cyclic lipopeptides. ChemBioChem, 23(22), e202200457-. https://dx.doi.org/doi.org/10.1002/cbic.202200457
Project: T2EP30221-0029
NRF-SBP-01 
Journal: ChemBioChem
Abstract: A family of novel cyclic lipopeptides named tasikamides A􀀀 H (Tsk A􀀀 H) were discovered recently in Streptomyces tasikensis P46. Aside from the unique cyclic pentapeptide scaffold shared by the tasikamides, Tsk A􀀀 C contain a hydrazone bridge that connects the cyclic pentapeptide to the lipophilic alkyl 5- hydroxylanthranilate (AHA) moiety. Here we report the production of tasikamides I􀀀 K (Tsk I􀀀 K) by a mutant strain of S. tasikensis P46 that overexpresses two pathway-specific transcription regulators. Unlike Tsk A􀀀 C, Tsk I􀀀 K feature a rare enaminone-bridge that links the cyclic peptide scaffold to the AHA moiety. Our experimental data suggest that Tsk I􀀀 K are generated by the coupling of two biosynthetic pathways via a nonenzymatic condensation reaction between an arylamine and a β-keto aldehyde-containing precursor. The results underscore the nucleophilic and electrophilic reactivity of the β-keto aldehyde moiety and its ability to
URI: https://hdl.handle.net/10356/163433
ISSN: 1439-7633
DOI: 10.1002/cbic.202200457
Schools: School of Biological Sciences 
Rights: © 2022 Wiley-VCH GmbH, Weinheim. All right reserved. This is the peer reviewed version of the following article: Candra, H., Ma, G., Lee, S. Q. E. & Liang, Z. (2022). Enaminone formation drives the coupling of biosynthetic pathways to generate cyclic lipopeptides. ChemBioChem, 23(22), e202200457-, which has been published in final form at https://doi.org/10.1002/cbic.202200457. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SBS Journal Articles

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