Genome Mining Reveals a Carboxyl O-Methyltransferase Gatekeeping the Biosynthetic Divergence of Tryptophan Dimers

Liang Ma; Zhiwen Liu; Wenjun Zhang; Yiguang Zhu; Liping Zhang; Weiliang Xiong; Xiao Nian Li; Xinpeng Tian; Changsheng Zhang

doi:10.1021/acs.orglett.5c01012

Genome Mining Reveals a Carboxyl O-Methyltransferase Gatekeeping the Biosynthetic Divergence of Tryptophan Dimers

Liang Ma
, Zhiwen Liu
, Wenjun Zhang
, Yiguang Zhu
, Liping Zhang
, Weiliang Xiong
, Xiao Nian Li
, Xinpeng Tian
, Changsheng Zhang

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Bacterial tryptophan dimers comprise a large family of natural products with promising biological activities. Herein, we report the identification of a methyltransferase, SpmM1, which acts as a gatekeeping enzyme to govern the divergent biosynthesis of tryptophan dimers spiroindimicins (SPMs) and indimicins (IDMs) in Streptomyces marincola SCSIO 03032. Bioinformatics, genetic, and biochemical studies revealed that SpmM1-catalyzed carboxyl O-methylation enabled the common precursor of SPMs and IDMs to flux into the spiro-forming pathway to generate SPMs.

Original language	English (US)
Pages (from-to)	5936-5941
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.5c01012
State	Published - Jun 13 2025
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c01012

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title = "Genome Mining Reveals a Carboxyl O-Methyltransferase Gatekeeping the Biosynthetic Divergence of Tryptophan Dimers",

abstract = "Bacterial tryptophan dimers comprise a large family of natural products with promising biological activities. Herein, we report the identification of a methyltransferase, SpmM1, which acts as a gatekeeping enzyme to govern the divergent biosynthesis of tryptophan dimers spiroindimicins (SPMs) and indimicins (IDMs) in Streptomyces marincola SCSIO 03032. Bioinformatics, genetic, and biochemical studies revealed that SpmM1-catalyzed carboxyl O-methylation enabled the common precursor of SPMs and IDMs to flux into the spiro-forming pathway to generate SPMs.",

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language = "English (US)",

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T1 - Genome Mining Reveals a Carboxyl O-Methyltransferase Gatekeeping the Biosynthetic Divergence of Tryptophan Dimers

AU - Ma, Liang

AU - Liu, Zhiwen

AU - Zhang, Wenjun

AU - Zhu, Yiguang

AU - Zhang, Liping

AU - Xiong, Weiliang

AU - Li, Xiao Nian

AU - Tian, Xinpeng

AU - Zhang, Changsheng

PY - 2025/6/13

Y1 - 2025/6/13

N2 - Bacterial tryptophan dimers comprise a large family of natural products with promising biological activities. Herein, we report the identification of a methyltransferase, SpmM1, which acts as a gatekeeping enzyme to govern the divergent biosynthesis of tryptophan dimers spiroindimicins (SPMs) and indimicins (IDMs) in Streptomyces marincola SCSIO 03032. Bioinformatics, genetic, and biochemical studies revealed that SpmM1-catalyzed carboxyl O-methylation enabled the common precursor of SPMs and IDMs to flux into the spiro-forming pathway to generate SPMs.

AB - Bacterial tryptophan dimers comprise a large family of natural products with promising biological activities. Herein, we report the identification of a methyltransferase, SpmM1, which acts as a gatekeeping enzyme to govern the divergent biosynthesis of tryptophan dimers spiroindimicins (SPMs) and indimicins (IDMs) in Streptomyces marincola SCSIO 03032. Bioinformatics, genetic, and biochemical studies revealed that SpmM1-catalyzed carboxyl O-methylation enabled the common precursor of SPMs and IDMs to flux into the spiro-forming pathway to generate SPMs.

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JO - Organic Letters

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Genome Mining Reveals a Carboxyl O-Methyltransferase Gatekeeping the Biosynthetic Divergence of Tryptophan Dimers

Abstract

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