Biosynthesis of Vitroprocines by α-Oxoamine Synthase and Oxidoreductase Identified from Vibrio sp. QWI-06

Chih Chuang Liaw; Li Hua Lo; Tien Hsing Cheng; Yuen Ting Chan; Yu Ru Huang; Andrew H.J. Wang; Hsin Yang Chang

doi:10.1021/acs.orglett.2c01178

Biosynthesis of Vitroprocines by α-Oxoamine Synthase and Oxidoreductase Identified from Vibrio sp. QWI-06

Chih Chuang Liaw^*, Li Hua Lo, Tien Hsing Cheng, Yuen Ting Chan, Yu Ru Huang, Andrew H.J. Wang, Hsin Yang Chang^*

^*Corresponding author for this work

Department of Life Sciences and Institute of Genome Sciences

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

Abstract

A specific α-oxoamine synthase (VsAOS-2) and an oxidoreductase (VsOR) identified from marine Vibrio sp. QWI-06 were involved in the decarboxylative condensation of l-tyrosine to lauroyl-CoA following the reduction of the ketone group to form vitroprocine-type compound 1. The intermediates and products were characterized through HR-MS and their MS/MS fragmentations. This study reveals the biosynthetic pathway of vitroprocines and provides a useful model for elucidating the reaction mechanism underlying the production of amino acid-polyketide derivatives in microorganisms.

Original language	English
Pages (from-to)	3281-3285
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.2c01178
State	Published - 6 May 2022

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title = "Biosynthesis of Vitroprocines by α-Oxoamine Synthase and Oxidoreductase Identified from Vibrio sp. QWI-06",

abstract = "A specific α-oxoamine synthase (VsAOS-2) and an oxidoreductase (VsOR) identified from marine Vibrio sp. QWI-06 were involved in the decarboxylative condensation of l-tyrosine to lauroyl-CoA following the reduction of the ketone group to form vitroprocine-type compound 1. The intermediates and products were characterized through HR-MS and their MS/MS fragmentations. This study reveals the biosynthetic pathway of vitroprocines and provides a useful model for elucidating the reaction mechanism underlying the production of amino acid-polyketide derivatives in microorganisms.",

author = "Liaw, {Chih Chuang} and Lo, {Li Hua} and Cheng, {Tien Hsing} and Chan, {Yuen Ting} and Huang, {Yu Ru} and Wang, {Andrew H.J.} and Chang, {Hsin Yang}",

year = "2022",

month = may,

day = "6",

doi = "10.1021/acs.orglett.2c01178",

language = "English",

volume = "24",

pages = "3281--3285",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

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TY - JOUR

T1 - Biosynthesis of Vitroprocines by α-Oxoamine Synthase and Oxidoreductase Identified from Vibrio sp. QWI-06

AU - Liaw, Chih Chuang

AU - Lo, Li Hua

AU - Cheng, Tien Hsing

AU - Chan, Yuen Ting

AU - Huang, Yu Ru

AU - Wang, Andrew H.J.

AU - Chang, Hsin Yang

PY - 2022/5/6

Y1 - 2022/5/6

N2 - A specific α-oxoamine synthase (VsAOS-2) and an oxidoreductase (VsOR) identified from marine Vibrio sp. QWI-06 were involved in the decarboxylative condensation of l-tyrosine to lauroyl-CoA following the reduction of the ketone group to form vitroprocine-type compound 1. The intermediates and products were characterized through HR-MS and their MS/MS fragmentations. This study reveals the biosynthetic pathway of vitroprocines and provides a useful model for elucidating the reaction mechanism underlying the production of amino acid-polyketide derivatives in microorganisms.

AB - A specific α-oxoamine synthase (VsAOS-2) and an oxidoreductase (VsOR) identified from marine Vibrio sp. QWI-06 were involved in the decarboxylative condensation of l-tyrosine to lauroyl-CoA following the reduction of the ketone group to form vitroprocine-type compound 1. The intermediates and products were characterized through HR-MS and their MS/MS fragmentations. This study reveals the biosynthetic pathway of vitroprocines and provides a useful model for elucidating the reaction mechanism underlying the production of amino acid-polyketide derivatives in microorganisms.

UR - http://www.scopus.com/inward/record.url?scp=85129251529&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c01178

DO - 10.1021/acs.orglett.2c01178

M3 - Article

C2 - 35467888

AN - SCOPUS:85129251529

SN - 1523-7060

VL - 24

SP - 3281

EP - 3285

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Biosynthesis of Vitroprocines by α-Oxoamine Synthase and Oxidoreductase Identified from Vibrio sp. QWI-06

Abstract

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