Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides

Thomas P. Wyche; Antonio C. Ruzzini; Christine Beemelmanns; Ki Hyun Kim; Jonathan L. Klassen; Shugeng Cao; Michael Thomas-Poulsen; Tim S. Bugni; Cameron R. Currie; Jon Clardy

doi:10.1021/acs.orglett.7b00545

Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides

Thomas P. Wyche
, Antonio C. Ruzzini
, Christine Beemelmanns
, Ki Hyun Kim
, Jonathan L. Klassen
, Shugeng Cao
, Michael Thomas-Poulsen
, Tim S. Bugni
, Cameron R. Currie
, Jon Clardy^*

^*Corresponding author af dette arbejde

Publikation: Bidrag til tidsskrift › Letter › peer review

Abstract

Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	19
Udgave nummer	7
Sider (fra-til)	1772-1775
Antal sider	4
ISSN	1523-7060
DOI	https://doi.org/10.1021/acs.orglett.7b00545
Status	Udgivet - 2017
Udgivet eksternt	Ja

Finansiering

We are grateful for financial support through the NIH (R01-GM086258 to J.C., RC4-GM096347 to J.C. and C.R.C., and R01-GM104192 to T.S.B.) and through the German National Academy of Sciences Leopoldina for a postdoctoral fellowship to C.B. (LPDS 2011-2). This research was also supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science ICT, and Future Planning (2015R1C1A1A02037383). A.C.R. was supported by a PDF from the Canadian Institutes of Health Research.

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Citationsformater

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title = "Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides",

abstract = "Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.",

author = "Wyche, \{Thomas P.\} and Ruzzini, \{Antonio C.\} and Christine Beemelmanns and Kim, \{Ki Hyun\} and Klassen, \{Jonathan L.\} and Shugeng Cao and Michael Thomas-Poulsen and Bugni, \{Tim S.\} and Currie, \{Cameron R.\} and Jon Clardy",

year = "2017",

doi = "10.1021/acs.orglett.7b00545",

language = "English",

volume = "19",

pages = "1772--1775",

journal = "Organic Letters",

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TY - JOUR

T1 - Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides

AU - Wyche, Thomas P.

AU - Ruzzini, Antonio C.

AU - Beemelmanns, Christine

AU - Kim, Ki Hyun

AU - Klassen, Jonathan L.

AU - Cao, Shugeng

AU - Thomas-Poulsen, Michael

AU - Bugni, Tim S.

AU - Currie, Cameron R.

AU - Clardy, Jon

PY - 2017

Y1 - 2017

N2 - Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.

AB - Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.

U2 - 10.1021/acs.orglett.7b00545

DO - 10.1021/acs.orglett.7b00545

M3 - Letter

C2 - 28326787

AN - SCOPUS:85017179138

SN - 1523-7060

VL - 19

SP - 1772

EP - 1775

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -