Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37

Fleurdeliz Maglangit* (Corresponding Author), Ming Him Tong, Marcel Jaspars, Kwaku Kyeremeh, Hai Deng (Corresponding Author)

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report describing a siderophore containing the N-hydroxyl phenylacetyl cadaverine (HPAC) moiety in the structure. Based on bioinformatics analysis and previous knowledge of the biosynthesis of the hydroxamate-type siderophore, the biosynthetic gene cluster (lgo) responsible for the production of 1–3 was identified in the annotated genome of the producing strain. The supplementation of phenylacetate and benzoate analogues with meta substitution into the cultures of Streptomyces sp. MA37 resulted in the production of new legonoxamine A derivatives as observed in LC-HR-ESIMS, suggesting that the legonoxamine biosynthetic pathway has a good degree of natural flexibility of accepting unnatural precursors with different functional groups.

Original languageEnglish
Pages (from-to)75-79
Number of pages5
JournalTetrahedron Letters
Volume60
Issue number1
Early online date24 Nov 2018
DOIs
Publication statusPublished - 3 Jan 2019

Fingerprint

Siderophores
Streptomyces
Bacteria
Soil
Soils
Genes
Cadaverine
Deferoxamine
Benzoates
Biosynthesis
Biosynthetic Pathways
Bioinformatics
Multigene Family
Computational Biology
Hydroxyl Radical
Functional groups
Substitution reactions
Nuclear magnetic resonance
Genome
Derivatives

Keywords

  • Hydroxamates
  • Legonoxamine
  • Precursor-directed biosynthesis
  • Siderophores
  • Streptomyces sp. MA37
  • BIOSYNTHESIS
  • CHEMISTRY
  • IRON ACQUISITION
  • IDENTIFICATION
  • NEOCARAZOSTATIN

ASJC Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37. / Maglangit, Fleurdeliz (Corresponding Author); Tong, Ming Him; Jaspars, Marcel; Kyeremeh, Kwaku; Deng, Hai (Corresponding Author).

In: Tetrahedron Letters, Vol. 60, No. 1, 03.01.2019, p. 75-79.

Research output: Contribution to journalArticle

Maglangit, Fleurdeliz ; Tong, Ming Him ; Jaspars, Marcel ; Kyeremeh, Kwaku ; Deng, Hai. / Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37. In: Tetrahedron Letters. 2019 ; Vol. 60, No. 1. pp. 75-79.
@article{79003b5d2a434d3b96fd3a722d65c790,
title = "Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37",
abstract = "Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report describing a siderophore containing the N-hydroxyl phenylacetyl cadaverine (HPAC) moiety in the structure. Based on bioinformatics analysis and previous knowledge of the biosynthesis of the hydroxamate-type siderophore, the biosynthetic gene cluster (lgo) responsible for the production of 1–3 was identified in the annotated genome of the producing strain. The supplementation of phenylacetate and benzoate analogues with meta substitution into the cultures of Streptomyces sp. MA37 resulted in the production of new legonoxamine A derivatives as observed in LC-HR-ESIMS, suggesting that the legonoxamine biosynthetic pathway has a good degree of natural flexibility of accepting unnatural precursors with different functional groups.",
keywords = "Hydroxamates, Legonoxamine, Precursor-directed biosynthesis, Siderophores, Streptomyces sp. MA37, BIOSYNTHESIS, CHEMISTRY, IRON ACQUISITION, IDENTIFICATION, NEOCARAZOSTATIN",
author = "Fleurdeliz Maglangit and Tong, {Ming Him} and Marcel Jaspars and Kwaku Kyeremeh and Hai Deng",
note = "KK, HD and MJ are grateful for the financial support through Leverhulme Trust-Royal Society Africa award (AA090088). FM thanks the University of the Philippines for the Faculty, Reps and Staff Development Program (FRAS DP) PhD grant fellowship. MHT and HD thank Leverhulme Trust research project (RPG-2014-418).",
year = "2019",
month = "1",
day = "3",
doi = "10.1016/j.tetlet.2018.11.063",
language = "English",
volume = "60",
pages = "75--79",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "PERGAMON-ELSEVIER SCIENCE LTD",
number = "1",

}

TY - JOUR

T1 - Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37

AU - Maglangit, Fleurdeliz

AU - Tong, Ming Him

AU - Jaspars, Marcel

AU - Kyeremeh, Kwaku

AU - Deng, Hai

N1 - KK, HD and MJ are grateful for the financial support through Leverhulme Trust-Royal Society Africa award (AA090088). FM thanks the University of the Philippines for the Faculty, Reps and Staff Development Program (FRAS DP) PhD grant fellowship. MHT and HD thank Leverhulme Trust research project (RPG-2014-418).

PY - 2019/1/3

Y1 - 2019/1/3

N2 - Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report describing a siderophore containing the N-hydroxyl phenylacetyl cadaverine (HPAC) moiety in the structure. Based on bioinformatics analysis and previous knowledge of the biosynthesis of the hydroxamate-type siderophore, the biosynthetic gene cluster (lgo) responsible for the production of 1–3 was identified in the annotated genome of the producing strain. The supplementation of phenylacetate and benzoate analogues with meta substitution into the cultures of Streptomyces sp. MA37 resulted in the production of new legonoxamine A derivatives as observed in LC-HR-ESIMS, suggesting that the legonoxamine biosynthetic pathway has a good degree of natural flexibility of accepting unnatural precursors with different functional groups.

AB - Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report describing a siderophore containing the N-hydroxyl phenylacetyl cadaverine (HPAC) moiety in the structure. Based on bioinformatics analysis and previous knowledge of the biosynthesis of the hydroxamate-type siderophore, the biosynthetic gene cluster (lgo) responsible for the production of 1–3 was identified in the annotated genome of the producing strain. The supplementation of phenylacetate and benzoate analogues with meta substitution into the cultures of Streptomyces sp. MA37 resulted in the production of new legonoxamine A derivatives as observed in LC-HR-ESIMS, suggesting that the legonoxamine biosynthetic pathway has a good degree of natural flexibility of accepting unnatural precursors with different functional groups.

KW - Hydroxamates

KW - Legonoxamine

KW - Precursor-directed biosynthesis

KW - Siderophores

KW - Streptomyces sp. MA37

KW - BIOSYNTHESIS

KW - CHEMISTRY

KW - IRON ACQUISITION

KW - IDENTIFICATION

KW - NEOCARAZOSTATIN

UR - http://www.scopus.com/inward/record.url?scp=85057155636&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.11.063

DO - 10.1016/j.tetlet.2018.11.063

M3 - Article

VL - 60

SP - 75

EP - 79

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 1

ER -