Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37

Michiel T. Uiterweerd; Isabel Nunez Santiago; Helga van der Heul; Gilles P. van Wezel; Adriaan J. Minnaard

doi:10.1002/ejoc.202000767

Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37

Michiel T. Uiterweerd, Isabel Nunez Santiago, Helga van der Heul, Gilles P. van Wezel, Adriaan J. Minnaard^*

^*Corresponding author for this work

Chemical Biology 2

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

2 Citations (Scopus)

175 Downloads (Pure)

Abstract

Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 µg/mL.

Original language	English
Pages (from-to)	5145-5152
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.202000767
Publication status	Published - 31-Aug-2020

Keywords

Maleimycin
Streptomyces sp
Actinomycetes
Antibiotics
GC-MS
NATURAL-PRODUCTS
BIOSYNTHESIS
SHOWDOMYCIN
NITROSPOREUSINES
ANTIBIOTICS
ALKALOIDS

Access to Document

10.1002/ejoc.202000767Licence: CC BY

Iso‐maleimycin, a Constitutional Isomer of Maleimycin, from Streptomyces sp. QL37Final publisher's version, 1.24 MBLicence: CC BY

Handle.net

Persistent link

Cite this

@article{6f4b5a7d1aab48d5b9506c176ebd3f52,

title = "Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37",

abstract = "Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 µg/mL.",

keywords = "Maleimycin, Streptomyces sp, Actinomycetes, Antibiotics, GC-MS, NATURAL-PRODUCTS, BIOSYNTHESIS, SHOWDOMYCIN, NITROSPOREUSINES, ANTIBIOTICS, ALKALOIDS",

author = "Uiterweerd, {Michiel T.} and Santiago, {Isabel Nunez} and {van der Heul}, Helga and {van Wezel}, {Gilles P.} and Minnaard, {Adriaan J.}",

year = "2020",

month = aug,

day = "31",

doi = "10.1002/ejoc.202000767",

language = "English",

volume = "2020",

pages = "5145--5152",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "32",

}

TY - JOUR

T1 - Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37

AU - Uiterweerd, Michiel T.

AU - Santiago, Isabel Nunez

AU - van der Heul, Helga

AU - van Wezel, Gilles P.

AU - Minnaard, Adriaan J.

PY - 2020/8/31

Y1 - 2020/8/31

N2 - Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 µg/mL.

AB - Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 µg/mL.

KW - Maleimycin

KW - Streptomyces sp

KW - Actinomycetes

KW - Antibiotics

KW - GC-MS

KW - NATURAL-PRODUCTS

KW - BIOSYNTHESIS

KW - SHOWDOMYCIN

KW - NITROSPOREUSINES

KW - ANTIBIOTICS

KW - ALKALOIDS

U2 - 10.1002/ejoc.202000767

DO - 10.1002/ejoc.202000767

M3 - Article

SN - 1434-193X

VL - 2020

SP - 5145

EP - 5152

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this