Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti

Rolf Jansen; Klaus Gerth; Heinrich Steinmetz; Silke Reinecke; Wolfgang Kessler; Andreas Kirschning; Rolf Müller

doi:10.1002/chem.201100457

Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti

Rolf Jansen^*
, Klaus Gerth
, Heinrich Steinmetz
, Silke Reinecke
, Wolfgang Kessler
, Andreas Kirschning
, Rolf Müller

^*Corresponding author for this work

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

Abstract

Hen or egg? The polyketide-based p-quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1-A3 was observed. Under mild acidic conditions a Grob-type fragmentation of elansolid A3 led to the p-hydroxy styryl isomer elansolid D.

Original language	English
Pages (from-to)	7739-7744
Number of pages	6
Journal	Chemistry - A European Journal
Volume	17
Issue number	28
DOIs	https://doi.org/10.1002/chem.201100457
Publication status	Published - 30 May 2011

Keywords

antibiotics
Chitinophaga sancti
Grob fragmentation
molecular modeling
quinone methide

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201100457

Cite this

@article{03de44aae0e944dd9dd7f1932008a409,

title = "Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti",

abstract = "Hen or egg? The polyketide-based p-quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1-A3 was observed. Under mild acidic conditions a Grob-type fragmentation of elansolid A3 led to the p-hydroxy styryl isomer elansolid D.",

keywords = "antibiotics, Chitinophaga sancti, Grob fragmentation, molecular modeling, quinone methide",

author = "Rolf Jansen and Klaus Gerth and Heinrich Steinmetz and Silke Reinecke and Wolfgang Kessler and Andreas Kirschning and Rolf M{\"u}ller",

year = "2011",

month = may,

day = "30",

doi = "10.1002/chem.201100457",

language = "English",

volume = "17",

pages = "7739--7744",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "28",

}

TY - JOUR

T1 - Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti

AU - Jansen, Rolf

AU - Gerth, Klaus

AU - Steinmetz, Heinrich

AU - Reinecke, Silke

AU - Kessler, Wolfgang

AU - Kirschning, Andreas

AU - Müller, Rolf

PY - 2011/5/30

Y1 - 2011/5/30

N2 - Hen or egg? The polyketide-based p-quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1-A3 was observed. Under mild acidic conditions a Grob-type fragmentation of elansolid A3 led to the p-hydroxy styryl isomer elansolid D.

AB - Hen or egg? The polyketide-based p-quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1-A3 was observed. Under mild acidic conditions a Grob-type fragmentation of elansolid A3 led to the p-hydroxy styryl isomer elansolid D.

KW - antibiotics

KW - Chitinophaga sancti

KW - Grob fragmentation

KW - molecular modeling

KW - quinone methide

UR - https://www.scopus.com/pages/publications/79959661944

U2 - 10.1002/chem.201100457

DO - 10.1002/chem.201100457

M3 - Article

C2 - 21626585

AN - SCOPUS:79959661944

SN - 0947-6539

VL - 17

SP - 7739

EP - 7744

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 28

ER -

Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this