Details
| Original language | English |
|---|---|
| Pages (from-to) | 7739-7744 |
| Number of pages | 6 |
| Journal | Chemistry - A European Journal |
| Volume | 17 |
| Issue number | 28 |
| Publication status | Published - 30 May 2011 |
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
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 17, No. 28, 30.05.2011, p. 7739-7744.
Research output: Contribution to journal › Article › Research › peer review
}
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 - http://www.scopus.com/inward/record.url?scp=79959661944&partnerID=8YFLogxK
U2 - 10.1002/chem.201100457
DO - 10.1002/chem.201100457
M3 - Article
C2 - 21626585
AN - SCOPUS:79959661944
VL - 17
SP - 7739
EP - 7744
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 28
ER -