Cyclization of synthetic seco-proansamitocins to ansamitocin macrolactams by actinosynnema pretiosum as biocatalyst

authored by
Kirsten Harmrolfs, Marco Brünjes, Gerald Dräger, Heinz G. Floss, Florenz Sasse, Florian Taft, Andreas Kirschning
Abstract

Ring closure is possible with seco-proansamitocin and two activated SNAC esters, which can be processed to ansamitocin P3 and 19-deschloro-20-demethoxy AP-3, respectively, by an AHBA-blocked mutant of Actinosynnema pretiosum. This work sheds light on the synthetic potential of macrolactamizing amide synthases. The new ansamitocin derivative showed similar to enhanced antiproliferative activity against several cancer cell lines relative to AP-3.

Organisation(s)
Institute of Organic Chemistry
Centre of Biomolecular Drug Research (BMWZ)
External Organisation(s)
University of Washington
Helmholtz Centre for Infection Research (HZI)
Type
Article
Journal
ChemBioChem
Volume
11
Pages
2517-2520
No. of pages
4
ISSN
1439-4227
Publication date
10.12.2010
Publication status
Published
Peer reviewed
Yes
ASJC Scopus subject areas
Biochemistry, Molecular Medicine, Molecular Biology, Organic Chemistry
Sustainable Development Goals
SDG 3 - Good Health and Well-being
Electronic version(s)
https://doi.org/10.1002/cbic.201000422 (Access: Unknown)