ArticleJournal of the American Chemical Society2005
Engineered biosynthesis of aklanonic acid analogues.
Article in Journal of the American Chemical Society, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 39 citations in OpenAlex.
- Article
- Rethinking Biosynthesis of Aclacinomycin A.Molecules (Basel, Switzerland) · 2023Review
- Biosynthesis of trioxacarcin revealing a different starter unit and complex tailoring steps for type II polyketide synthase.Chemical science · 2015Article
- Lomaiviticin biosynthesis employs a new strategy for starter unit generation.Organic letters · 2014Article
- Synthetic biology approaches in drug discovery and pharmaceutical biotechnology.Applied microbiology and biotechnology · 2010Review
- Cyclization of aromatic polyketides from bacteria and fungi.Natural product reports · 2010Review
- Biosynthesis of aromatic polyketides in bacteria.Accounts of chemical research · 2009Review
- Evolution of polyketide synthases in bacteria.Proceedings of the National Academy of Sciences of the United States of America · 2008Article
- Premithramycinone G, an early shunt product of the mithramycin biosynthetic pathway accumulated upon inactivation of oxygenase MtmOII.Angewandte Chemie (International ed. in English) · 2006Article
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
Aklanonic acid, an anthraquinone natural product, is a common advanced intermediate in the biosynthesis of several antitumor polyketide antibiotics, including doxorubicin and aclacinomycin A. Intensive semisynthetic and biosynthetic efforts have been directed toward developing improved analogues of these clinically important compounds. The primer unit of such polyfunctional aromatic polyketides is an attractive site for introducing novel chemical functionality, and attempts have been made to modify the primer unit by precursor-directed biosynthesis or protein engineering of the polyketide synthase (PKS). We have previously demonstrated the feasibility of engineering bimodular aromatic PKSs capable of synthesizing unnatural hexaketides and octaketides. In this report, we extend this ability by preparing analogues of aklanonic acid, a decaketide, and its methyl ester. For example, by recombining the R1128 initiation module with the dodecaketide-specific pradimicin PKS, the isobutyryl-primed analogue of aklanonic acid (YT296b, 10) and its methyl ester (YT299b, 12) were prepared. In contrast, elongation modules from dodecaketide-specific spore pigment PKSs were unable to interact with the R1128 initiation module. Thus, in addition to revealing a practical route to new anthracycline antibiotics, we also observed a fundamental incompatibility between antibiotic and spore pigment biosynthesis in the actinomycetes bacteria.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.