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Abstract
AbstractPseudo‐natural products (PNPs) combine natural product (NP) fragments in novel arrangements not accessible by current biosynthesis pathways. As such they can be regarded as non‐biogenic fusions of NP‐derived fragments. They inherit key biological characteristics of the guiding natural product, such as chemical and physiological properties, yet define small molecule chemotypes with unprecedented or unexpected bioactivity. We iterate the design principles underpinning PNP scaffolds and highlight their syntheses and biological investigations. We provide a cheminformatic analysis of PNP collections assessing their molecular properties and shape diversity. We propose and discuss how the iterative analysis of NP structure, design, synthesis, and biological evaluation of PNPs can be regarded as a human‐driven branch of the evolution of natural products, that is, a chemical evolution of natural product structure.
Highlights
Fragments in novel arrangements not accessible by current biosynthesis pathways
We provide a cheminformatic analysis of Pseudo-natural products (PNPs) collecsampling of chemical space offered by fragment-based compound design.[15]
New pseudo-natural product (NP) scaffolds preferably have a high degree of three-dimensional character, as chirality and stereogenic content contribute to biological relevance and bioactivity.[25,26,27]
Summary
New pseudo-NP scaffolds preferably have a high degree of three-dimensional character, as chirality and stereogenic content contribute to biological relevance and bioactivity.[25,26,27] To provide structurally distinct pseudo-NPs, NP-derived fragments with complementary heteroatom content may be combined (e.g. N and O). During the period of 1999 to 2000, she applied her knowledge in an employment at Evotec Biosystems AG and in 2001, moved to the University of Leipzig as a junior research group leader She received her habilitation from the TU Braunschweig in 2004 before she joined the TU Dortmund’s Faculty of Chemistry and Chemical Biology. An example can be seen when comparing pyrroquinolines 16 and 17 These connectivity patterns have been identified, and can be exploited for the combination of more than two NP-derived fragments at a time (Figure 2, Panel C, Design Principle 3). Taken together, these design principles can be used to reveal unexplored areas of chemical space with potentially high bioactivity value
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