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Total Synthesis of A54145 Factor D
Braden Kralt1, Ryan Moreira1, Michael Palmer1
1Department of Chemistry , University of Waterloo , 200 University Avenue West , Waterloo , Ontario N2L 3G1 , Canada.
The Journal of Organic Chemistry
|August 27, 2019
Summary
This study reports an efficient synthesis of A54145 factor D, a cyclic lipodepsipeptide antibiotic. The synthesis confirms the stereochemistry of a key residue and shows lipid tail configuration doesn't impact biological activity.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Biochemistry
Background:
- A54145 factor D (A5D) is a cyclic lipodepsipeptide antibiotic.
- Understanding its synthesis and structure-activity relationships is crucial for antibiotic development.
Purpose of the Study:
- To develop an efficient total synthesis of A54145 factor D.
- To confirm the stereochemical configuration of the MeOAsp residue.
- To investigate the impact of the lipid tail's stereocenter on biological activity.
Main Methods:
- Solid-phase peptide synthesis using 9-fluorenylmethoxycarbonyl chemistry.
- Attachment to 2'-chlorotrityl polystyrene resin.
- Off-resin cyclization and global deprotection.
Main Results:
- An efficient synthetic route to A5D was established, avoiding diketopiperazine formation.
- The MeOAsp residue was confirmed to have the 2S,3R configuration.
- The stereochemistry of the anteiso-undecanoyl lipid tail was found to have no effect on biological activity.
Conclusions:
- The developed synthetic strategy is effective for producing A5D.
- Stereochemical assignments for A5D have been confirmed.
- Lipid tail stereochemistry is not a critical determinant for A5D's biological function.
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