A Highly Convergent Synthesis Route for Adda: A Non-Proteinogenic Amino Acid Unit in Cyanobacteria

2025/08/01 by Meher K. Prakash, Naresh M. Venneti, Judy A. Westrick +1 · 1 voice
Medicine · Chemistry · Biochemistry, Genetics and Molecular Biology · #Microbial Natural Products and Biosynthesis #Chemical synthesis and alkaloids #Chemical Synthesis and Analysis

paper · doi:10.1021/acs.joc.5c01357

openalex publication_date 2025/08/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/24

Abstract

We report a concise nine-step synthesis of Boc-Adda-OH, a key residue in bioactive cyanobacterial peptides. The route features a regio- and stereoselective intermolecular Heck reaction to form a stable isoxazolidin-5-one, followed by N-O bond cleavage. This efficient, convergent approach offers excellent stereocontrol and functional group tolerance, facilitating access to Adda for natural product synthesis, environmental monitoring, and toxicological studies.

Discussions

• The Kodanko Lab report a concise nine-step synthesis of Boc-Adda–OH, a key residue in bioactive cyanobacterial peptides in The Journal of Organic Chemistry. #wsuchemistry #ResearchInDetroit #ChemSky [bsky, 2 points, 0 comments]

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