Related Experiment Video
Updated: May 23, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Ammosamide D, an oxidatively ring opened ammosamide analog from a marine-derived Streptomyces variabilis
Ende Pan1, Matthew Jamison, Muhammed Yousufuddin
1Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States.
Abstract:
Ammosamide D (1), an oxidized analog of the ammosamide family, was isolated from a marine-derived Streptomyces variabilis. Pyrroloquinoline containing alkaloids are a growing class of natural products, with 1 being the first example of an oxidized analog resulting in a 5,6-dioxo-5,6-dihydroquinoline ring system. Attempts at chemical conversion of ammosamide B to ammosamide D revealed that a strong chemical oxidant is required. Ammosamide D has modest cytotoxicity to the MIA PaCa-2 pancreatic cancer cell line.
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Antifungal Agents
Nomenclature of Primary Amines
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
