Related Experiment Video
Updated: Jan 22, 2026

Experimental Models to Study the Neuroprotection of Acidic Postconditioning Against Cerebral Ischemia
Published on: July 31, 2017
Stereoselective semi-synthesis of the neuroprotective natural product, serofendic acid
Dimitri Perusse1, Michael J Smanski1
1Department of Biochemistry, Molecular Biology, and Biophysics , BioTechnology Institute , University of Minnesota , Twin Cities , Saint Paul , MN 55108 , USA .
Abstract:
We have recently demonstrated a synthetic biology-enabled semi-synthesis of the potent neuroprotective compound, serofendic acid. An engineered bacterium produces ent-atis-16-en-19-oic acid, which has six of eight chiral carbons configured with the appropriate stereochemistry. Setting the configuration of the C15 hydroxyl group and C16 methylene is a critical step that occurs late in each published total or formal synthesis. Here we explore the use of alternative reducing reagents, stereochemical directing agents, reaction order, and product recycling to improve the diastereoselectivity of this step. We find that installing and oxidizing the C17 methylsulfide prior to reducing the C15 ketone provides the greatest yield of the desired C15,C16 diastereomer. This represents an improved total synthesis of serofendic acid.
Related Concept Videos
Products of the Citric Acid Cycle
Synthesis and Decomposition Reactions
What is Natural Selection?
Nature and Nurture
Amino acids
Transfer RNA Synthesis
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...

