Bryostatin 1

November 06, 2017
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Macrolide lactones are natural products that have large, usually 14- to 16-membered, rings as their basic structures. They often have saccharide substituents, as in the antibiotics erythromycin and azithromycin.

The bryostatins are exceptions. They have 20-membered rings; and none of their substituents are saccharides. They occur in Bugula neritina, a species of tiny sea animals in the phylum Bryozoa. More than 20 bryostatins have been identified.

In 1960, chemist George Pettit, then at the University of Maine (Orono) isolated bryostatin 1 from B. neritina. Its structure was established in 1982; and subsequent research showed that it is a potent protein kinase C modulator. In clinical trials, it has shown activity against conditions such as cancer, HIV/AIDS, and Alzheimer’s disease.

It takes ≈1 t of bryozoans to isolate 1 g of bryostatin 1, so clearly an efficient lab synthesis is needed to pursue additional research. This year, Paul A. Wender and colleagues at Stanford University reported the shortest synthesis yet (29 steps!) of bryostatin 1. The previous record was almost twice that number. The compound is approved for use in human trials, but Wender believes that recently synthesized analogues may have greater medical value.

MOTW update

Triclosan, the Molecule of the Week for May 3, 2010, is a controversial antimicrobial agent that is contained in many consumer products. That year, the US Federal Drug Administration and Environmental Protection Agency began to examine its health risks. Since then, FDA ordered it removed from soaps and body washes by September of this year. 

Bryostatin 1 fast facts

CAS Reg. No. 83314-01-6
Molar mass 905.03 g/mol 
Formula C47H68O17
Appearance White solid 
Boiling point 230–235 ºC
Water solubility Insoluble
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