Timothy Jamison and his colleagues at the Massachusetts Institute of Technology (MIT) in Cambridge have developed a novel water-based technique for the rapid synthesis of previously expensive pharmaceutical related compounds. They were inspired by the red-tide algae's ability to produce large quantities of structurally similiar, toxic chemicals. The new rapid synthetis replaces the previous method which took dozens of person-years to produce just a few milligrams. The chemical in question is a long ladder moleclue containing adjacently bonded 6-member rings; its synthesis is troublesome because the base compounds (epoxy alchohols) tend to form 5-member rings. Dr. Jamison found that the addition of a 6-member ring "template" to an epoxy alchohol resulted in a cascade synthesis of 6-member ring ladders. As he puts it, "the trick is to give it a little push in the right direction and get it running smoothly." His team beleives that the red-tide algae uses an enzyme to catalyze the activation of the same cascade. Their findings may help produce new families of ladderlike compounds that could pave the way to novel drugs, including some showing promise for treating cystic fibrosis.The published synthesis technique for the valuable, 6-member ring, ladder molecules is available to any organic synthesis chemist.
Previous methods were labor- and energy-intensive and relied on reactions in toxic organic solvents. The new synthesis is water based and very rapid.
Long ladder molecules could be the backbone for new pharmaceuticals; however, research has been limited by the difficulty in producing even small quantities of the compounds.Edit Summary