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Duke chemist has new way to tell right from left
Date:6/5/2008

DURHAM, N.C. A Duke University chemist has apparently solved a long-standing frustration in creating certain synthetic molecules that make up drugs, which could lead to better drugs with fewer side effects.

Like human hands, many molecules that make up drugs come in two shapes, right and left. But usually only one of the two versions has the desired effect; the other is at best useless and sometimes even harmful. For example, side effects from the morning sickness drug Thalidomide resulted in profound birth defects because one shape of the molecule was therapeutic and the other was dangerous.

Don Coltart, an assistant professor of chemistry at Duke, appears to have found a way to make synthetic ketone molecules in just one version or the other using a process that is faster, cheaper and less wasteful than the best techniques now available.

And unlike previous attempts to make just one shape of these molecules, a process called asymmetric synthesis, the new method should be able to scaling up to industrial manufacturing quantities.

"Asymmetric synthesis of ketones is not new, but we can do it more practically and easily," said Coltart, who developed the new technique with graduate student Daniel Lim."

Though well-known to the pharmaceutical industry, this problem of molecular handedness in ketones has been difficult to solve. Academic labs have succeeded at asymmetric synthesis over the last two decades, but only by using extreme conditions (e.g. temperatures of -100 degrees Celsius), and costly and time-consuming steps.

Conducted at zero C to -40 C, the new process uses a small molecule called a "chiral auxiliary" to attach pieces to a molecule being built, which causes the new pieces to have the correct handedness. The process is up to 98 percent accurate, Coltart said, and the auxiliary molecules can be easily released and recycled after they've done their work.

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Contact: Karl Leif Bates
karl.bates@duke.edu
919-681-8054
Duke University
Source:Eurekalert

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