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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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December 1, 2011

Nevirapine: Not Chiral. Paper: Not Right. Editorial Staff: Not Doing Their Job

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Posted by Derek

Readers may remember a now-retracted paper that I first blogged about here, the one that claimed to have isolated the reverse transcriptase inhibitor nevirapine as a natural product. Moreover, it claimed that the isolated material was chiral, which would have been very interesting indeed if it were true. (And, as that last post says, would have been worth making a big point of, if the authors really had understood what they were claiming).

Now a group from Manchester has weighed in on that topic. And what they find is what anyone who'd examined the field should have expected: that the nevirapine molecule, although capable of existing in two chiral forms, equilibrates between them on a time scale of seconds at room temperature. Isolating the atropisomers by standard means is not possible.

So everything about that original Tetrahedron paper was wrong; it never should have made it through the review process. And that's why I highlight such things - not to heap scorn on the original authors, which doesn't do that much good, but to heap it on the people who let such papers into print. Reviewers and editors are supposed to notice when a paper has made very unusual claims, and they're supposed to ask the authors to back them up. But the folks at Tetrahedron were asleep at the switch when this one came through. It's important for them (and other editorial staffs) not to let that happen, and it's important for a journal's readers to realize that it can.

Addendum - as an aside, I note that one of this blog's entries (the second link above) is cited in the references of this latest paper. I'm glad to be a cite-able source!

Comments (8) + TrackBacks (0) | Category: Natural Products | The Scientific Literature


1. MTK on December 1, 2011 9:15 AM writes...

I'm not sure if it's due to the blogosphere or what, but there certainly seems to be more cases than ever of poor reviewing and editing occurring within the literature. Much like the news maybe it's just a case of us learning about this instances more often due to increased communication through the internet, but I can't help but think that the increased # of journals and the increased emphasis on speed of publication (ASAP articles, accepted manuscripts online, etc.) has made this type of thing more common.

Perhaps, however, we're just slow to adapt our behaviors to match the new realities. As more people are exposed as sloppy, incorrect, or fraudalent (as authors, reviewers, and editors) things will change and we'll all begin to take those tasks more seriously.

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2. partial agonist on December 1, 2011 9:42 AM writes...

Kind of remarkable reading throught he thread and looking at the paper.

Many of us reached the proper scientific conclusion, that a barrier exists but no way would it be large enough to give discreet persistant enantiomers at room temperature,

and also reached the proper conclusion that the original paper was shoddy, should be withdrawn, and that the authors seemed to not realize the significance of their claims

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3. pdf on December 1, 2011 10:12 AM writes...

And Tetrahedron even charges $41.95 to read a retracted paper. I thought a retracted paper should mean to disappear forever, or at least leave it available for free since it’s worthless anyway.

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4. Ed on December 1, 2011 10:18 AM writes...

I find it somewhat amusing that this debunking apparently took the work of five people. Talk about journal proliferation - another issue here is "author" proliferation.

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5. coprolite on December 1, 2011 2:10 PM writes...

Nice one on the addendum, Derek!

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6. ArmedAndDangerous on December 2, 2011 1:25 AM writes...

the fact that they isolated nevirapine as a "natural product" should give pause in itself. countless pharmaceuticals have been found as low-level environmental contaminants (particularly very hydrophobic ones, like benzodiazepines)

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7. Nick B on December 2, 2011 12:59 PM writes...

pdf: While that might seem like a good idea to make it free, that would then mean that bad science is more accessible than good science. It is also a bad idea to disappear a paper. It is still educational to have access to such papers, and there may be data reported in them that is useful, even while it does not support the conclusions reached, etc.

As long as such papers always have a big "RETRACTED" notice and a link to the description of why it was retracted, there's no harm in keeping them around.

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8. cliffintokyo on December 5, 2011 3:44 AM writes...

Excellent comments.
You would think that peer review would improve with e-reviewing - more time to spend doing a thorough job without worrying about meeting postal deadlines.
Or am I missing something?

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