Sinistrose

In the early 80s when I was in high school I used to read Omni magazine. This was when it first came out; later, it transformed into a highly sensationalistic purveyor of "paranormal" ideas, and lost all its credibility, but at first it was more futurist and science-fiction oriented. One part of the magazine had brief articles about possible advances in science and technology; as many of them were very cutting-edge they often never saw the light of day, but that's the price you pay for getting the most advanced news about speculative research.

At the time artificial sweeteners were big in the news, with talk about aspartame's safety, and frequent references to saccharine and cancer. One issue I found an article speaking of an interesting idea that someone was pursuing, which was described as "left-hand sugar".

The idea as I recall it is that the three-dimensional shape of a sugar molecule can be reversed as in a mirror (a change of its chirality, though the article didn't mention that word) to produce a new compound. This would have precisely the same chemical characteristics of sugar in two important key respects: it would taste the same (not just very similar, as in most artificial sweeteners, but identical), and it would work the same in recipes (browning, caramelizing, having the same density, etc.) However, because the enzymes in your stomach only face one way, it would be entirely indigestible. (The article didn't talk about any possible impact on your digestive system, which is the one possible fly in the ointment.)

All that was needed, the article suggested, was a way to manufacture the stuff affordably, and it would become the perfect artificial sweetener, and drive the alternatives out of business in one fell swoop.

Though the article only called it "left-hand sugar", alluding to the common practice of referring to opposite-chirality chemicals with the term "left-handed", I couldn't help notice that dextrose shares a linguistic origin with "dexter", which means right-handed. Therefore, I reasoned, this compound would have to be named sinistrose. (Except marketing would never let that happen. "Sinister" means "left-handed", and has taken on its modern meaning only due to prejudices against left-handedness as being strange and therefore probably bad.)

And then I never heard anything about this stuff again. Over the years I've occasionally tried to find something out about it. I could never find the original Omni article, nor any references to it (this is not that unusual: there are a few other things from Omni at the time I remember but can't find). And no attempts to look up what came of this, based on what little I remember, have panned out.

For a while I thought that the "invert sugar" I was seeing on some products might be it, and I only wondered why it wasn't being used more widely. But no, it turns out invert sugar is a whole other thing.

My best guess is that it turns out that left-hand sugar isn't really all that that article made it out to be. Maybe it is digestible, or maybe its indigestibility is a big problem, or maybe it doesn't really taste and work the same (there's no reason why the enzymes in your gut have to be single-chirality while the receptors on your tongue wouldn't be; if that's so, it's just coincidence), or maybe they couldn't make it work, or maybe the makers of one of the other artificial sweeteners bought and shelved the idea (tempting like all conspiracy theories but unlikely -- why wouldn't they use it to put their competitors out of business?).

Still, I wish I could find out the answer. But I just don't know what to search on. I have found a few references to "L-sugar" (see for instance here) but nothing that talks about it as the savior of the artificial sweetener concept, or why it isn't that. It seems certain that the dewy-eyed optimism of that early Omni article didn't pan out, and that's not too surprising, but I can't find anything about why.

Or why no one but me seems to have thought of the name "sinistrose".