# Left-handed sugar? **URL:** \ **Category:** Factual Questions\ **Created:** [January 16, 2009, 5:52pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623 "2009-01-16T17:52:05Z")\ **Posts on this page:** 18\ **Page:** 1
**Author:** ![campii](https://avatars.discourse-cdn.com/v4/letter/c/eb8c5e/32.png) [@campii](https://boards.straightdope.com/u/campii)\ **Post date:** [January 16, 2009, 5:52pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/1 "2009-01-16T17:52:05Z")
What ever happened to the “left-handed” sugar project? Campy ---
**Author:** ![Squink](https://avatars.discourse-cdn.com/v4/letter/s/b5e925/32.png) [@Squink](https://boards.straightdope.com/u/Squink)\ **Post date:** [January 16, 2009, 6:05pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/2 "2009-01-16T18:05:49Z")
Which left handed sugar project? ---
**Author:** ![beowulff](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/beowulff/32/542_2.png) [@beowulff](https://boards.straightdope.com/u/beowulff)\ **Post date:** [January 16, 2009, 6:12pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/3 "2009-01-16T18:12:15Z")
Are you thinking of [Tagatose](http://en.wikipedia.org/wiki/Tagatose)? ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [January 16, 2009, 6:14pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/4 "2009-01-16T18:14:02Z")
There was talk about developing a left-handed sugar that would taste as sweet as regular sugar but would not be recognized and absorbed by the intestines, thereby making it zero calories. It was called tagatose and marketed as [Naturalose](http://www.tagatose.com/). Here’s a 2004 [Wired](http://www.wired.com/wired/archive/11.11/newsugar_pr.html) article about it. The runout of the patent, difficulties in regulatory approval, and lack of price equivalence are big hurdles. ---
**Author:** ![DrFidelius](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/drfidelius/32/3447_2.png) [@DrFidelius](https://boards.straightdope.com/u/DrFidelius)\ **Post date:** [January 16, 2009, 6:17pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/5 "2009-01-16T18:17:47Z")
Serious answer done? Good. They found it caused everyone to turn into their evil mirror-universe counterpart. Men spontaneously grew beards and women showed much more cleavage. They pulled it from the market rather than risk the economic domination of the world by leather clothing suppliers. ---
**Author:** ![Lobsang](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/lobsang/32/4067_2.png) [@Lobsang](https://boards.straightdope.com/u/Lobsang)\ **Post date:** [January 16, 2009, 6:29pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/6 "2009-01-16T18:29:20Z")
:dubious: ---
**Author:** ![yabob](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/yabob/32/2821_2.png) [@yabob](https://boards.straightdope.com/u/yabob)\ **Post date:** [January 16, 2009, 7:21pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/7 "2009-01-16T19:21:17Z")
A note - tagatose, strictly speaking, is not a left-handed sugar. It just acts like one. As noted in the wiki article: > [@](#): > > Gilbert Levin upon learning about chirality, had the idea to search for a left-handed sugar. Cycling through the various left-handed sugars, he was accidentally sent D-tagatose, structurally similar to L-fructose. Even though Levin thought that his answer to a sweetener would be found in a left-handed sugar, it was the right-handed molecular form that proved to be a winner. FDA approved tagatose as a food additive in October 2003. D-tagatose occurs naturally in low concentrations, and Levin’s company (Spherix) developed a process for extracting it from whey. AFAIK, actual left handed sugars all have to be synthesized, which makes them too expensive to be commercially viable. I followed the story on tagatose with some interest several years ago. On the surface, it appears ideal. It hasn’t really taken off, though, and I suspect it’s still too expensive. You have to process a lot of whey to get a little bit of tagatose. The legal fights between Spherix and Arla foods didn’t help either. SPEX is strictly a research outfit with no manufacturing facilities, and a woefully undercapitilized penny stock operation at this point. ---
**Author:** ![dtilque](https://avatars.discourse-cdn.com/v4/letter/d/d6d6ee/32.png) [@dtilque](https://boards.straightdope.com/u/dtilque)\ **Post date:** [January 17, 2009, 7:47am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/8 "2009-01-17T07:47:39Z")
> [@Lobsang](#): > > :dubious: [Mirror, Mirror](http://memory-alpha.org/en/wiki/Mirror,_Mirror_(episode)) ---
**Author:** ![Jinx](https://avatars.discourse-cdn.com/v4/letter/j/c6cbf5/32.png) [@Jinx](https://boards.straightdope.com/u/Jinx)\ **Post date:** [January 17, 2009, 10:40am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/9 "2009-01-17T10:40:27Z")
> [@yabob](#): > > A note - tagatose, strictly speaking, is not a left-handed sugar. It just acts like one… I posted the same question about the “left-handed sugar” WAGing that’s what Splenda is. I recall getting this same response how it, too, is not really a left-handed sugar. I guess I’ll go ask Mr. Owl…the world may never know! 😉 ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [January 17, 2009, 4:15pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/10 "2009-01-17T16:15:22Z")
Splenda or sucralose is not a left-handed sugar in any way. It uses regular sugar and modifies it by adding chlorine atoms. Not even conceptually similar. ---
**Author:** ![yabob](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/yabob/32/2821_2.png) [@yabob](https://boards.straightdope.com/u/yabob)\ **Post date:** [January 17, 2009, 5:06pm UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/11 "2009-01-17T17:06:55Z")
Which is the reason sucralose has some of the same problems as other artificial sweeteners. It’s about 600 times as sweet as sucrose, and to be volume equivalent with sugar, they have to add a filler, such as maltodextrose. It leads to the physical properties not being the same as sugar, which affects baking and so on. D-tagatose is a sugar, albeit an oddball one, is very close to the same sweetness as regular sugar, and behaves the same physically - it carmelizes and so on. It’s just largely inert as far as your digestive system is concerned. ---
**Author:** ![Solfy](https://avatars.discourse-cdn.com/v4/letter/s/848f3c/32.png) [@Solfy](https://boards.straightdope.com/u/Solfy)\ **Post date:** [January 18, 2009, 2:36am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/12 "2009-01-18T02:36:44Z")
> [@yabob](#): > > AFAIK, actual left handed sugars all have to be synthesized, which makes them too expensive to be commercially viable. A vast majority of chiral molecules have an inexpensive naturally occurring/derived version, and a prohibitively expensive non-naturally occurring version. Take proline for example. Aldrich lists a kilo of L-proline for $447. If you want D-proline, 5g is going to cost $126. ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [January 18, 2009, 3:35am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/13 "2009-01-18T03:35:16Z")
This may be true for proline. However, it says nothing about sugars. Are there naturally-occurring left-handed sugars? Do they exist in any appreciable quantities? If not, what relevance is your point? ---
**Author:** ![Solfy](https://avatars.discourse-cdn.com/v4/letter/s/848f3c/32.png) [@Solfy](https://boards.straightdope.com/u/Solfy)\ **Post date:** [January 18, 2009, 3:56am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/14 "2009-01-18T03:56:22Z")
> [@Exapno\_Mapcase](#): > > This may be true for proline. However, it says nothing about sugars. Are there naturally-occurring left-handed sugars? Do they exist in any appreciable quantities? > > If not, what relevance is your point? My point holds for all chiral molecules. Not just sugars. Naturally occurring sugars/amino acids are cheap and readily abundant. Very frequently the other enantiomer is not easily obtained, and therefore expensive. If you have to synthesize something, it’s likely going to cost more than harvesting it from a field. ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [January 18, 2009, 5:07am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/15 "2009-01-18T05:07:29Z")
I get your point, that they do not necessarily have to be synthesized. I’m not disputing that. The processing of a natural sugar from other (cheaper and more abundant sugar) sources, yielding a product that is less sweet than sucrose is commercially a non-starter. Sucralose can work because it is 600 times sweeter. It’s of little matter whether you synthesize tagatose or process it from existing substances if neither route gets you to a commercial product since the reward isn’t commensurate with the price. That’s all I’m saying. ---
**Author:** ![Solfy](https://avatars.discourse-cdn.com/v4/letter/s/848f3c/32.png) [@Solfy](https://boards.straightdope.com/u/Solfy)\ **Post date:** [January 18, 2009, 5:46am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/16 "2009-01-18T05:46:50Z")
> [@Exapno\_Mapcase](#): > > I get your point, that they do not necessarily have to be synthesized. I’m not disputing that. > > The processing of a natural sugar from other (cheaper and more abundant sugar) sources, yielding a product that is less sweet than sucrose is commercially a non-starter. Sucralose can work because it is 600 times sweeter. It’s of little matter whether you synthesize tagatose or process it from existing substances if neither route gets you to a commercial product since the reward isn’t commensurate with the price. That’s all I’m saying. No no, what I was saying is that most odd molecules (left handed sugars, right handed amino acids) \*do \*need to be synthesized to obtain them in any reasonable quantity because they’re a rarity in nature. Or you have to perform an unreasonable amount of processing on a natural material to convert it. There’s no easy way to the uncommon enantiomers, and in that I believe we are in agreement. ---
**Author:** ![Little\_Nemo](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/little_nemo/32/3120_2.png) [@Little\_Nemo](https://boards.straightdope.com/u/Little_Nemo)\ **Post date:** [January 18, 2009, 6:04am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/17 "2009-01-18T06:04:29Z")
> [@](#): > > They found it caused everyone to turn into their evil mirror-universe counterpart. Men spontaneously grew beards and women showed much more cleavage. It said on the label there were possible side-effects. ---
**Author:** ![Malacandra](https://avatars.discourse-cdn.com/v4/letter/m/45deac/32.png) [@Malacandra](https://boards.straightdope.com/u/Malacandra)\ **Post date:** [January 18, 2009, 8:57am UTC](https://boards.straightdope.com/t/left-handed-sugar/481623/18 "2009-01-18T08:57:51Z")
> [@Little\_Nemo](#): > > It said on the label there were possible side-effects. Yeah, but usually they mean things like dizzy spells or a slight laxative effect. :dubious: