L-arabinose is a thing and it's natural. Only really available in Japan though. Might give you some gas because some bacteria can break it down, but probably not as bad as xylitol, erythritol, etc.

Doesn't allulose work pretty much the same way?

Ooh, I should try that sometime

It's pretty awesome in terms of taste - it's just a bit less sweet but tastes just like sugar. I didn't find too much info on impact but it seems pretty safe. And you can really use it as a sugar, it even caramelizes. I use it to make home made sugar free ice cream with real sugary consistency. But for me personally, having too much of it make my stomach rebel.

Yeah I think arabinose is likely to have less of a GI effect (I have eaten some from the lab on a whim) but I can't find any references on this.

The GI effect should be just directly correlated with how well large intestine microbiome can ferment these, IIUC? And I guess also with how much you need to have equivalent taste of 1 g sugar.

As in, if it tastes sweet but is not absorbed in the small intestine, so has "no calories", it will inevitably all pass on to the large intestine where it can be fermented.

As someone who absolutely hates the synthetic taste of aspartame etc. but has to stay on a low-FODMAP diet, I've just resigned to eating stuff with ordinary sugar and using sufficient moderation.

According to the big W, part of it is due to inhibiting digestion of normal sugar, which tracks my understanding of chemistry. So there's a lot of factors.

I would imagine that if humans did use it at scale, it wouldn't be long until the microbiome was evolving to metabolize it.

Do you use an ice cream maker?

Yeah. I can't say that I've gotten to professional quality but I'm a bit lazy with the recipes.

I also love Allulose for ice cream. It costs around $25 for 2lbs bag from Amazon, that lasts us 2-3 months. It doesn't have that "fake sugar" taste, or the weirdness you get with some of the alcohol sugars (my wife once made cookies that were "cold" when you ate them because of the sugar alcohol, it was a really weird sensation.

We got a Ninja Creami, it's not a traditional ice cream maker, you freeze these pint cups, then run them through the machine and it shaves it then blends it. My preferred recipe is: a quarter cup 0% yogurt, 2-4tbs allulose, pinch of xantham gum, the remainder fruit (strawberry, blueberry, canned low sugar pears or mandarin oranges or pineapple or peaches). This is delicious, low calorie (140-240cal per pint), and low sugar. It hits all the "ice cream" centers in my brain.

My wife takes it much fancier, she will make a vanilla base, and then often make low sugar mix ins (fudge, choc chips, caramel (with allulose), peanut butter cups (with PB2), marshmallows).

The Creami is noisy as hell for 3 minutes, and I wasn't sure how much we'd actually use it, but we've used it a lot. We got it on sale, about half price, which made it easier. Woot sometimes has them about this price (more like $100 than $200). One down side is that you basically have to re-blend it every time you want some, the remains largely freeze back into solid, though if you hit it with the microwave for 20 seconds you can kind of chunk it up and eat the flakes. Not really ice cream at that point.

It's not legal yet in Europe, but can't wait to try it out!

It's available in the UK but it's quite expensive. Sold as a pre-meal supplement from what I can tell.

Kinda weird to be downvoted for the above. GP said L-arabinose's available in Japan only. I responded to that. Could one of the downvoters please at least let me know what about my comment was so bad?

For reference, here's one place that sells it in the uk [0]. It's made in the UK as well.

Directions are:

    Take 2g of Powder approximately 30 minutes before main meals.

Which matches the second part of my post (pre-meal supplement).

[0] https://www.sweetcures.co.uk/products/l-arabinose-original-p...

I am not your downvoter, but after upvoting on my phone a few times I started to realize it wasn't really clear whether my fat finger hit the up arrow or the down arrow; there is not clear feedback[1]. Since then, I've found myself concerned I might have downvoted a post I really liked, so I unvote, zoom in, and revote. Even then sometimes I've remained unclear/nervous and had to zoom yet again. I'm not sure others are aware of this UI issue or make the effort in this regard.

This is a non-issue on my laptop where the cursor is quite visible and precise.

[1] Writing this post encouraged me to experiment. I guess if you vote up, you get an option to "unvote" but if you accidentally downvote, the option is to "undown". So there is more visible feedback about your vote than I was aware of. I will probably look for that going forward to ensure my voting intention was properly registered. But it's not super-obvious.

I've done the same thing. Now whenever I intend to upvote I always zoom in to make sure I'm hitting the correct arrow!

I can recommend using the “hack” app to read HN on the phone. Voting is done by swiping, so it’s much easier to avoid unintended downvotes.

(edit: I don’t know if it’s available on android, though. I’m an iphone user myself.)

After you vote you have a new option. If you upvoted the option says "unvote". If you downvoted it says "undown". Just check the text after you vote to make sure you didn't fat finger it.

Thanks for the info!

Any good sources you know of? Unless we are talking crazy expensive I feel like it could be pretty useful for a lot of home recipes. I don't make that much sugary stuff anyway. Does it caramelize like normal sugar when heated?

I would be surprised if it didn't caramelize. I don't know of any good sources, sorry.

it does. it behaves identically to regular sugar except in how it interacts with other organic compounds.

$110/KG here

https://www.scbt.com/p/l--glucose-921-60-8?lang=en&cur=usd&s...

Another alternative is duox-matok's technology, that increases the surface area of sugar or something similar, and this allows to use 30%-50% less sugar for the same sweetness effect.

Just for clarification, are you implying L-arabinose is the left-handed isomer of glucose?

Interesting! https://en.wikipedia.org/wiki/L-Glucose

"L-Glucose was also found to be a laxative," perhaps another factor in it's adoption.

In what quantities? Often these tests use implausibly large amounts.

I’d imagine it works like lactose, and if that’s the case a “regular” dose will do plenty.

It is the same/similar mechanism as the infamous sugar free gummy bears.

https://www.healthline.com/health/food-nutrition/sugar-free-...

If you are looking for high speed mass discharge a heaping teaspoon of xylitol or maltitol (what is in sugar free gummy bears) plus coffee will do the trick within 15 minutes.

Be warned that you risk serious dehydration and/or electrolyte imbalance if you try this.

What's used medically for this purpose (e.g. before a colonoscopy) is an osmotically balanced solution of polyethylene glycol, typically referred to as Macrogol.

Takes a couple of hours of continuous sipping, close to 1 liter total for an adult to get everything flushed, then you'll be discharging almost clear fluid by the end.

> Be warned that you risk serious dehydration and/or electrolyte imbalance if you try this.

A bit dramatic, considering these are widely food additives to things like gummy bears in similar amounts and stories abound about their effect.

A one time event is unlikely to do too much damage unless you’re already sick.

People should generally not be taking laxatives repeatedly for a prolonged period unless they have a prescribed indication.

> an osmotically balanced solution of polyethylene glycol, typically referred to as Macrogol.

It’s quite common in the US to do plain old miralax and G2 gatorade for outpatient colon prep. There is some controversy about this. But there isn’t much evidence that “osmotically balanced” (the whole concept of osmotic balance is suspect for an osmotic laxative - that works because of its inherent imbalance) has any meaningful benefit other than selling something that sounds good with little evidence.

https://my.clevelandclinic.org/health/articles/21217-miralax...

People that get into trouble are typically abusing laxatives or have chronic kidney, liver or heart disease that put them at risk.

Just get up in the morning and chug a liter of water and then have a cup or two of strong coffee ?

This is the source they used: https://www.giejournal.org/article/S0016-5107(03)01304-X/ful...

Does was 24 grams. For reference, a 12 ounce can of coke has 39 grams of sugar.

However, this was not a double blind study, so mileage my vary.

Certain sugar substitutes are laxatives. I had some DELICIOUS sugar free gummy worms from a cracker barrel that gave me the worst shits for a few hours. I only ate like 10-15 of them.

Osmotic laxatives such as lactulose need only 10 grams or so for “effect”. Standard dose of say lactulose for cirrhotics is about 20 grams multiple times per day to keep them shitting.

So wait, is this another Olestra? Guess it depends on what kind of response you get in the gut.

Actually that likely means there is a microbiome component, unfortunately

Or just an osmotic effect.

Holy grail of sweeteners

Why not make both isomers and feed them to bacteria? Only left-handed remains.

It's gotta be something more to than that, even 50-50% sugar would be a great product in its own right.

Maybe the problem is more with synthesizing sugar without biological help. After some cursory googling, it sounds like many artificial sweeteners are several orders of magnitude "sweeter" than table sugar, so you'd have to synthesize far more L-sucrose to get a similar effect.

True, you'd need tablespoons of it. :-/

It seems with all the bacteria out there it seems like there would be one that does something obnoxious with L-sucrose.

Fructose is about 50% sweeter than sugar (sucrose), so you can save calories by substituting 2/3 of the quantity of sucrose with fructose

Fructose is metabolised differently IIRC and carries greater risks if anything, possibly this is why HFCS is worse for you.

HFCS isn't particularly high in fructose. Sucrose is essentially 1:1 fructose to glucose. HFCS is typically either 42% or 55% fructose, the rest glucose, so basically the same. Honey and agave nectar are also similar.

I can't say I'm an expert, but I haven't seen anything where consuming fructose is worse overall than other sugars. Fruits for example also tend to be high in fructose, and if you're going to have sugars they tend to be one of the best ways.

Because we have effectively infinite amounts of d-glucose in the biosphere and that's incredibly hard to compete with on cost.

Also there's more than one stereocenter in "generalized glucose"

if we could make racemic glucose (i.e. a 50:50 split of D/L-glucose), the battle would be done.

you'd expect to see this if we had a purely synthetic process for the creation of glucose in the lab. but, as far as i know, we only have other biological processes that produce glucose, and as such, only produce the one isomer.

It is 100% possible to make glucose synthetically, racemically or otherwise. I believe it was done in the 60s and iirc sharpless used sugar synthesis to demonstrate the power of asymmetric epoxidation (which he won the Nobel for).

It is however very not economical to do so

I've seen the economics talked about a few times in this thread but having no experience at all with the industry - what is the difference between economical and not in actual dollar values?

If you were to produce a KG of this vs say our common art-sweetners what is the cost multipler

Well keep in mind that stuff like sucralose may be more expensive to make but it's also selected because it's way more potent, so there's a lot of filler (usually cyclodextrin?) To fill out a packet and make a cooking/flavoring equivalent.

Though I'm not 100% sure maybe sucralose is made by enzymatically installing those halogens? I could be very wrong.

Speaking of filler, it seems the experiment in question didn’t control for that? Since there’s so little artificial sweetener is it possible the gut flora are reacting to the filler?

The experiment in the article explicitly does control for this

> The participants (20 per group) were given sweetener packets of aspartame, sucralose, saccharin, or stevia, each bulked out with glucose to an equivalent size, with another group that got just glucose and another group that took no sweeteners at all.

In this experiment, the artificial sweeteners used glucose as the filler. They also account for the effects of the glucose filler on the insulin response in all groups by measuring the difference in the response.

My guess is a minimum of 5-10x more expensive at scale.

Sugar is really cheap, especially if you don’t mind which particular local source you use (sugar cane, corn syrup, etc).

Just a heads up: you seem to be shadow-banned, all your posts are flagged.

His post looks normal to me...

Apparently he got unshadowbanned recently.

I vouched for a couple of them; the others are still dead.

insidious

What posts? It shows empty for me.

Do we know that it doesnt have an effect on gut-biome though?

There would be none:

"..but cannot be used by living organisms as a source of energy because it cannot be phosphorylated by hexokinase, the first enzyme in the glycolysis pathway. "

https://en.wikipedia.org/wiki/L-Glucose

EDIT: Ok, yeah, sorry. I'm sure some bacteria out there could do something with it and make you have an upset stomach. But it's not very likely.

Nature laughs at "not very likely".. We gotta get used to this as a species.

Too bad the theoretically cheapest way (mirror-image microorganisms) is an enormous ecological risk.

Can you please elaborate on this? I tried googling it and just got a lot of seemingly unrelated stuff.

Mirror image microorganisms process and produce molecules of opposite normal chirality as a result of their metabolism. Since there's no a priori reason why life should prefer either left handed or right handed molecules, the way we got here is the result of the first proto-metabolic processes billions of years ago just happening to choose what we use today. If we introduced mirror image microorganisms into the ecosystem, the danger is they could outcompete existing organisms while simultaneously contaminating the environment with their mirror-image waste products.

in tl;dr scifi parlance, we could make it so that we'd have bountiful food and starve because we turned earth into an alien planet

Who you calling "we", l-grogenaut?

Presumably they would be poisoned by the large amount of right handed biochemistry thats everywhere already.. It might be super hard to keep them alive in nature at all.

But if youre in the lab and thinking about it could ya whip us up some C-F eating/mineralizing micros? Talk about whats poisoning the biosphere..

Wouldn't they be at a strict disadvantage because they cannot eat other typical-chirality-producers for resources?

I think the idea is that we would keep them in a lab and feed them whatever works.

For anyone interested in this concept, without spoiling too much, you should read the sci-fi book Starfish by Peter Watts. He has the entire text of the book up for free on his website, in glorious 1990s handcrafted HTML: https://www.rifters.com/real/STARFISH.htm

Thanks so much for breaking it down - fascinating topic!

I am also interested to know that!

Curious, did you remove the green goo post because you found something wrong with the reasoning or did you judge it to be an infohazard?

Microorganisms generally eat glucose, it's plants that make them.

Is there any way to do this (safely) in small batch?

I thought L-glucose and D-glucose would interconvert in water? They will reach an equilibrium with both present?

D-fructose and D-glucose interconvert in basic environment. You cannot convert L-glucose to D-glucose and vice-versa.

I never see much in replacing Sucrose with normal Glucose. Never understood why.

Forgive my ignorance, but couldn't consuming opposite chiral chemicals eventually lead to developing prion diseases?

Is there any evidence that would indicate that this has ever occurred? The way I think about these things is in terms of where the electron density tends to be, what fits into what, how things get recycled inside our cells (Ubiquitin, Cytochrome P450, etc.), so on and so forth. It has been awhile since I looked, last I checked, we don't know how badly-folded prions spread the pattern to other prions. I'd love to know if there is any news on that.

Given the above, I would guess that there's no link at all between the two. I could just be very wrong or behind the times.

Can you elaborate this please?

> going to be fucking rich

It is the year 316720, and the majority of intergallactic trade is in left-handed and right-handed sugar.

Glucose is also known as dextrose for its dextral (right-handed) chirality. Which means that left-handed glucose should be sinistrose. What a name!

It's actually levorotatory glucose not sinistrose. It's derived from the Latin word "laevus" for left and its shortened form is "levo".

Could you synthesise the mix but not separate the isomers, for sugar with 50% of the calories? Still too expensive?

Cool, but sugar (sucrose) is actually glucose+fructose.

Is there a calorie-free fructose isomer?

ironic how the post suggests they are not entirely harmless and you suggest a holy grail that we don't know much about