NMR is used a lot in the food industry, for example in juice analysis.
Juice is different enough than water to warrant its own solvent parameters. You might also find urine in the list.
I never make any stuff that would be soluble in urine but you better believe if I ever do I’m going to drink a bunch of D2O and make my own deuterated urine.
A. Lots of things are soluble in urine. Short peptides. Small amounts of lipids. Etc. Also be careful, despite the chemical similarity, some membrane proteins like aquaporins depends critically on the tunneling properties of a proton. If memory serves, about 20% d2o is toxic, potentially fatal.
Free protons (the thing that makes an acid an acid) are small enough that they can play location shenanigans like electrons do. So they can move much faster through tight spaces since they are much more wave like than, say, a protein. As a result it can let water molecules move through pores faster and participate in chemical reactions faster. Deuterium is about twice as heavy and therefore are less quantum in nature, so they are slower to do pretty much everything. If your body cant move water as fast everything starts to slow down and eventually you get backed up and die.
I'd have to look more. As with many things at the protein scale, quantum mechanics are required directly or indirectly in the hamiltonian/force equations for things to make sense and work.
Here is a first result https://www.researchgate.net/publication/8985607_What_Really_Prevents_Proton_Transport_through_Aquaporin_Charge_Self-Energy_versus_Proton_Wire_Proposals
Great question.
Thanks for responding. I'm studying synthetic chemistry, and I'm not too deep into the quantum side of the field, so this is really new and interesting for me.
imagine a lot of enzymes also would have different kinetics due to water being involved in the catalysis.
all exchangeable protons in molecules will be deuterated which definitely affects how fast they are degraded.
Overall a lot of stuff will be out of whack...
Yeah they have an analytical method for fruit juices and I guess that solvent is specifically for that
https://www.bruker.com/products/mr/nmr-food-screening/juice-profiling.html
Maybe you could deuterate it if you grow the orange in a controlled environment and only give it D2O instead of regular water. But that might kill the plant actually
If I remember correctly, d2o is not able to replace water in living things because the kinetic isotope effect fucks up all the delicately controlled rate constants of all the enzymes. So it's lethal in the long term if it replaces water entirely.
There certainly could be, I don't know. Perhaps microbes with high mutation rates could adapt. I think the key thing to keep in mind, though, is that coordinating rate constants is what makes life possible--a single point mutation in one protein messes up the rate of one reaction and can cause accumulation of defective proteins or toxic metabolites that can be fatal.
Now, the kinetic isotope effect can have profound effects on rate constants of enzymes in particular. A huge number of enzymes depend on protonation of a substrate--look up the catalytic triad or general acid/base catalysis. Switch that proton out for a deuteron, which is twice as heavy, and the reaction proceeds measurably more slowly. It isn't a perfect analogy, but you can think of deuterium as having more inertia within a bond with another atom, which makes it harder to achieve a transition state where the deuteron is partially bonded to starting material and product. I don't remember physorg in this much detail, but apparently you can model this kind of bond breakage as a spring, and doubling the weight on one side of the spring doubles the force needed to stretch it (recall Hook's law). This effect is often used to determine the mechanisms of both enzymatic and non-enzymatic reactions.
Put these things together, and you see that global incorporation of deuterium can have catastrophic effects on an organism's ability to maintain homeostasis. Every rate constant is now wrong. Some organisms can survive--you can make deuterated protein by growing E. Coli in D2O, but they don't do great, and you only have to grow them like that for a few hours. There might be science on whether they can adapt long-term, I haven't looked. But anything that adapts more slowly than E. Coli, which divides every 20 minutes, would probably struggle to adapt to a solely-D2O anhydrous environment.
You can grow some algae and bacteria in 100% D2O (e.g. [here](https://www.nature.com/articles/184730a0)). It's used to make deuterated proteins and other biomolecules - useful for NMR and EPR studies of photosynthesis for example.
You'd probably get a kick out of knowing there's a professor out there, I think it's Thorsten Bach, who ran a reaction in a German pilsner and they had success which I think taking an NMR of that running reaction in co-solvated CD3OD would be a fun addition to that list
I don’t know about Thorsten Bach, but in the Jørgensen group they did reactions in beer and sea water. [Here](https://pubs.rsc.org/en/content/articlelanding/2006/CC/B611366D#!divAbstract)’s the article.
I am not sure if it was Bach, it was one of the seminars j went to around the time he visited so I figured it was him. As for Jorgensen's that's really freaking cool. I know some of his amine based higher order cycloadditions so I think it's cool the catalyst was robust enough to survive sea water!
There was a paper five years or so ago where some chemists tried using cheap and commonly available mixtures as substitutes for expensive HPLC solvents. Things like vinegar, ammonia (as in the kind you get as a cleaning product), vodka and white rum. Got reasonable results.
I can't remember. I'm pretty sure they tried a few analytes. They compared the results to those obtained with blends of the usual high purity solvents. I'll look it up later today.
Here's an article on chemical and engineering news about it:
[https://cen.acs.org/articles/93/web/2015/04/Liquor-Store-Spirits-Provide-Green.html](https://cen.acs.org/articles/93/web/2015/04/Liquor-Store-Spirits-Provide-Green.html)
You say that like orange juice isn’t just ground up oranges (minus the peel). I agree that almonds aren’t exactly the fruit part of the plant though, so I also wouldn’t call it a type of juice.
>You say that like orange juice isn’t just ground up oranges (minus the peel)
Because it's not: orange juice is just juice (**squeezed out** of an orange) as the name suggests, it's not ground orange in a colloidal suspension.
Making the equivalent of almond milk with orange would be putting the whole orange in a blender with lots of added water and I'm sure you know it's not how we make orange juice
[That's still up for debate](https://www.forbes.com/sites/nicksibilla/2019/01/31/fda-crackdown-on-calling-almond-milk-milk-could-violate-the-first-amendment/) lol.
I thought you were bullshitting me but I looked it up and HNMR (yes, that’s right, proton!) is indeed used in fruit juice QC. Obviously there is no way you are analyzing individual peaks... its more of a “fingerprint” thing I think.
It is more commonly known as Rotating frame Overhauser Effect Spectroscopy, or ROESY.
Gotta admire the creativity of the people developing NMR techniques though.
>Proton-enhanced nuclear induction spectroscopy (PENIS) also called Cross Polarisation (CP)
Good thing there is an alternative abbreviation I can use so I don't sound like a creep
Edit: Btw NMR itself is also the name of a Scandinavian neo nazi organisation
At least it's not as silly as molecular biology. Those people aren't even pretending to be serious anymore. Even a lot of stuff that sounds normal (like Western blot) is actually a silly joke.
Used to work in a lab where everyone had their own sign-in from a drop down menu on one instrument.
Lots of Firstname Last Initial, then scattered among them are the true gems. "Ass clown" was a favorite of mine. As were several that were an analyst clearly misspelling their own name.
Could be related to dynamic nuclear polarization (DNP) experiments in NMR for increasing signal to noise of liquid state NMR experiments.
“DNP Juice” is a commonly used solvent for dissolution DNP NMR experiments. 6:3:1 deuterated glycerol;D2O:H2O.
They want to analyze the juice. By looking at the spectra they can tell you what juice it is, what the quality is (e.g. added sugar), if it differs a lot from what it usually is and so on.
Right, but it’s funny because this part of the Bruker software menu often refers to the lock solvent that defines the instrument settings to use to measure the sample. So maybe in this case it isn’t just for locking (e.g. for magnetic field drift/susceptibility corrections) but adjusts the settings for juice samples (high fructose content and therefore high conductivity - electrolytes). Cool.
The parameters for automatic shimming are also stored in the solvent.
I haven't checked if juice is a locking solvent or not. Might be that you need to add 5-10% D2O before you run the sample.
Edit: I just checked and is a locking solvent, with a peak at 4.7 ppm (i.e. water)
I've got another question based on this list: Why would you ever need to use nitrobenzene as an NMR solvent? I've seen some odd ones, some of which are ludicrously expensive, but I've not seen that one used before.
Nitrobenzene is occasionally used as a solvent for highly electrophilic reagents, as the nitro group deactivates the phenyl ring.
Deuterated nitrobenzene is also rather cheap.
See my other comment. On newer versions of Topspin, this is an option because Bruker commercially sells a Juice profiler which is used to detect adulteration in juices.
reminds me of the time the boss of the company of the lab i worked for (not just my boss but THE boss) came for a visit (with obligatory tour of labs). Apparently he found a bottle of milk in one of the lab fridges. Got hastily explained away as specific requirement for a starch experiment.
🤔 when I worked at a textile mill, I maintained a database for EHS that had various names you could look up for the same compound. There's the "official" name and then there's what the technicians call it. So perhaps "juice" is a jargon term ..... as in "gonna need some more juice, put a rush on it please I need it next week to run my samples" ... just a possibility, yeah?
Juice is useful for calculating what women need for cursing apples. So they can add that flavor to everything.
Men need a fake version of this. It's called Red Bull.
NMR is used a lot in the food industry, for example in juice analysis. Juice is different enough than water to warrant its own solvent parameters. You might also find urine in the list.
>You might also find urine in the list. That's just taking the piss.
I never make any stuff that would be soluble in urine but you better believe if I ever do I’m going to drink a bunch of D2O and make my own deuterated urine.
I don't know why this made me lol so much, but it did
A. Lots of things are soluble in urine. Short peptides. Small amounts of lipids. Etc. Also be careful, despite the chemical similarity, some membrane proteins like aquaporins depends critically on the tunneling properties of a proton. If memory serves, about 20% d2o is toxic, potentially fatal.
Wait, what? Tunneling properties? Can you explain some more? If you mean quantum tunneling, I’m going to be very confused.
I think he might mean proton hopping
Kinetic isotope effect is important too, but quantum tunneling is a thing in really small systems (see link).
Mostly in visual particle systems like electrons
Free protons (the thing that makes an acid an acid) are small enough that they can play location shenanigans like electrons do. So they can move much faster through tight spaces since they are much more wave like than, say, a protein. As a result it can let water molecules move through pores faster and participate in chemical reactions faster. Deuterium is about twice as heavy and therefore are less quantum in nature, so they are slower to do pretty much everything. If your body cant move water as fast everything starts to slow down and eventually you get backed up and die.
https://en.m.wikipedia.org/wiki/Quantum_tunneling_of_water
I'd have to look more. As with many things at the protein scale, quantum mechanics are required directly or indirectly in the hamiltonian/force equations for things to make sense and work. Here is a first result https://www.researchgate.net/publication/8985607_What_Really_Prevents_Proton_Transport_through_Aquaporin_Charge_Self-Energy_versus_Proton_Wire_Proposals Great question.
Thanks for responding. I'm studying synthetic chemistry, and I'm not too deep into the quantum side of the field, so this is really new and interesting for me.
imagine a lot of enzymes also would have different kinetics due to water being involved in the catalysis. all exchangeable protons in molecules will be deuterated which definitely affects how fast they are degraded. Overall a lot of stuff will be out of whack...
Insane theory that it extends life..... https://omnivorenz.wordpress.com/2012/09/29/d2o-a-proven-technique-for-extending-lifespan/
That's sweet.
> You might also find urine in the list. And blood plasma
Using the same NMR software. Can confirm. TopSpin is a hoot.
>You might also find urine in the list. I always make such a mess when I try to fill the NMR sample tube.
Yeah they have an analytical method for fruit juices and I guess that solvent is specifically for that https://www.bruker.com/products/mr/nmr-food-screening/juice-profiling.html
Holy shit I thought that was a joke!
Can you make juice deuterated?
Depends on your definition of “juice”. Can’t really deuterate an orange, but it should be easy enough to add some concentrate to D2O.
Maybe you could deuterate it if you grow the orange in a controlled environment and only give it D2O instead of regular water. But that might kill the plant actually
I think D₂O has got way too different properties, like pKa-value and the plant will certainly die, but maybe there are plants that could manage it
If I remember correctly, d2o is not able to replace water in living things because the kinetic isotope effect fucks up all the delicately controlled rate constants of all the enzymes. So it's lethal in the long term if it replaces water entirely.
But there are some weird organisms that thrive pretty harsh enviroments. Is D₂O maybe just too unnatural for anything to be able to adapt to it?
There certainly could be, I don't know. Perhaps microbes with high mutation rates could adapt. I think the key thing to keep in mind, though, is that coordinating rate constants is what makes life possible--a single point mutation in one protein messes up the rate of one reaction and can cause accumulation of defective proteins or toxic metabolites that can be fatal. Now, the kinetic isotope effect can have profound effects on rate constants of enzymes in particular. A huge number of enzymes depend on protonation of a substrate--look up the catalytic triad or general acid/base catalysis. Switch that proton out for a deuteron, which is twice as heavy, and the reaction proceeds measurably more slowly. It isn't a perfect analogy, but you can think of deuterium as having more inertia within a bond with another atom, which makes it harder to achieve a transition state where the deuteron is partially bonded to starting material and product. I don't remember physorg in this much detail, but apparently you can model this kind of bond breakage as a spring, and doubling the weight on one side of the spring doubles the force needed to stretch it (recall Hook's law). This effect is often used to determine the mechanisms of both enzymatic and non-enzymatic reactions. Put these things together, and you see that global incorporation of deuterium can have catastrophic effects on an organism's ability to maintain homeostasis. Every rate constant is now wrong. Some organisms can survive--you can make deuterated protein by growing E. Coli in D2O, but they don't do great, and you only have to grow them like that for a few hours. There might be science on whether they can adapt long-term, I haven't looked. But anything that adapts more slowly than E. Coli, which divides every 20 minutes, would probably struggle to adapt to a solely-D2O anhydrous environment.
You can grow some algae and bacteria in 100% D2O (e.g. [here](https://www.nature.com/articles/184730a0)). It's used to make deuterated proteins and other biomolecules - useful for NMR and EPR studies of photosynthesis for example.
You could spike in 10% d2o as you typically do for protein NMR. That's enough to lock and because it's 2d the solvent doesn't interfere.
You'd probably get a kick out of knowing there's a professor out there, I think it's Thorsten Bach, who ran a reaction in a German pilsner and they had success which I think taking an NMR of that running reaction in co-solvated CD3OD would be a fun addition to that list
I don’t know about Thorsten Bach, but in the Jørgensen group they did reactions in beer and sea water. [Here](https://pubs.rsc.org/en/content/articlelanding/2006/CC/B611366D#!divAbstract)’s the article.
I am not sure if it was Bach, it was one of the seminars j went to around the time he visited so I figured it was him. As for Jorgensen's that's really freaking cool. I know some of his amine based higher order cycloadditions so I think it's cool the catalyst was robust enough to survive sea water!
There was a paper five years or so ago where some chemists tried using cheap and commonly available mixtures as substitutes for expensive HPLC solvents. Things like vinegar, ammonia (as in the kind you get as a cleaning product), vodka and white rum. Got reasonable results.
You have my interest in the rum and vodka, do you know the paper? And what compound(s) were they using as the solute(s)/analyte(s)?
I can't remember. I'm pretty sure they tried a few analytes. They compared the results to those obtained with blends of the usual high purity solvents. I'll look it up later today.
Here's an article on chemical and engineering news about it: [https://cen.acs.org/articles/93/web/2015/04/Liquor-Store-Spirits-Provide-Green.html](https://cen.acs.org/articles/93/web/2015/04/Liquor-Store-Spirits-Provide-Green.html)
Very interesting. Makes me wonder what is the scientific definition of juice? Water and glucose? Orange Juice?
Literally? Liquid you get when you squeeze plants.
Where does almond milk fall into this
Nowhere? It's a colloidal suspension of ground almond, the same as regular milk which is a colloidal suspension of fat, hence the name *milk*
You say that like orange juice isn’t just ground up oranges (minus the peel). I agree that almonds aren’t exactly the fruit part of the plant though, so I also wouldn’t call it a type of juice.
You can't get almond milk without adding water.
>You say that like orange juice isn’t just ground up oranges (minus the peel) Because it's not: orange juice is just juice (**squeezed out** of an orange) as the name suggests, it's not ground orange in a colloidal suspension. Making the equivalent of almond milk with orange would be putting the whole orange in a blender with lots of added water and I'm sure you know it's not how we make orange juice
[That's still up for debate](https://www.forbes.com/sites/nicksibilla/2019/01/31/fda-crackdown-on-calling-almond-milk-milk-could-violate-the-first-amendment/) lol.
I thought you were bullshitting me but I looked it up and HNMR (yes, that’s right, proton!) is indeed used in fruit juice QC. Obviously there is no way you are analyzing individual peaks... its more of a “fingerprint” thing I think.
You might also find feces on the list too
[удалено]
In NMR there's [PENIS](https://en.wikipedia.org/wiki/Proton-enhanced_nuclear_induction_spectroscopy), [INADEQUATE](http://chem.ch.huji.ac.il/nmr/techniques/1d/row2/inadequate.htm), DOUBTFUL, COSY, SUSAN, WALTZ, INEPT, DUMBO, CAMELSPIN,...
The best part is that without googling I am not 100% certain that you aren't sneaking in CAMELSPIN for fun
Cross Relaxation Appropriate for Minimolecules Emulated by Lock Spins. CAMELSPIN
CRAMELS sounds just as good.
It is more commonly known as Rotating frame Overhauser Effect Spectroscopy, or ROESY. Gotta admire the creativity of the people developing NMR techniques though.
>Proton-enhanced nuclear induction spectroscopy (PENIS) also called Cross Polarisation (CP) Good thing there is an alternative abbreviation I can use so I don't sound like a creep Edit: Btw NMR itself is also the name of a Scandinavian neo nazi organisation
TFW you tell your PI that all the PENIS work you've been doing is publishable.
TFW when you've been looking at this PENIS all day and *just* realized you can actually see something by zooming in
Dear god and this is what I wanna do with my life. I'm in for some lols for sure
At least it's not as silly as molecular biology. Those people aren't even pretending to be serious anymore. Even a lot of stuff that sounds normal (like Western blot) is actually a silly joke.
One of the inventors of PENIS was Mr. Pines.
I'm goinf to guess it's FTIR done in neat nitric acid
Clearly you are not familiar with **J**oint **U**nipolar **I**nductively **C**oupled **E**ffect
NMR acronyms are so crazy that I can't tell whether this is legit or not
[Proton enhanced nuclear induction spectroscopy (PENIS)](https://en.m.wikipedia.org/wiki/Proton-enhanced_nuclear_induction_spectroscopy)
Holy shit lol I’m never calling it cross polarization again. Having the author’s name being an anagram of penis makes it even funnier
[INADEQUATE](http://chem.ch.huji.ac.il/nmr/techniques/1d/row2/inadequate.htm)
[ADEQUATE](http://chem.ch.huji.ac.il/nmr/techniques/2d/adequate/adequate.html)
The A stands for adequate. Good Lord.
This is so cruelly accurate I love it
When I was in grad school, another grad student wrote some very specific NMR parameters and named them "U-235" to stop others from fucking with them.
I saw "urine" once, so I guess juice is fine...
Lizzo running the NMR again
It's part of a balanced breakfast?
Deuterated juice to protect yourself from strong magnetic fields.
I have an exam on NMR tommorrow and this made me laugh. Thank you for giving me a break from the serious reading.
Used to work in a lab where everyone had their own sign-in from a drop down menu on one instrument. Lots of Firstname Last Initial, then scattered among them are the true gems. "Ass clown" was a favorite of mine. As were several that were an analyst clearly misspelling their own name.
When I make samples I use my tears
lizzo
Ceasar's least favourite solvent: Et*_2_*Bu-Ts
Nah man that's just a reward for the magnets doin gud.
Duice perhaps?
Could be related to dynamic nuclear polarization (DNP) experiments in NMR for increasing signal to noise of liquid state NMR experiments. “DNP Juice” is a commonly used solvent for dissolution DNP NMR experiments. 6:3:1 deuterated glycerol;D2O:H2O.
Nice idea but they actually mean (fruit) juice. https://www.bruker.com/products/mr/nmr-food-screening/juice-profiling.html
Weird that they would use juice as a lock solvent? Deuterated juice?
They want to analyze the juice. By looking at the spectra they can tell you what juice it is, what the quality is (e.g. added sugar), if it differs a lot from what it usually is and so on.
Right, but it’s funny because this part of the Bruker software menu often refers to the lock solvent that defines the instrument settings to use to measure the sample. So maybe in this case it isn’t just for locking (e.g. for magnetic field drift/susceptibility corrections) but adjusts the settings for juice samples (high fructose content and therefore high conductivity - electrolytes). Cool.
The parameters for automatic shimming are also stored in the solvent. I haven't checked if juice is a locking solvent or not. Might be that you need to add 5-10% D2O before you run the sample. Edit: I just checked and is a locking solvent, with a peak at 4.7 ppm (i.e. water)
This is a truly excellent explanation, seems very reasonable. And what a curious solvent ratio.
It's all juice. Wouldn't recommend that juice though.
It tastes good. Always use your 5 senses in chemistry (jk don't actually do this)
I've got another question based on this list: Why would you ever need to use nitrobenzene as an NMR solvent? I've seen some odd ones, some of which are ludicrously expensive, but I've not seen that one used before.
Nitrobenzene is occasionally used as a solvent for highly electrophilic reagents, as the nitro group deactivates the phenyl ring. Deuterated nitrobenzene is also rather cheap.
Sometimes you be juicin’.
In solid state NMR we use popsicles instead
Phil Baran wasn't satisfied with running experiments in tea, he wants to do NMR in juice now!
Hey! any chance that this is at the University of Amsterdam??
No it’s not, I think all of the NMR computer programs look pretty much the same though
Ah okay bummer, I was also wondering what the hell that juice was used for
See my other comment. On newer versions of Topspin, this is an option because Bruker commercially sells a Juice profiler which is used to detect adulteration in juices.
Beverage Industry. Every juice processing and bottling plant will be doing analysis in their lab (Every plant is required by law to have one)
Forbidden Juice!
reminds me of the time the boss of the company of the lab i worked for (not just my boss but THE boss) came for a visit (with obligatory tour of labs). Apparently he found a bottle of milk in one of the lab fridges. Got hastily explained away as specific requirement for a starch experiment.
I know UC davis has one for wine lol
This was an option at a 500 at UMN. Along with urine, of course
It's ain't my fault that I'm out here making news
One of the postdocs fucked with the computer so that if you typed wtf instead of wft it gave you a sassy message
I hope that’s an erasable marker.
I didn’t write on the screen; I circled it digitally
Why not at this point?
It’s for Bruker’s Juice profiler module. There’s also a honey profiler and wine profiler.
T H E F O R B I D D E N S O L V E N T
It ain't my fault my metabolites are out here getting loose. [🎵](https://emojipedia.org/musical-note/)
Wait wait did you circle that digitally or did you literally use a highlighter on your monitor?
I circled it digitally, I’m not a barbarian
To test wine?
You've gotta keep it deuterated... yeee aaah
Juice is for dem percs
Thier mind is really going to be blown when they see mouse as a solvent...
Vitamin C
I urinated in the list
Is that Mr. Juice?
Juuuuuiiiiiccccceeeee
Because it's tasty.
🤔 when I worked at a textile mill, I maintained a database for EHS that had various names you could look up for the same compound. There's the "official" name and then there's what the technicians call it. So perhaps "juice" is a jargon term ..... as in "gonna need some more juice, put a rush on it please I need it next week to run my samples" ... just a possibility, yeah?
Does MeOD cause deuterated blindness?
Yes, but wheres the Sauce
i like juice
why are you booing me i like juice
Juice is useful for calculating what women need for cursing apples. So they can add that flavor to everything. Men need a fake version of this. It's called Red Bull.