Chirality

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Markbnj

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I think I remember reading some years back that scientists were working on a "flipped" sugar molecule that would taste just like the sugar we use, but because of its "flippedness" would not have any calories (or energy, I assume). Don't know what became of it.
 

uclaLabrat

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Aug 2, 2007
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I think I remember reading some years back that scientists were working on a "flipped" sugar molecule that would taste just like the sugar we use, but because of its "flippedness" would not have any calories (or energy, I assume). Don't know what became of it.
Probably didn't work too well, taste receptors are also chiral, like most receptors in the body, and they tend to form matched or mismatched pairs.

carvone is one example...one enantiomer smells like spearmint, the other smells like caraway seeds.
 

destrekor

Lifer
Nov 18, 2005
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Probably didn't work too well, taste receptors are also chiral, like most receptors in the body, and they tend to form matched or mismatched pairs.

carvone is one example...one enantiomer smells like spearmint, the other smells like caraway seeds.

They have produced L-glucose and it tasted equally as sweet as D-glucose but did not result in any activity related to glucose consumption, in that it wasn't metabolized nor impact insulin. It also acted as a laxative, which seems to be a common theme with undigested sugar-replacements like the various sugar alcohols.

I guess a big problem with L-glucose is that it is entirely an artificial production and had a high price tag. There is no natural source of L-glucose.

I think a similar version of Lactose was produced, not sure if it is on the market, I don't care to look right now.
 

uclaLabrat

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They have produced L-glucose and it tasted equally as sweet as D-glucose but did not result in any activity related to glucose consumption, in that it wasn't metabolized nor impact insulin. It also acted as a laxative, which seems to be a common theme with undigested sugar-replacements like the various sugar alcohols.

I guess a big problem with L-glucose is that it is entirely an artificial production and had a high price tag. There is no natural source of L-glucose.

I think a similar version of Lactose was produced, not sure if it is on the market, I don't care to look right now.

I think I knew that, but my bad. Thanks for the reminder.
 

EliteRetard

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Mar 6, 2006
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Wasn't it something like spearmint and caraway are exactly the same molecularly? Just one is "left" and the other "right".

Reminds me of a joke my dad used to tell about the dudes building a house. The new guy kept throwing away nails and foreman came over and was like WTF?! The new guys was like "they are facing the wrong way." The foreman was like "those are for the other side of the house!"

Now obviously I don't tell it as good as he did...but you get the idea.
 

OverVolt

Lifer
Aug 31, 2002
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Right handed DNA encodes left handed proteins that work on right handed substrates. Derp.

I think I was saying in another thread that symmetry in biological molecules is responsible for their formation. Which is why life exists, because collections of symmetric molecules are favored by entropy despite the increased order.

There are bilaterally symmetric lifeforms and radially symmetric lifeforms. Except sponges, go home sponges you're drunk.
 
Last edited:
Dec 10, 2005
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Right handed DNA encodes left handed proteins that work on right handed substrates. Derp.

I think I was saying in another thread that symmetry in biological molecules is responsible for their formation. Which is why life exists, because collections of symmetric molecules are favored by entropy despite the increased order.

There are bilaterally symmetric lifeforms and radially symmetric lifeforms. Except sponges, go home sponges you're drunk.

Derp sounds about right.

Some biological molecules are symmetric, but many are not. Proteins pretty much lack symmetry (you might see some 2-fold or 4-fold rotational symmetry in a quaternary complex though, like hemoglobin). DNA is not symmetric. Sugars are not symmetric. Hell, even the cell membrane is asymmetric - different lipids and proteins face the inside versus the outside.

Entropy would favor more disorder, not more order. But overall, that's hard to measure, because you have many sources of entropy to consider: side chain entropy (how many conformations does an amino acid side chain have), conformational entropy of the protein, solvent entropy, etc... There is also the enthalpy, where if it is low enough, you can easily overcome the entropy barrier and have a molecule sitting in a thermally stable state.
 

Bob the Coder

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Whereas I, steeped in the quotidian ignorance of the great unwashed, did not.

But now, I, thanks to my life long quest to better myself intellectually and my opposable thumb, was able to operate my Marconi such that I now stand with you in the glorious light of higher awareness.

<-------- Looks at Mixo's brunch plate.

You gonna' finish that? :awe:

Jesus Christ who talks like this? Do you practice in front of a mirror?
 

OverVolt

Lifer
Aug 31, 2002
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Derp sounds about right.

Some biological molecules are symmetric, but many are not. Proteins pretty much lack symmetry (you might see some 2-fold or 4-fold rotational symmetry in a quaternary complex though, like hemoglobin). DNA is not symmetric. Sugars are not symmetric. Hell, even the cell membrane is asymmetric - different lipids and proteins face the inside versus the outside.

Entropy would favor more disorder, not more order. But overall, that's hard to measure, because you have many sources of entropy to consider: side chain entropy (how many conformations does an amino acid side chain have), conformational entropy of the protein, solvent entropy, etc... There is also the enthalpy, where if it is low enough, you can easily overcome the entropy barrier and have a molecule sitting in a thermally stable state.

Nope nope nope.


This is how your body stores D-glucose as glycogen for starters. It is also in a staggered compact arrangement per the golden ratio. The symmetric pattern is due to the handedness of glucose.

http://www.maths.surrey.ac.uk/hosted-sites/R.Knott/Fibonacci/fibnat.html

These patterns repeat through nature on both the molecular and cellular level. (Specifically referencing nautilus shells and seed heads)

Also the bilayer is symmetrical ya dolt At low concentrations of lipids, you get micelles, and at high concentrations, you get bi-layers. Always. Ordered arrangement favored by symmetry. Bam. Lab repeatable. This is basic stuff.

And those proteins in the bi-layer? All of them are beta-barrels. The hydrophobic sections of those proteins have you guessed it, symmetry.

http://www.mdpi.com/2073-8994/4/1/15

And DNA:

http://link.springer.com/chapter/10.1007/978-1-4684-3417-0_5

I'm so sorry for your loss. Symmetry plays a large role not only in the bases but also in the structure of DNA.

So I guess as an example dyad symmetry is responsible for the formation of hairpin loops.

https://books.google.com/books?id=m...wCw#v=onepage&q=double helix symmetry&f=false

There is so much symmetry in DNA its absurd.
 
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Gibsons

Lifer
Aug 14, 2001
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Nope nope nope.


This is how your body stores D-glucose as glycogen for starters. It is also in a staggered compact arrangement per the golden ratio. The symmetric pattern is due to the handedness of glucose.

http://www.maths.surrey.ac.uk/hosted-sites/R.Knott/Fibonacci/fibnat.html
I'm not so sure how accurately 2d cartoon represents 3d reality, but whatever.

These patterns repeat through nature on both the molecular and cellular level. (Specifically referencing nautilus shells and seed heads)

Also the bilayer is symmetrical ya dolt At low concentrations of lipids, you get micelles, and at high concentrations, you get bi-layers. Always. Ordered arrangement favored by symmetry. Bam. Lab repeatable. This is basic stuff.
So any two chain phospholipid can make micelles?
And those proteins in the bi-layer? All of them are beta-barrels. The hydrophobic sections of those proteins have you guessed it, symmetry.

I don't think you should call someone a dolt, then proceed to make such a gaffe.
 
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