Homochirality: Why Nature Never Makes Mirror Molecules

Summary

This video script delves into the concept of chirality, explaining why sugar solutions twist polarized light to the right due to the chiral nature of sugar molecules. It explores why all commercially available sugar is right-handed, which is linked to the homochirality observed in nature where all chiral molecules, like sugars, amino acids, and DNA, exhibit only one handedness. The script also discusses the challenges and importance of creating homochiral molecules in industries like pharmaceuticals, where different enantiomers of a drug can have vastly different effects. Furthermore, it touches on the fascinating idea of chirality in subatomic particles, like quarks, and their interaction with the weak nuclear force.

Takeaways

• 🍬 Sugar molecules are chiral, meaning they lack mirror symmetry and can twist polarized light to the right.
• 👐 The term 'handedness' is used to describe the non-superimposable mirror image property of chiral molecules, similar to our hands.
• 🛒 Commercial sugar is composed of right-handed molecules, which is the same type produced by plants.
• 🌿 Plants produce right-handed sugar using enzymes, which are chiral proteins that catalyze the formation of sugar molecules one at a time.
• 🔬 The concept of 'Homochirality' explains why all molecules of the same type in nature share the same handedness, such as all sugars being right-handed and all amino acids being left-handed.
• ⚙️ The reason behind the uniform handedness in enzymes could be due to the efficiency and interoperability of biological systems.
• 🤝 Just as shaking hands with the wrong hand would be inefficient, having a mix of left and right-handed molecules would disrupt biological processes.
• 🌌 The origins of homochirality in life could be due to a random event that led to a self-replicating molecule of one handedness dominating the early Earth.
• 🔬 The 'RNA world hypothesis' suggests that early life was based on RNA, which can replicate and store information, but requires a homochiral environment to function.
• 💊 The pharmaceutical industry emphasizes the importance of homochiral molecules, as different enantiomers of a drug can have vastly different effects on the body.
• 🚀 The search for extraterrestrial life includes studying chirality, as evidenced by the experiment sending both enantiomers of sugar to Mars to test for metabolism by potential life.

Q & A

Why does a sugar solution twist polarized light to the right?

A sugar solution twists polarized light to the right because sugar molecules are chiral, meaning they lack mirror symmetry. This property causes them to interact with light in a way that results in the twisting effect.

What is meant by the term 'chiral' in the context of sugar molecules?

Chiral refers to the property of an object that cannot be superimposed onto its mirror image. In the context of sugar molecules, it means that the molecular structure is not symmetrical and does not have a mirror image counterpart.

What is the difference between a left-handed and right-handed sugar molecule?

A left-handed sugar molecule is the mirror image of a right-handed sugar molecule. They are different in the way they twist light; right-handed sugar molecules twist polarized light to the right, while left-handed ones would theoretically twist it to the left.

Why are all sugar molecules obtained from shops right-handed?

All sugar molecules obtained from shops are right-handed because plants, which are the natural source of sugar, always produce right-handed sugar molecules. This is due to the enzymes involved in sugar production within the plant, which have the same handedness and thus produce sugar with the same handedness.

What is the term used for the opposite handedness versions of chiral molecules?

The term used for the opposite handedness versions of chiral molecules is 'enantiomers'.

What is 'Homochirality' and why is it significant in nature?

Homochirality is the phenomenon where all the chiral molecules found in nature have only one of the two possible handednesses. It is significant because it ensures the interoperability and efficiency of biological systems, as having both handednesses would lead to inefficiencies and failures in biological processes.

How do enzymes contribute to the production of homochiral sugar molecules in plants?

Enzymes, which are chiral proteins, contribute to the production of homochiral sugar molecules by bringing together ingredients and catalyzing the formation of sugar molecules. Since all the enzymes involved in sugar production have the same handedness, they produce sugar molecules with the same handedness.

What is the 'RNA world hypothesis' and how does it relate to the homochirality of life?

The 'RNA world hypothesis' suggests that the first self-replicating molecules of life were RNA-based. This is relevant to homochirality because RNA can only be formed and replicated efficiently if all the nucleotide bases have the same handedness, which supports the idea that life chose one handedness over the other.

Why is it difficult to create homochiral molecules in a lab or factory?

Creating homochiral molecules is difficult because chemical reactions typically result in a 50/50 mix of both enantiomers. Separating these enantiomers is challenging due to their nearly identical chemical properties, requiring specialized techniques such as using homochiral enzymes to selectively remove one enantiomer.

What are some examples of how different enantiomers of a drug can have different effects on the body?

Different enantiomers of a drug can have drastically different effects. For example, one enantiomer of ibuprofen is effective as a pain reliever, while the other is inactive. Thalidomide is another example, where one enantiomer helps with morning sickness, while the other causes birth defects.

How is the concept of chirality relevant to the search for extraterrestrial life?

Chirality is relevant to the search for extraterrestrial life because if life on another planet were similar to life on Earth, it would likely have the same homochiral properties. This concept was considered in missions to Mars, where both left- and right-handed sugars were sent to test for life that could metabolize them.

Outlines

00:00

🍬 The Chirality of Sugar Molecules

This paragraph discusses the chirality of sugar molecules and why they twist polarized light. It explains that sugar molecules are chiral, meaning they lack mirror symmetry, similar to hands. All sugar molecules found in stores are right-handed due to the enzymes in plants that produce them, which also have the same handedness. The concept of enantiomers is introduced, and the video touches on the idea of homochirality in nature, where all chiral molecules of a certain type share the same handedness.

05:03

🌿 Homochirality in Nature and Efficiency

The speaker elaborates on the concept of homochirality, where all chiral molecules in nature, such as sugars and amino acids, are found in only one handedness. This uniformity is crucial for efficiency and interoperability in biological systems. The paragraph uses the analogy of handshaking to illustrate the inefficiency of a mixed-handed world. It also touches on the interconnectedness of life and the hypothetical scenario of a mirror-image universe to emphasize the importance of homochirality.

10:10

🔬 The Origin of Homochirality and the RNA World Hypothesis

This section delves into the origins of homochirality, presenting two hypotheses: one where a self-replicating molecule happened to form with a specific handedness, leading to a predominance of that handedness in the world, and another where multiple replicating systems with different handednesses competed, with one eventually taking over. The paragraph also discusses the 'RNA world hypothesis,' which suggests that early life was based on RNA molecules that could only replicate with a single-handedness, thus necessitating a homochiral environment.

15:10

🛠️ Creating Homochiral Molecules and Their Importance

The speaker talks about the difficulty and importance of creating homochiral molecules, especially in the pharmaceutical industry, where different enantiomers of a drug can have vastly different effects. The paragraph explains the process of using enzymes to filter out unwanted enantiomers and highlights examples of drugs where only one enantiomer is active or where different enantiomers have drastically different effects. It also mentions the historical attempt to detect life on Mars by sending both mirror images of sugar.

🧠 Chirality in Subatomic Particles and Learning Resources

The final paragraph introduces the mind-bending concept of chirality in subatomic particles, such as quarks, which are treated differently by the weak nuclear force based on their handedness. The speaker then transitions to promoting online learning through Skillshare, sharing a sponsored link and a list of diverse courses that could be beneficial for viewers, ranging from exam study techniques to storytelling and productivity.

Keywords

💡Sugar

Sugar is a class of organic compounds characterized by a sweet taste and used as a nutritional source by living organisms. In the video, sugar is highlighted for its chiral nature, meaning it can exist in two forms that are mirror images of each other. The script discusses how sugar molecules in nature are predominantly right-handed, which is a key point in understanding the concept of homochirality in biology.

💡Chiral

Chirality is a property of asymmetry important in several branches of science. The term 'chiral' is used in the script to describe molecules, such as sugar, that cannot be superimposed on their mirror image. This concept is central to the video's theme, as it explains why all sugar molecules from shops are right-handed and the implications of this chirality in nature and industry.

💡Enantiomers

Enantiomers are one of two stereoisomers that are mirror images of each other but are not identical, much like left and right hands. The script uses the term to describe the left and right-handed versions of sugar molecules, emphasizing that in nature, we predominantly find one enantiomer of sugar, which is the right-handed version.

💡Handedness

Handedness refers to the property of an object being non-superimposable on its mirror image. In the context of the video, handedness is used to describe the direction in which sugar molecules twist polarized light and how this relates to the molecules being either left or right-handed, as well as the broader concept of homochirality.

💡Homochirality

Homochirality is the phenomenon where an excess of one enantiomer over the other exists in a biological or chemical system. The video explains homochirality by pointing out that all sugars are right-handed and all amino acids are left-handed in nature, which is crucial for the efficiency and interoperability of biological systems.

💡Enzymes

Enzymes are large proteins that act as biological catalysts, speeding up chemical reactions in living organisms. The script explains that enzymes, which are chiral themselves, are responsible for the production of chiral molecules like sugars, and their handedness determines the handedness of the molecules they produce.

💡RNA World Hypothesis

The RNA world hypothesis proposes that early life was based on RNA, which could both store genetic information and catalyze chemical reactions. The video discusses this hypothesis in the context of understanding how homochirality could have arisen, given that RNA replication requires a uniform handedness of nucleotides.

💡Pharmaceutical Industry

The pharmaceutical industry is involved in the research, development, and marketing of drugs for medical use. The script mentions the industry in relation to the importance of homochirality, as different enantiomers of a drug can have drastically different effects, with some being therapeutic and others harmful.

💡Quarks

Quarks are elementary particles and a fundamental constituent of matter. The video introduces the concept of chirality at the subatomic level by mentioning that quarks, which are considered point-like particles, come in left and right-handed versions, and only left-handed quarks interact with the weak nuclear force.

💡Skillshare

Skillshare is an online learning community with thousands of classes in design, business, technology, and more. In the video, the creator promotes Skillshare as a sponsor, offering a link for viewers to try the platform for free, which is an example of how educational content can be supported and disseminated.

Highlights

Sugar molecules are chiral, lacking mirror symmetry like a left hand does not mirror into a right hand in a reflection.

Commercial sugar consists of right-handed molecules that twist polarized light to the right.

Chirality in molecules is formally referred to as having left and right enantiomers.

Glucose sold in shops is always the right-hand enantiomer.

Plants produce sugar molecule by molecule using enzymes, which are also chiral.

Enzymes involved in sugar production have the same handedness, leading to uniform sugar molecules.

Homochirality is a natural phenomenon where all chiral molecules have the same handedness.

Interoperability and efficiency drive the prevalence of one handedness in biological systems.

Hypothetical scenarios suggest that a mirror universe would be incompatible with life as we know it.

The origin of homochirality in life could be attributed to chance or a non-50/50 mix in the primordial soup.

The RNA world hypothesis suggests RNA-based replicating molecules that could only function with a single chirality.

Creating homochiral molecules is challenging and important in various industries, including pharmaceuticals.

Different enantiomers of drugs can have vastly different effects, with some being harmful.

The search for extraterrestrial life involves the study of chirality, such as sending both mirror images of sugar to Mars.

Chirality extends to subatomic particles like quarks, which have left and right versions and different interactions with forces.

Skillshare offers a variety of courses that can enhance various skills, from exam studying to storytelling.

Transcripts

- I made a video a couple of weeks ago

explaining why a solution of sugar will always twist

polarized light to the right.

I recommend you watch the original video

if you haven't already, but if you don't want to

then the short answer is because sugar molecules are chiral.

I didn't actually use the word, "Chiral,"

in the original video, which is a shame

'cause it's a good word.

I talked about handedness instead,

which basically means the same thing.

It just means that the molecule of sugar

doesn't have mirror symmetry in the same way

that my left hand doesn't have mirror symmetry.

If you look at my left hand in the mirror

you won't see another left hand, you'll see a right hand.

It's the same thing with sugars.

If you buy sugar from the shops,

then all those sugar molecules in there

will be right-handed.

They will all turn light to the right.

To use the formal language, all chiral molecules

have a left-hand version and a right-hand version.

They're called the enantiomers of the molecules.

So look, here's one enantiomer of glucose

and there in the mirror, that's the other enantiomer.

And when you buy glucose from the shops,

it's always, always, always the right-hand enantiomer

that you get.

(enantiomer clicking)

Now, many of you were not entirely satisfied

with my explanation and quite rightly

because there's a big question mark.

Why are all the sugar molecules

that you buy from the shops right-handed?

And it's a good question

because if you were to make some sugar for yourself

in a chemistry lab and mixing some chemicals together,

you would get a 50/50 mix of left-handed sugar

and right-handed sugar.

But we don't make sugar in the lab.

We get sugar from plants

and plants always make right-handed sugar.

So now you should be satisfied.

"But wait.

"Why do plants always make right-handed sugar?

"You haven't given us a full explanation at all!"

Well, plants don't make sugar by mixing chemicals together,

like we would do in a lab.

Instead a plant make sugar one molecule at a time,

using tiny molecular machines.

When I say tiny molecular machines,

I'm talking about enzymes.

These large proteins that bring the ingredients together

and stick them together.

And these proteins are chiral themselves.

There's a left-hand version and a right-hand version,

but you only ever see one of those enantiomers.

So if all the enzymes that are involved

in the production of sugar all have the same handedness,

then they will produce sugar molecules

that all have the same handedness.

And so now you should be satisfied.

"But wait, hold on a second.

"Why do all the enzymes have the same handedness?

"That doesn't make sense?

"You need to explain that as well!"

All right.

So there's this thing in nature called, "Homochirality."

All the molecules found in nature, or at least

all the chiral ones, are only ever found

with one of the two possible handednesses.

So for example, all sugar is right-handed.

All amino acids are left-handed.

DNA is always right-handed.

Any kind of molecule that's chiral,

you only ever find one of the enantiomers

and never the other.

And that needs to be explained.

Homochirality pops up in lots of different places,

by the way, not just biology.

For example, screws are homochiral.

The vast, vast majority of screws that you can buy

are right-handed screws.

And that's a good thing.

Imagine if manufacturers produced

sometimes left-handed, sometimes right-handed,

the phrase, "Righty tighty, lefty loosey,"

would only apply 50% of the time.

Fusilli pasta is mostly homochiral.

Though I did find one brand that does it the other way.

Scissors are chiral. (scissors snipping)

Yeah, they're designed for right-handed use.

Look, as I'm

cutting the page here (scissors cutting)

I can see where the blade (scissors cutting)

is cutting through the paper. (scissors cutting)

But if I try and do that with my left hand

the blade is obscuring the location of the cut.

I'm left-handed actually and I once went to a shop years ago

in central London that sells things for left-handed people,

anythinglefthanded.co.uk.

And I tried out the left-handed scissors.

I couldn't get used to it because I'd spent my whole life

learning to use right-handed scissors with my right hand.

How sad is that?

Imagine if growing up I had access to left-handed scissors?

I'd be cutting away like anything.

It'd be amazing.

I'd be this grand cutter of things.

As it is I'm a suboptimal cutter of things

with my non-dominant hand.

- [Director] Get on with it.\!

- Yeah, all right.

So we need to explain why all the molecules in nature

are only ever found in one of the possible

mirror image options and not the other.

It's all to do with interoperability and efficiency.

Like, imagine if there were two versions of everything.

Like, if there were both versions of the sugar,

then the enzymes that we use to metabolize sugar

and get the energy from it,

you would need both versions of those as well.

And if you did.

If you had both left and right versions of sugar

and left and right versions of the enzymes

that we use to metabolize sugar, then...

Even if you had that system like half the time,

you'd have the wrong kind of sugar

bumping into the wrong kind of enzyme.

So it would be hugely inefficient.

It's like, if we didn't agree to shake hands

with our right hand,

occasionally you'd go to shake hands with someone

and it would fail because you're shaking

with your left hand, they're shaking with their right hand.

You might not be wondering why you don't have

some life forms that do it all one way

and other life forms that do it all the other way.

But in reality, life is so interlinked.

You know, this species is gonna be linked to this species

through mutualism, or predation.

You know, then this species's gonna be linked

to this species.

The whole of biology is linked

in this massive web of things eating other things.

So you can't sustain a pocket of mirror image

because it will fail.

It won't be able to cooperate

with the rest of the biological system.

One fanciful consequence is that,

if through some weird space-time anomaly

you found yourself in a mirror version of this universe,

you would be absolutely screwed.

So

there's the answer.

Well, not quite because you might now ask,

"Well, why is it that way and not the other way?

"There's two options.

"Why did life choose this option?

"Why is it right-handed sugar, left-handed amino acids,

"right-handed DNA?

"Why isn't it left-handed sugars, right-handed amino acids,

"left-handed DNA?"

You can reframe the question by talking about

the primordial soup.

The conditions on Earth just before life emerged.

Scientists think that it was a mixture of simple molecules,

like sugars, amino acids, nuclear bases.

Those are all things that can occur naturally.

You don't need life to get those building blocks for life.

It's reasonable to assume that the primordial soup

was a 50/50 mix of left-handed and right-handed molecules.

So why was one set chosen over the other for life?

One hypothesis is that you've got these simple molecules

bumping into each other, randomly forming larger molecules.

And just by chance, at some point,

they bumped into each other in such a way

as to create a larger molecule that is self-replicating.

It's a rare event, so it only happens that one time.

And just by chance it happens with right-handed nucleotides

instead of left-handed nucleotides.

And so you've got this replicating molecule.

You're getting more and more of it.

It's evolving as well,

so it's getting even better at replicating,

creating more and more of itself.

So the population of right-handed nucleotides

and the corresponding right-handed sugars

and left-handed amino acids

are increasing in number in the world.

Eventually the world becomes full of homochiral molecules

and all those original molecules of the other handedness

decay away without being replaced.

Another possibility is that the emergence

of self-replicating molecules is not that rare.

And it happened more than once.

So you have this 50/50 mix of replicating systems.

One has one handedness, the other has the other handedness.

But that 50/50 mix is an unstable equilibrium.

If one of the populations grows slightly

compared to the other just by chance,

then it has an advantage because it's surrounded

by more of those molecules that it finds useful.

So the unstable equilibrium of a 50/50 mix

quickly moves away to a homochiral population.

The problem with both of those hypotheses

is that they don't fit well with the chemistry

that most scientists assume was driving life at the time.

It's called the, "RNA world hypothesis."

And it assumes that the initial

replicating molecules of life were RNA-based.

And it makes sense because RNA, which remember,

is the single-strand version of DNA.

It can be created spontaneously through

polymerization of a nuclear bases.

That can happen without the presence of life.

It can act as a store of information just like DNA can.

But unlike DNA it can also act as

the replicating machinery of life.

I didn't know this, but the ribosome,

you know, that big molecule inside your cells

that reads genetic code and spits out proteins

built from amino acids.

That molecule itself is not a protein built

from amino acids.

It's actually a tangled up RNA molecule.

In other words, you can have a system

of molecular replication that is just RNA-based.

The problem is this.

We know experimentally that if you try to grow RNA chains

by polymerizing nuclear bases,

you'll do fine, so long as all the nuclear bases

have the same handedness.

If you introduce the opposite handedness base,

it will shut down the process.

You can't grow RNA chains in a 50/50 mix of nuclear bases.

So either there's a system of molecular replication

that predates the RNA world model

and that system was able to create

the homochiral environment needed

for the RNA world to thrive,

Or there's somehow not a 50/50 mix

of left and right-handed molecules in the primordial soup.

And that needs to have arisen through non-biological means.

There are hypotheses that support both those options.

For example, there are chemical reactions

that are self-catalyzing.

So if you have a 50/50 mix of chiral molecules,

but one is slightly larger than the other,

so long as those chiral molecules are self-catalyzing,

as in, they create more of themselves as catalysts,

then you'll very quickly get to a homochiral mix.

We've never seen experiments of that happening

with the basic building blocks of life.

So there's still work to be done there.

Another option is that a bias for one handed molecule

over the other in the primordial soup came from space.

Some scientists have looked at the amino acids

found inside meteorites.

And if they found a bias for one handedness over the other,

it's always been for left-handed amino acids,

like we see here on Earth.

It could be that those meteorites are contaminated,

so more work needs to be done there as well.

It also pushes the question back.

Like, why would you find a non-50/50 mix of amino acids

on a meteorite?

In other words, we're getting to the point now where

no one knows for sure.

And while that doesn't work particularly well

for a YouTube video, it's good for science.

That's where the interesting stuff happens.

I'm gonna go on a slight tangent now.

Making homochiral molecules in a lab, or in a factory

is really difficult,

but it's also sometimes really important.

The reason it's difficult is because, normally

when you mix chemicals together, you're gonna end up

with a 50/50 mix of the chiral product.

So you then have to filter out the ones you don't want.

It's difficult to filter out the chemicals

because they're identical in almost every way.

So maybe you could use an enzyme.

So you use an enzyme to pluck out the mirror image

that you don't want.

Leaving you with the one that you do want.

And of course the enzyme needs to be homochiral as well,

otherwise it will pluck out the one you don't want.

Where'd you get this enzyme from?

Well, you steal it from nature.

So you find an organism that makes the enzyme that you want,

you figure out the bit of DNA that codes for that enzyme.

You stick that DNA in a bacteria,

you grow the bacteria, the bacteria makes the enzyme

and then you filter out the enzyme

and you use it to pluck out the mirror image

that you don't want.

Leaving you with the mirror image that you do want.

(sighing) That is one way to do it.

One area where it's important

to be able to make homochiral molecules

is in the pharmaceutical industry

because the mirror images of a drug

can have completely different effects.

Drugs tend to interact with receptors in the body.

And this simplified schematic of a molecule and a receptor

shows why one enantiomer of a molecule could line up

with the receptor while its mirror image

wouldn't be able to.

One harmless example is ibuprofen.

When you buy ibuprofen it's a 50/50 mix

of the two mirror images,

but only one of them does anything.

The other's completely useless.

The infamous example is thalidomide.

One mirror image helps with morning sickness,

the other mirror image causes birth defects.

And sadly, if you give someone a dose of just

the morning sickness mirror image

it actually becomes a 50/50 mix in the body.

Some other examples that I found.

One an enantiomer of ethambutol

is used to treat tuberculosis,

whereas the other mirror image causes blindness.

Levomethorphan is an opioid, whereas its mirror image

is an hallucinogenic cough medicine.

And the mirror image of meth is sold

as a nasal decongestant spray.

So my Google search history now includes the phrase,

"Meth nasal spray,"

Even sugar has an interesting history

of commercial synthesis.

So the left-hand version of sugar.

It still stimulates the sweetness receptors in the mouth,

which is obviously not sensitive to chirality

for whatever reason.

But it can't be metabolized in the body.

So it would be an amazing artificial sweetener

except that it's incredibly expensive to make.

By the way, the synthesis of left-handed sugars

is intimately linked to our search

for extraterrestrial life on Mars.

We sent a lander there with some sugar.

The idea being that if there was life on Mars

and it was like life on Earth,

then it would metabolize that sugar

and we'd be able to see the products of that metabolism.

But because we couldn't be sure that life on Mars

had the same handedness as life on Earth,

we had to send both mirror images of sugar.

We had to make the left-handed version of sugar.

One last thing that's absolutely mind-bending.

When you think about chiral objects,

they have physical extent, right?

Like, this is a three-dimensional object.

A two-dimensional object wouldn't be chiral in 3D space.

And it would be hard to imagine

subatomic particles being chiral.

And yet many of them are.

For example quarks come in left-hand

and right-hand versions.

These particles that we consider to be point-like.

In other words, zero-dimensional objects

moving around in three-dimensional space.

How can they possibly be chiral?

And even stranger, the universe treats them differently.

Only left-handed quarks feel the weak nuclear force.

In other words, the universe has a left-handed bias.

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