A-level course · Lesson 11 of 12

Chirality and the origin of life

Life uses left-handed amino acids almost exclusively. Some meteorites contain a small excess of left-handed forms, a clue to how this preference may have begun.

In this lesson you will
  • Identify chiral centres and explain optical isomerism.
  • Calculate an enantiomeric excess.
  • Evaluate evidence that meteoritic amino acid excesses are not contamination.

Links to: A-level chemistry, organic chemistry: optical isomerism, chiral centres, enantiomers, racemic mixtures and amino acids.

Optical isomers

A carbon atom bonded to four different groups is a chiral centre. The molecule can exist as two enantiomers, non-superimposable mirror images, which rotate plane-polarised light in opposite directions. Amino acids other than glycine have a chiral centre: in alanine, the central carbon is bonded to H, CH₃, NH₂ and COOH.

A racemic mixture contains equal amounts of the two enantiomers and has no overall optical activity. Chemical reactions without a chiral influence produce racemic mixtures. Yet the proteins of life on Earth are built almost entirely from L-amino acids.

Excesses in meteorites

Most amino acids in carbonaceous chondrites are close to racemic, as expected for non-biological synthesis. But some, notably isovaline, show an excess of the L-form. In the Murchison meteorite, isovaline L-excesses up to about 18% have been reported in some samples. Isovaline is rare in Earth's biosphere, which argues against contamination, and the excesses tend to be largest in samples that were most altered by water on the parent asteroid.

Hypotheses

Proposed causes include circularly polarised ultraviolet light in the star-forming region, which would destroy one enantiomer slightly faster than the other, followed by amplification of a small excess during aqueous alteration. If meteorites delivered amino acids with a slight L-excess to the early Earth, that could have biased the chemistry from which life emerged. This remains a hypothesis: there is evidence for each step, but not a complete chain.

Worked example

Enantiomeric excess

A meteorite extract contains isovaline with 59% L-enantiomer and 41% D-enantiomer. Calculate the enantiomeric excess, ee = (L − D)/(L + D) × 100%.

  1. L − D = 59 − 41 = 18.
  2. L + D = 59 + 41 = 100.
  3. ee = 18/100 × 100% = 18%.

Answer: An L-excess of 18%, among the largest reported for a meteoritic amino acid. A racemic sample would have ee = 0%.

Activity

Draw the two enantiomers of alanine as 3D wedge-and-dash structures and label the chiral centre. Then write a balanced evaluation (about 200 words) of the claim that meteorites explain why life uses L-amino acids, considering contamination, measurement and alternative explanations.

Quiz

5 questions. Choose an answer to see whether you are right and why. Finish the quiz to complete the lesson.

  1. Question 1What makes a carbon atom a chiral centre?

  2. Question 2Why is glycine not chiral?

  3. Question 3What is a racemic mixture?

  4. Question 4A sample has 70% L and 30% D. What is its enantiomeric excess?

  5. Question 5Why is isovaline useful evidence against contamination?

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