Book says threonine has chiral center in its sidechain? How?

Click For Summary
SUMMARY

Threonine and isoleucine possess a chiral center in their sidechains, specifically at the carbon adjacent to the alpha carbon. This carbon is bonded to four distinct substituents: an oxygen atom, a hydrogen atom, a methyl group, and the alpha carbon itself. The distinction between substituents is crucial for determining chirality; in this case, the methyl group and the alpha carbon are considered different substituents, confirming the chirality of threonine's sidechain. Understanding the definition of chirality is essential for accurate biochemical analysis.

PREREQUISITES
  • Basic understanding of amino acid structure
  • Knowledge of chirality in organic chemistry
  • Familiarity with substituent classification
  • Understanding of carbon bonding and hybridization
NEXT STEPS
  • Study the concept of chirality in organic compounds
  • Learn about amino acid structures and their properties
  • Research the role of chiral centers in biological molecules
  • Explore stereochemistry and its implications in biochemistry
USEFUL FOR

Biochemists, organic chemists, students studying amino acid structures, and anyone interested in the stereochemical properties of biomolecules.

ppppparker
Messages
18
Reaction score
4
Text says that threonine and isoleucine have a chiral carbon in sidechain. I am not seeing it.

The carbon in the sidechain that is next to the alpha carbon is attached to an oxygen, a hydrogen, a carbon (a methyl group) and the alpha carbon. So that means its attached to two carbons, so therefore it doesn't have 4 different substituents attached so therefore its not chiral.
Its probably something to do with me not grasping definition of chiral I am geussing, ..
do you consider the atoms attached or is it the substituents that must be different for chirality? For example, would CH and a CH2 be considered two different substits?
thanks
 
Chemistry news on Phys.org
The substituents must be different, so the methyl group and alpha carbon count as two different substituents.
 

Similar threads

  • · Replies 4 ·
Replies
4
Views
2K
Replies
2
Views
2K
  • · Replies 8 ·
Replies
8
Views
8K
  • · Replies 1 ·
Replies
1
Views
7K
  • · Replies 6 ·
Replies
6
Views
2K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 1 ·
Replies
1
Views
19K
  • · Replies 1 ·
Replies
1
Views
2K
Replies
31
Views
4K
Replies
1
Views
12K