Which of the other three D aldopentoses gives the same aldaric acid as D-lyxose?

Name: Problem 51, Chapter 21: Organic chemistry with biological applications
Uploaded: 2020-06-01T21:18:16-08:00
Duration: 3 min 27 s
Channel: Ricajoy Montero
Description: Which of the other three D aldopentoses gives the same aldaric acid as D-lyxose?

step 1 Problem 52. We have the structure for the life cells over here and we're figuring out the alderi

Which of the other three D aldopentoses gives the same...

Key Concepts

Aldopentoses

Aldopentoses are five?carbon sugars featuring an aldehyde group at the top (in the Fischer projection) and a primary –CH2OH group at the bottom. They have three chiral centres (at C2, C3, and C4) and can exist in several stereoisomeric forms. Their stereochemistry, as depicted in Fischer projections (with hydroxyl groups on the right or left), underpins their chemical behavior and biological roles.

Aldaric Acids

Aldaric acids are dicarboxylic acids obtained by the oxidation of aldoses in which both the aldehyde and the primary alcohol groups are converted into carboxylic acid groups. Importantly, the oxidation process preserves the stereochemistry at the internal carbons. Because numbering can be done from either end (since both termini are now carboxyl groups), the configuration sequence of the chiral centres is effectively considered up to reversal.

Stereochemical Equivalence upon Oxidation

When an aldose is oxidized to its corresponding aldaric acid, only the configuration of the internal chiral centres matters. If the sequence of configurations is the reverse of that in another sugar, the two oxidation products may be identical. In the specific case of D?lyxose, the configuration of its three internal centres (when viewed in the conventional order) is self-reciprocal, meaning that reversed it gives the same sequence. Thus, in the set of D aldopentoses, no other sugar has the necessary reversed stereochemical sequence to yield the identical aldaric acid as that obtained from D?lyxose.

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