Learn · Organic Chemistry

D and L Notation for Sugars

An older configurational label, defined relative to glyceraldehyde.

Quick answer Draw the sugar as a Fischer projection with the carbonyl at the top, then look at the bottom-most stereocenter: OH on the right means D, OH on the left means L. This reference-carbon label is not the same as (+)/(−) rotation or (R)/(S).

1. D and L are configurational labels defined relative to glyceraldehyde.

Glyceraldehyde (the reference)

2. Draw the sugar as a Fischer projection with the carbonyl (CHO) at the top.

Carbon 1 (CHO) sits at the top of the Fischer chain

3. Read the bottom-most (highest-numbered) stereocenter to assign the letter.

D-erythrose — OH on the reference carbon points right, so it is a D-sugar

4. D-glyceraldehyde and L-glyceraldehyde are non-superimposable mirror images.

D-glyceraldehyde
L-glyceraldehyde

5. Almost all natural sugars are D, while most natural amino acids are L.

L-alanine — the common amino-acid form

6. D and L is not the same as (+)/(−) rotation or (R)/(S) configuration.

Lactic acid — a single reference-carbon label says nothing about how it rotates light

Summary: Reference is glyceraldehyde · CHO at top of the Fischer projection · read the bottom stereocenter · OH right = D, OH left = L · sugars mostly D, amino acids mostly L · D/L ≠ (+)/(−) ≠ R/S.

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Glyceraldehyde. Its two enantiomers, D- and L-glyceraldehyde, define the labels for all other sugars and amino acids.

The bottom-most stereocenter — the highest-numbered chiral carbon, farthest from the carbonyl. OH on the right is D; OH on the left is L.

No. D/L describes only the reference carbon’s configuration; it is independent of (+)/(−) optical rotation and of (R)/(S) descriptors.

L. Most natural amino acids are L-configured, whereas almost all natural sugars are D.

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