c07CarbohydratesandGlycobiology.

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246 Carbohydrates and Glycobiology

(a) D-Aldoses

Three carbons Four carbons Five carbons

H O H O H O H O
H O H O C C C C

H O C C H C OH HO C H H C OH HO C H
C H C OH HO C H H C OH H C OH HO C H HO C H
H C OH H C OH H C OH H C OH H C OH H C OH H C OH
CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH
D-Glyceraldehyde D-Erythrose D-Threose D-Ribose D-Arabinose D-Xylose D-Lyxose

Six carbons
H O H O H O H O H O H O H O H O
C C C C C C C C
H C OH HO C H H C OH HO C H H C OH HO C H H C OH HO C H
H C OH H C OH HO C H HO C H H C OH H C OH HO C H HO C H
H C OH H C OH H C OH H C OH HO C H HO C H HO C H HO C H
H C OH H C OH H C OH H C OH H C OH H C OH H C OH H C OH
CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH
D-Allose D-Altrose D-Glucose D-Mannose D-Gulose D-Idose D-Galactose D-Talose

FIGURE 7–3 Aldoses and ketoses. The series of (a) D-aldoses and
(b) D-ketoses having from three to six carbon atoms, shown as projec-
(b) D-Ketoses tion formulas. The carbon atoms in red are chiral centers. In all these D
Three carbons Four carbons isomers, the chiral carbon most distant from the carbonyl carbon has the
same configuration as the chiral carbon in D-glyceraldehyde. The sugars
CH2OH named in boxes are the most common in nature; you will encounter
CH2OH C O these again in this and later chapters.
C O H C OH
CH2OH CH2OH
Dihydroxyacetone D-Erythrulose a five- or six-membered ring results. Addition of the
second molecule of alcohol produces the full acetal or
ketal (Fig. 7–5), and the bond formed is a glycosidic
Five carbons Six carbons linkage. When the two molecules that react are both
monosaccharides, the acetal or ketal formed is a disac-
CH2OH CH2OH
charide.
CH2OH C O C O The reaction with the first molecule of alcohol cre-
C O H C OH HO C H ates an additional chiral center (the carbonyl carbon).
H C OH H C OH H C OH Because the alcohol can add in either of two ways,
attacking either the “front” or the “back” of the car-
H C OH H C OH H C OH
bonyl carbon, the reaction can produce either of two
CH2OH CH2OH CH2OH stereoisomeric configurations, denoted  and . For
D-Ribulose D-Psicose D-Fructose example, D-glucose exists in solution as an intramolecu-
lar hemiacetal in which the free hydroxyl group at C-5
CH2OH CH2OH has reacted with the aldehydic C-1, rendering the latter
CH2OH C O C O carbon asymmetric and producing two possible stereo-
C O H C OH HO C H isomers, designated  and  (Fig. 7–6). Isomeric forms
of monosaccharides that differ only in their configura-
HO C H HO C H HO C H
tion about the hemiacetal or hemiketal carbon atom are
H C OH H C OH H C OH called anomers, and the carbonyl carbon atom is called
CH2OH CH2OH CH2OH the anomeric carbon.
D-Xylulose D-Sorbose D-Tagatose Six-membered ring compounds are called pyranoses
because they resemble the six-membered ring compound