Disaccharides with a-connections Disaccharides with B-connections CH,OH CH,OH CH,OH CH,OH Maltose: a-D-glucopyranosyl (1-4)a-D-glucopyranose Cellobiose: H. H. OH B-D-glucopyranosyl (1-4)8-D-glucopyranose H OH H но ОН Н но ОН Н OH H OH H OH OH H. OH OH a-D-Glc a-D-Glc B-D-Glc B-D-Glc CH,OH H. OH CH,OH CH,OH a,a-Trehalose: a-D-glucopyranosyl (1-1)a-D-glucopyranose Lactose: H. ОН Н B-D-galactopyranosyl (1-4)8-D-glucopyranose Но OH ΟΗ Η ОН Н ΟΗ Η H Но OH H OH H OH OH a-D-Glc a-D-Glc B-D-Gal B-D-Glc CH,OH CH,OH CH,OH CH, Sucrose: a-D-glucopyranosyl (1-2)B-D-fructofuranoside Gentiobiose: B-D-glucopyranosyl (1-6)8-D-glucopyranose H. H. OH OH H ОН Н но н но CH,OH ОН Н H. Но но OH OH H OH H a-D-Glc B-D-Fru B-D-Glc B-D-Glc (a) Disaccharides linked through the C-1 of the a anomer: maltose, trehalose, and sucrose. (b) Disaccharides with B linkage: cellobiose, lactose, and gentiobiose. A FIGURE 9.14 Structures of some important disaccharides. Shown are Haworth projections of the same molecules, with color-coded monomers: blue = glucose, pink = fructose, teal = galactose. Note the convention used to draw gly- cosidic bonds between monomers in disaccharides. The "curved bonds" allow the Haworth projections of the monomers to be drawn on the same line. 우

Biochemistry

9th Edition

ISBN:9781319114671

Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Chapter1: Biochemistry: An Evolving Science

Section: Chapter Questions

Problem 1P

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Question

A reducing sugar will undergo the Fehling reaction, which requires a(potential) free aldehyde group. Which of the disaccharides shown inFigure are reducing and which are nonreducing?

Disaccharides with a-connections
Disaccharides with B-connections
CH,OH
CH,OH
CH,OH
CH,OH
Maltose:
a-D-glucopyranosyl
(1-4)a-D-glucopyranose
Cellobiose:
H.
H.
OH
B-D-glucopyranosyl
(1-4)8-D-glucopyranose
H
OH H
но
ОН Н
но
ОН Н
OH H
OH
H
OH
OH
H.
OH
OH
a-D-Glc
a-D-Glc
B-D-Glc
B-D-Glc
CH,OH
H.
OH
CH,OH
CH,OH
a,a-Trehalose:
a-D-glucopyranosyl
(1-1)a-D-glucopyranose
Lactose:
H.
ОН Н
B-D-galactopyranosyl
(1-4)8-D-glucopyranose
Но
OH
ΟΗ Η
ОН Н
ΟΗ Η
H
Но
OH
H
OH
H
OH
OH
a-D-Glc
a-D-Glc
B-D-Gal
B-D-Glc
CH,OH
CH,OH
CH,OH
CH,
Sucrose:
a-D-glucopyranosyl
(1-2)B-D-fructofuranoside
Gentiobiose:
B-D-glucopyranosyl
(1-6)8-D-glucopyranose
H.
H.
OH
OH H
ОН Н
но
н но
CH,OH
ОН Н
H.
Но
но
OH
OH
H
OH
H
a-D-Glc
B-D-Fru
B-D-Glc
B-D-Glc
(a) Disaccharides linked through the C-1 of the a anomer:
maltose, trehalose, and sucrose.
(b) Disaccharides with B linkage:
cellobiose, lactose, and gentiobiose.
A FIGURE 9.14 Structures of some important disaccharides. Shown are Haworth projections of the same molecules,
with color-coded monomers: blue = glucose, pink = fructose, teal = galactose. Note the convention used to draw gly-
cosidic bonds between monomers in disaccharides. The "curved bonds" allow the Haworth projections of the monomers
to be drawn on the same line.
우

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

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