The D-Aldoses:
(CH2O)x: X = 3 to 6
O
(CH2O)3
HO
H
OH
D-glyceraldehyde
Kiliani-Fisher Synthesis
1) HCN
2) DibalH or
H2, Pd/BaSO4
3) H3O+
OH
(CH2O)4
OH
H
HO
or
OH
H
HO
O
OH
D-erythrose
O
D-threose
1) HCN
2) DibalH or
H2, Pd/BaSO4
3) H3O+
OH
(CH2O)5
OH
O
HO
H
OH
or
O
OH
HO
H
OH
OH
HO
OH
H
OH
or
H
OH
OH
D-Lyxose
1) HCN
2) DibalH or
H2, Pd/BaSO4
3) H3O+
1) HCN
2) DibalH or
H2, Pd/BaSO4
3) H3O+
OH
OH
OH
H
HO
OH
OH
OH
O
OH
H
HO
OH
D-Allose
(CH2O)6
O
HO
OH
D-Xylose
D-Arabinose
D-Ribose
OH
O
OH
OH
OH
OH
O
D-Altrose
C-2,3-bis-epi-glucose
OH
OH
H
HO
OH
OH
O
D-Mannose
C-2-epi-glucose
OH
O
D-Galactose
C-4-epi-glucose
or
OH
OH
H
HO
OH
H
OH
or
OH
HO
O
or
OH
H
HO
OH
D-Gulose
C-3,4-bis-epi-glucose
or
OH
HO
O
OH
H
D-Glucose
C-3-epi-glucose
OH
OH
OH
O
D-Idose
C-2,3,4-tris-epi-glucose
OH
H
HO
OH
OH
O
D-Talose
C-2,4-bis-epi-glucose
α-hexoses
Hexoses: (CH2O)6
D-Sugars
CHO
D-Glucose
(CH2O)6
OH
OH
H
HO
OH
OH
O
CHO
H
OH
H
OH
HO
H
H
OH
HO
H
H
OH
H
OH
CH2OH
H
pyranose
form
OH
HO
OH
CH2OH
α-Glucose
OH OH
O
HO
HO
OH
OH
OH
HO
HO
D-β-glucose
O
OH
OH OH
OH
OH
D-β-glucose
β-isomers
OH
OH
α−Mannose
O
HO
OH
O
OH
pyranose
form is more
stable!
OH
OH
furanose
form
OH
OH
O
α-allose
α-isomers
OH
pyranose
form is more
stable!
O
HO
HO
OH
HO
O
HO
OH
HO
OH
O
OH
OH
HO
α-Galactose
HO
OH
OH
OH
D-α-glucose
D-α-glucose
HO
O
OH OH
OH
α-Gulose
trans so alpha (α)
cis so beta (β)
OH
OH
HO
HO
HO
HO
OH
x
OH
x
OH
Alpha (α)/Beta (β) refers to
the cis/trans relationship
between the anomeric hydroxyl
group and the terminal carbon
when the sugar is in a cyclized
form between the hydroxyl
group on the penultimate
carbon and the carbonyl.
OH
X =1; D-α-glucose
X =1; D-β-glucose
The Anomeric Effect:
lone pair
aligns with
polarized
bond
acid
or
base
catalyzed
O
2H-pyran
4H-pyran
OH
OH OH
α-idose
OH
OH
O
OH OH
The Anomeric Effect:
O
H
O
OH
OH
α-altrose
OH
OH
Axial OH
More Stable!
O
OH
O
O
O
Alpha (α)/Beta (β) does not
refer to either axial or
equatorial.
H
O
O
tetrahydropyran
furan
OH
Usually the α-isomer is
more stable than the βisomer
OH
OH
O
OH
α-talose
α-1,4'-glycosyl linkage
O
tetrahydro-furan
OH
HO
HO
OH
O
HO
O
HO
Maltose
(glu/glu)
OH
O
HO
OH
Hexoses: (CH2O)6
The Anomeric Effect:
lone pair
aligns with
polarized
bond
acid
or
base
catalyzed
O
O
H
OH
OH
Axial OH
More Stable!
H
The Anomeric Effect:
Usually the α-isomer is
more stable than the βisomer
trans so alpha (α)
cis so beta (β)
Alpha (α)/Beta (β) does not
refer to either axial or
equatorial.
OH
OH
O
O
HO
HO
HO
HO
OH
x
x
OH
OH
OH
X =1; D-α-glucose
X =1; D-β-glucose
Mecahnism for anomer isomerization
Alpha (α)/Beta (β) refers to
the cis/trans relationship
between the anomeric hydroxyl
group and the terminal carbon
when the sugar is in a cyclized
form between the hydroxyl
group on the penultimate
carbon and the carbonyl.
OH
OH
H+
O
HO
HO
O
OH
HO
HO
OH
OH
H+
H+
equatorial
atack
H2O
OH
OH
OH
O
HO
HO
OH2
OH
OH
O
O
HO
HO
HO
HO
OH
HO
OH2
axial
atack
H2O
Mecahnism for α-glycoside synthesis
OH
OH
H+
O
HO
HO
O
OH
HO
HO
ROH
OH
OH
H+
RO
H+
OH
OH
OH
O
HO
HO
OH2
OH
O
O
HO
HO
HO
HO
OH
HO
ROH
axial
atack
H
O
R
Carbohydrates: (CH2O)x
The Hexoses
(CH2O)6
CHO
D-Glucose
(CH2O)6
OH
H
OH
HO
H
HO
OH
OH
H
O
H
CHO
OH
H
H
HO
OH
H
OH
H
CH2OH
OH
HO
OH
H
H
HO
OH
OH
O
OH
CHO
H
HO
OH
H
HO
H
HO
HO
H
HO
CH2OH
H
OH
H
H
CH2OH
O
O
O
O
2H-pyran
4H-pyran
tetrahydropyran
furan
O
tetrahydro-furan
pyranose
form
furanose
form
O
HO
HO
OH
pyranose
form is more
stable!
OH
β-isomer
H
OH
CH2OH
CHO
L-Glucose
(CH2O)6
OH
OH
O
HO
OH
β-isomer
OH
HO
D-β-glucose
OH
D-β-glucose
The Anomeric Effect:
Usually the α-isomer is
more stable than the βisomer
OH
OH
pyranose
form is more
stable!
O
α-isomer
HO
HO
OH
O
HO
HO
OH
β-hexoses
O
HO
HO
β-Glucose
OH
OH
OH
α-hexoses
D-Sugars
OH
Glucose
all equatorial
pyran substituents
α-isomer
D-α-glucose
D-α-glucose
L-Sugars
OH
L-Sugars
HO
HO
OH
OH
OH
OH
O
OH
β-Glucose
O
HO
D-Sugars
OH
OH
HO
HO
OH
α-Glucose
OH
O
OH
α-Glucose
OH
OH
O
The Hexoses
O
HO
HO
HO
OH
D-α-glucose
HO
D-β-glucose
OH
OH
β-hexoses
L-Sugars
α-hexoses
OH
OH
O
HO
HO
OH
O
OH
HO
HO
OH
HO
OH
HO
OH
OH
HO
HO
OH
OH
OH
O
OH
OH
HO
Idose
C-2/3/4 epi-glucose
C-2/3/4 axial OH's
OH
O
OH
HO
HO
OH
HO
OH
OH
HO
β-talose
HO
O
OH OH
OH
α-Gulose
OH
OH
OH
OH
O
OH
OH
OH
OH
OHOHOH
α-talose
OH
O
OH OH
O
OH
OH
OH OH
α-altrose
O
α-Galactose
α-idose
OH
OH
HO
O
OH
OH
OH
OH
OH
HO OH
OH
β-talose
OH
α-idose
HO
O
OH
OH
O
OH
O
OH
OH
β-altrose
OH
OH
OH
HO
O
OH
O
OH
OH
O
β-altrose
Talose
C-2/4 epi-glucose
C-2/4 axial OH's
OH
OH
HO
OH
α-Gulose
OH
β-idose
OH OH
β-idose
HO
OH
β-Gulose
OH
OH
OH
O
HO
O
HO
OH
OH
HO
α-Galactose
OH
HO
HO
OH
α-allose
OH OH
β-Galactose
β-Gulose
Altrose
C-2/3 epi-glucose
C-2/3 axial OH's
O
O
OH
OH
HO
O
OH OH
OH
OH
OH
β-Galactose
Gulose
C-3/4 epi-glucose
C-3/4 axial OH's
HO
HO
HO
OH
α-allose
OH
HO
OH
O
HO
OH
OH
α−Mannose
OH
OH
O
β-allose
β-allose
Galactose
C-4 epi-glucose
C-4 axial OH
HO
OH
O
OH
α−Mannose
OH
OH
OH OH
HO
OH
O
OH
O
HO
β−Mannose
OH
O
HO
OH
α-Glucose
OH
OH
O
OH
O
OH
β−Mannose
Allose
C-3 epi-glucose
C-3 axial OH
HO
α-Glucose
OH
OH
OH
OH
HO
β-Glucose
O
O
HO
OH
OH
D-Sugars
OH
OH
OH
HO
HO
β-Glucose
Mannose
C-2 epi-glucose
C-2 axial OH
L-Sugars
D-Sugars
OH
Glucose
all equatorial
pyran substituents
OH
OH
α-altrose
OH
OH
OH
O
OH
α-talose
OH
OH
OH
Carbohydrates: (CH2O)5
O
O
OH
OH
Carbohydrate
portions of
DNA nd RNA
The Pentoses: (CH O)
2
D-Arabinose
(CH2O)5
OH
CHO
O
HO
HO
H
H
OH
OH
HO
2-Deoxy-α/β-D-Ribose
HO
OH
α/β-D-Ribose
5
H
D-Arabinose
CHO
H
OH
HO
H
OH
H
CH2OH
OH
O
H
OH
OH
CH2OH
cis so Beta (β)
OH
HO
O
OH
OH
OH
O
α/β-D-Arabinose
OH
Pyranose form
HO
OH
Furanose form
HO
D-Ribose
(CH2O)5
OH
CHO
O
HO
H
OH
OH
OH
OH
H
H
OH
OH
H
OH
H
OH
CH2OH
OH
Furanose form
trans so alpha (α)
OH
CH2OH
O
OH
OH
O
HO
O
OH
α/β-D-Ribose
OH
HO
OH
OH
OH
HO
OH
Furanose form
Pyranose form
D-Xylose
(CH2O)5
OH
CHO
O
HO
H
HO
H
OH
OH
H
D-Xylose
Alpha (α)/Beta (β) does not
refer to either axial or
equatorial.
CHO
OH
H
H
HO
OH
H
CH2OH
OH
H
OH
CH2OH
OH
O
HO
O
OH
OH
HO
OH
HO
OH
Furanose form
Pyranose form
D-Lyxose
(CH2O)5
OH
CHO
O
HO
HO
HO
H
OH
OH
H
D-Lyxose
HO
CHO
H
H
HO
HO
OH
H
H
H
CH2OH
OH
O
α/β-D-Lyxose
CHO
H
H
D-Ribose
α/β-D-Xylose
OH
OH
CH2OH
OH
OH
O
OH
HO
Pyranose form
HO
OH
Furanose form
Alpha (α)/Beta (β) refers to
the cis/trans relationship
between the anomeric hydroxyl
group and the terminal carbon
when the sugar is in a cyclized
form between the hydroxyl
group on the penultimate
carbon and the carbonyl.
The Disaccharides
α-1,4'-glycosyl linkage
OH
O
HO
HO
HO
β-1,4'-glycosyl linkage
OH
O
O
HO
HO
OH
OH
O
HO
HO
O
HO
HO
OH
Maltose
(glu/glu)
β-1,4'-glycosyl linkage
HO
O
HO
OH
O
HO
HO
OH
Cellobiose
(glu/glu)
OH
O
HO
O
HO
OH
Lactose
(gal/glu)
β-1,3'-glycosyl linkage
CO2–
O
HO
HO
HO
OH
O
HO
O
OH
O
HO
HO
Ac
OH
N
2-acetyl-glucosamine
(gluNAc)
OH
H
H2N
HO2C
O
HO
HO
HO
Hyalobiuronic Acid
glucuonic acid
OH
Blood-type Di/Trisaccharides
OH OH
OH OH
O
HO
Ac N
H
OH OH
O
O
O
HO
HO
OMembrane Protein
OH OH
OH OH
O
O
O
O
OH
OH
OH
OH
OMembrane Protein
Blood type-A
O
OH
OH
O
Ac N
H
OH
OH
OH
Blood type-B
Blood type-O
OH OH
HO
OMembrane Protein
O
O
O
O
HO
OH
OH
N-Acetylgalactosamine
(galNAc)
O
OH
OH
6-deoxy-galactose
OH
The Oligosaccharides
α-1,4'-glycosyl linkage
OH
O
HO
HO
HO
α-1,4'-glycosyl linkage
O
HO
HO
HO
OH
HO
Amylose
(glu)x
O
HO
HO
O
O
HO
OH
OH
O
OH
O
HO
x
β-1,4'-glycosyl linkage
β-1,4'-glycosyl linkage
O
OH
Cellulose
(glu)x
β-1,4'-glycosyl linkage
β-1,4'-glycosyl linkage
OH
OH
O
Ac
O
HO
HO
x
HO
OH
HO
HO
OH
O
N
O
O
HO
N
Ac
H
H
OH
O
O
HO
N
x
Ac
H OH
OH
O
HO
HO
N
Ac
Chitin
(gluNAc)x
OH
2-acetylamino-2-deoxy-glucose
(gluNAc)
H
The clinicaly used Oligosaccharides
HO
HO
CO2–
O
HO
OH
O
HO
CO2–
O
O
O
H N HO
Ac
HO
x
O
HO
HO2C
HO
O
O
HO
HO
HO
OH
O
O
CO2–
O
OH
HO
H N
Ac
–O
N
3S
α-1,4'-glycosyl linkage
CO2–
O
Ac
OSO3–
x
O
O
H HO
–O SO
3
OH
O
HO
HO
O
CO2–
HO
O
N
–O S
O
3
H HO
–O SO
3
heparin
OH
N
2-acetyl-glucosamine
(gluNAc)
OH
H
HO2C
O
HO
HO
HO
glucuonic acid
OH
Aminoglycoside Antibiotics:
Deoxy/Amino Sugars
R
HO
HO
O
H2N
NH2
NH2
HO
O
Kanamycin
A: R = NH2, R'= OH HO
B: R = NH2, R'= NH2
C: R = OH, R'= NH2
NH2
O
HO
R'
O
HO
O
H2N
OH
H2N
Hyalobiuronic Acid
α-1,4'-glycosyl linkage
HO
HO
O
HO
Hyaluronic Acid
anticoagulant
OSO3–
O
OH
OH
H2N
NH2
NH2
O
HO
O
HO
NH2
Tobramycin
H2N
OH
O
O
OH
NH2
O
HO
NH2
O
HO
Dibekacin
HO
O
OH
NH2
Amino Sugars