10/21/24, 4:07 PM Carbohydrates mathews.
pdf (Part 2)
Carbohydrates mathews.pdf
(Part 2)
Carbohydrates: Sugars, Sacc
harides, Glycans
Structural Diversity of Carbohydrat
es
Carbohydrates are compounds with the general formula (CH2O)n, o
r derivatives of such compounds (9.1)
Monosaccharides exist as enantiomeric pairs (D and L) and multiple
diastereomers due to the presence of chiral centers (9.2)
Monosaccharides can be classified as aldoses or ketoses based on
the presence of an aldehyde or ketone group (9.2)
Monosaccharides form cyclic structures (furanose or pyranose) thro
ugh internal hemiacetal formation, resulting in α or β anomers (9.3)
Carbohydrate derivatives include phosphate esters, glycosides, ami
no sugars, and uronic acids (9.4)
Oligosaccharides and Polysacchari
des
Oligosaccharides and polysaccharides are formed by glycosidic link
ages between monosaccharides (9.5)
Polysaccharides serve diverse functions, including energy storage (s
tarch, glycogen), structural roles (cellulose, chitin), and cell surface i
dentification (glycoproteins, blood group antigens) (9.6)
The glycosidic linkage is metastable, and enzymes control its hydrol
ysis in vivo (9.5)
Glycoconjugates
Glycoproteins are proteins with covalently attached oligosaccharide
or polysaccharide chains (9.7)
N-linked and O-linked glycans are attached to proteins through diff
erent mechanisms (9.7)
The blood group antigens are important examples of O-linked oligos
accharides on cell surfaces (9.8)
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10/21/24, 4:07 PM Carbohydrates mathews.pdf (Part 2)
Erythropoietin is a glycoprotein with both O- and N-linked oligosacc
harides (9.8)
Influenza neuraminidase is a viral enzyme that is a target for antivira
l drugs (9.8)
Oligosaccharides as Cell Markers
Cell surfaces are often coated with a thick layer of polysaccharides
called the glycocalyx, which interacts with other substances (9.9)
Lectins and selectins are proteins that bind to specific carbohydrate
structures, playing roles in cell-cell interactions and the inflammator
y response (9.9)
Biosynthesis of Glycoconjugates
Amino sugars like glucosamine are derived from fructose-6-phosph
ate through an amidotransferase reaction (9.10)
Nucleotide-linked sugars are the activated intermediates used in gl
ycoconjugate synthesis (9.10)
The biosynthesis of N-linked glycans involves a lipid-linked oligosac
charide intermediate that is transferred to the polypeptide chain (9.1
1)
Processing of N-linked glycans occurs as the glycoprotein moves thr
ough the ER and Golgi, with the oligosaccharide structure serving as
a targeting signal (9.11)
Bacterial cell wall peptidoglycan is synthesized outside the cell using
a lipid-linked intermediate, with the cross-linking reaction targeted
by antibiotics like penicillin (9.12)
The O antigen of Gram-negative bacteria is also assembled on a lipi
d carrier and then transferred to the cell surface (9.13)
Key Concepts
Carbohydrates exhibit immense structural diversity due to theNotes
presence of chiral centers, cyclic structures, and various linkages an
d modifications (9.1-9.4)
Polysaccharides serve diverse biological functions, including energy
storage, structural roles, and cell surface identification (9.6)
Glycoproteins contain covalently attached oligosaccharide chains t
hat play important roles in cell-cell interactions and molecular reco
gnition (9.7-9.8)
Cell surfaces are often coated with a glycocalyx of polysaccharides
that interact with other molecules and cells (9.9)
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Glycoconjugate biosynthesis involves the use of nucleotide-linked a
nd lipid-linked activated intermediates, with the oligosaccharide str
ucture serving as a targeting signal (9.10-9.13)
Table: Major Types of N-Linked Oligosacchari
des
Type Structure
Branched structure with terminal sialic acid, galactose, a
Complex
nd fucose residues
Combination of high-mannose and complex-type oligos
Hybrid
accharides
High-mann Contains only mannose residues beyond the core pentas
ose accharide
End of
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