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Feodor Lynen
Konrad Bloch
A sterol with 27 carbon molecules with
an -OH group at the # 3 position
Hydrocarbon tail
22 24
21 26
25
20 23
18
CH3
12 17 27
11 13 16
19
C27H45OH
CH3 14 15
1 9
2 10 8
3 5 7 4 Hydrocarbon Rings
OH 4
6 3 Hydroxy cholesterol
Cholesterol
Biosynthesis
2
4
Cholesterol Synthesis: Stage 1
Thiolase is an oxidant
enzyme (removes
electrons)
HMG-CoA
β-hydroxy-β-methylglutaryl-CoA
5 Carbon units
In the second step, mevalonate is phosphorylated from ATP to isoprene units or
isoprenoids, namely isopentyl pyrophosphate, which can isomerize or interconvert to
dimethylallyl pyrophosphate
Cholesterol +
Synthesis:
Stage 3
10 carbon intermediate
30 carbon intermediate
Squalene
Cholesterol
Synthesis:
Stage 4 A series of reactions -
oxidation, cyclization, and
loss of three methyl groups -
results in conversion of
squalene to cholesterol.
27carbon molecule
Cholesterol
Cholesterol Synthesis
Acetate Acetoacetyl-CoA
HMG synthase
Dimethylallyl-PP
HMGCoA
HMG CoA reductase isomerization
Mevalonate Isopentyl-pyrophosphate
condensation
Farnesyl-pyrophosphate
Squalene
Squalene synthase Isoprenoids
Lanosterol Cholesterol
4 ringed structure
19-20 reactions including
Desmosterol, Lathosterol