Biosynthesis of sitosterol from 2(R)- and (2S)-[2-3H]mevalonic acid in the pea. Incorporation of a 15.alpha.-tritium atom derived from (3RS, 2R)-[2-14C,2-3H]mevalonic acid

1975 ◽  
Vol 97 (13) ◽  
pp. 3820-3822 ◽  
Author(s):  
Eliahu Caspi ◽  
Jacek Sliwowski ◽  
Caron S. Robichaud
Keyword(s):  
Mevalonic Acid ◽  
Tritium Atom

scholarly journals Incorporation of [2−14C,(5R)-5−3H1]mevalonic acid into cholesterol by a rat liver homogenate and into β-sitosterol and 28-isofucosterol by Larix decidua leaves

1969 ◽  
Vol 114 (4) ◽  
pp. 885-892 ◽  
Author(s):  
L J Goad ◽  
G. F. Gibbons ◽  
Loretta M. Bolger ◽  
H H Rees ◽  
T W Goodwin
Keyword(s):  
Double Bond ◽  
Hydrogen Atom ◽  
Rat Liver ◽  
Cholesterol Biosynthesis ◽  
Liver Homogenate ◽  
Mevalonic Acid ◽  
Atomic Ratio ◽  
Larix Decidua ◽  
Tritium Atom

1. Incubation of a rat liver homogenate with 3R-[2−14C,(5R)-5−3H1]mevalonic acid gave cholesterol with 3H/14C atomic ratio 6:5. 2. Conversion of the labelled cholesterol into 3β-acetoxy-6-nitrocholest-5-ene or cholest-4-ene-3,6-dione resulted in the loss of one tritium atom from C-6. 3. These results show that during cholesterol biosynthesis the 6α-hydrogen atom of a precursor sterol is eliminated during formation of the C-5–C-6 double bond. 4. Incorporation of 3R-[2−14C,(5R)-5−3H1]mevalonic acid into the sterols of larch (Larix decidua) leaves gave labelled cycloartenol and β-sitosterol with 3H/14C atomic ratios 6:6 and 6:5 respectively. 5. One tritium atom was lost from C-6 on conversion of the labelled β-sitosterol into either 3β-acetoxy-6-nitrostigmast-5-ene or stigmast-4-ene-3,6-dione, demonstrating that formation of the C-5–C-6 double bond of phytosterols also involves the elimination of the 6α-hydrogen atom of a precursor sterol. 6. The 3R-[2−14C,(5R)-5−3H1]mevalonic acid was also incorporated by larch (L. decidua) leaves into a sterol that co-chromatographed with 28-isofucosterol. Confirmation that the radioactivity was associated with 28-isofucosterol was obtained by co-crystallization with carrier 28-isofucosterol and ozonolysis of the acetate to give radioactively labelled 24-oxocholesteryl acetate. 7. The significance of these results to phytosterol biosynthesis is discussed.

Stereochemistry of tritium at C-1 and C-7 in cholesterol derived from (3R,2R)-2T-mevalonic acid

1968 ◽  
Vol 9 (35) ◽  
pp. 3829-3832 ◽  
Author(s):  
E. Caspi ◽  
J.B. Greig ◽  
P.J. Ramm ◽  
K.R. Varma
Keyword(s):  
Mevalonic Acid

scholarly journals Mevalonic Acid Pyrophosphate and Isopentenylpyrophosphate

1959 ◽  
Vol 234 (10) ◽  
pp. 2595-2604 ◽  
Author(s):  
Konrad Bloch ◽  
S. Chaykin ◽  
A.H. Phillips ◽  
A. de Waard
Keyword(s):  
Mevalonic Acid

scholarly journals Cholesterol synthesis in rat liver peroxisomes. Conversion of mevalonic acid to cholesterol.

1987 ◽  
Vol 262 (36) ◽  
pp. 17420-17425 ◽  
Author(s):  
S L Thompson ◽  
R Burrows ◽  
R J Laub ◽  
S K Krisans
Keyword(s):  
Rat Liver ◽  
Cholesterol Synthesis ◽  
Mevalonic Acid ◽  
Liver Peroxisomes

scholarly journals Enzymatic Synthesis of Rubber from Mevalonic Acid

1958 ◽  
Vol 233 (2) ◽  
pp. 340-343
Author(s):  
Roderic B. Park ◽  
James Bonner
Keyword(s):  
Enzymatic Synthesis ◽  
Mevalonic Acid
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