Biosynthesis and structure of a new intermediate between farnesyl pyrophosphate and squalene.
作者： G Popják , J Edmond , K Clifford , V Williams
DOI: 10.1016/S0021-9258(18)91765-5
关键词:
摘要: Abstract The intermediate, discovered by Rilling, between farnesyl pyrophosphate and squalene was synthesized in milligram quantities with yeast subcellular particles from farnesyl-14C-pyrophosphate farnesyl-1-3H2-14C-pyrophosphate. 3H:14C ratio the new precursor found to be identical that pyrophosphate, whereas close expected value of 0.75 relative either or precursor. is optically active gives a normal optical (dextro) rotatory dispersion curve. From nuclear magnetic resonance mass spectrometric studies, chemical degradation, it concluded this cyclic pyrophosphoryl ester squalene-10,11-glycol. metabolism yields, addition precursor, free farnesol, some nerolidol, farnesene, also monophosphate (phosphodiester) latter not converted into liver microsomes NADPH. synthesis could shown. In absence NADPH, quantitatively phosphodiester squalene-10,11-glycol, which thought arise enzymic hydrolysis A method for preparation crystalline purification described.
sci-hub.st 参考文章(19)
G. Popják, J.W. Cornforth, Rita H. Cornforth, R. Ryhage, DeWitt S. Goodman, Studies on the Biosynthesis of Cholesterol XVI. CHEMICAL SYNTHESIS OF 1-H23-2-C14- AND 1-D2-2-C14-TRANS-TRANS-FARNESYL PYROPHOSPHATE AND THEIR UTILIZATION IN SQUALENE BIOSYNTHESIS Journal of Biological Chemistry. ,vol. 237, pp. 56- 61 ,(1962) , 10.1016/S0021-9258(18)81360-6
G. Popják, DeWitt S. Goodman, J.W. Cornforth, Rita H. Cornforth, R. Ryhage, Studies on the biosynthesis of cholesterol. XV. Mechanism of squalene biosynthesis from farnesyl pyrophosphate and from mevalonate. Journal of Biological Chemistry. ,vol. 236, pp. 1934- 1947 ,(1961) , 10.1016/S0021-9258(18)64109-2
Mildred Cohn, Thomas R. Hughes, Phosphorus magnetic resonance spectra of adenosine di- and triphosphate. I. Effect of pH. Journal of Biological Chemistry. ,vol. 235, pp. 3250- 3253 ,(1960) , 10.1016/S0021-9258(20)81346-5
G. Popják, L. Gosselin, Irene Youhotsky Gore, R. G. Gould, Studies on the biosynthesis of cholesterol. 6. Coenzyme requirements of liver enzymes for synthesis of squalene and of sterol from DL-3-hydroxy-3-methyl-[2-14C] pentano-5-lactone. Biochemical Journal. ,vol. 69, pp. 238- 248 ,(1958) , 10.1042/BJ0690238
H.C. Rilling, A New Intermediate in the Biosynthesis of Squalene Journal of Biological Chemistry. ,vol. 241, pp. 3233- 3236 ,(1966) , 10.1016/S0021-9258(18)96520-8
Richard C. Larock, Reagents for Organic Synthesis ,(1967)
J. W. Cornforth, Rita H. Cornforth, G. Popják, Irene Youhotsky Gore, Studies on the biosynthesis of cholesterol. 5. Biosynthesis of squalene from DL-3-hydroxy-3-methyl [2-14C] pentano-5-lactone. Biochemical Journal. ,vol. 69, pp. 146- 155 ,(1958) , 10.1042/BJ0690146
Morris London, Perry B. Hudson, Studies on the purification of acid prostatic phosphatase Archives of Biochemistry and Biophysics. ,vol. 46, pp. 141- 153 ,(1953) , 10.1016/0003-9861(53)90177-5
J.W. Cornforth, R.H. Cornforth, C. Donninger, G. Popják, G. Ryback, G.J. Schroepfer, Stereospecific insertion of hydrogen atom into squalene from reduced nicotinamide-adenine dinucleotides Biochemical and Biophysical Research Communications. ,vol. 11, pp. 129- 134 ,(1963) , 10.1016/0006-291X(63)90079-2
Gopal Krishna, Howard W. Whitlock, Donald H. Feldbruegge, John W. Porter, Enzymic conversion of farnesyl pyrophosphate to squalene Archives of Biochemistry and Biophysics. ,vol. 114, pp. 200- 215 ,(1966) , 10.1016/0003-9861(66)90322-5