Stoffwechsel der Sterine und Steroide (mit Ausnahme der Steroidhormone)

  • Hans Machleidt
  • Rudolf Tschesche

Zusammenfassung

Vor bereits 20 Jahren wurden die ersten Untersuchungen über die Biosynthese der Steroide mit isotopenmarkierten Verbindungen vorgenommen. Sonderhoff und Thomas ließen Hefe in Gegenwart von D3CCOOH wachsen und isolierten eine unverseifbare Fraktion, welche eine größere Menge an Deuterium als die isolierten Fettsäuren enthielt. Ähnliche Untersuchungen wurden später von Bloch und Rittenberg (1942) an Tieren durchgeführt. Das biosynthetisch erhaltene Cholesterin zeigte einen hohen Gehalt an Deuterium. Aus den Versuchen wurde deutlich, daß Acetat an der Biosynthese des Cholesterins beteiligt sein muß. Nachdem 13C- und 14C-Verbindungen zugänglich geworden waren, wurde diese Hypothese durch Einsatz von markierten Verbindungen stark ausgebaut. Rittenberg und Bloch (1945) gelang die Überführung von D3C—13COOH in das Cholesterin der Ratte, wobei sowohl D als auch 13C eingebaut wurden. Genauere Ergebnisse erhielten Little und Bloch durch Inkubation von Rattenleber-schnitten mit 14CH313COOH oder 13CH314COOH. Die Untersuchung des isolierten Cholesterins auf den Gehalt an 13C und 14C ergab ein Verhältnis von 1,27 Methyl: Carboxyl entsprechend 15 : 12, vorausgesetzt, alle 27 C-Atome des Cholesterins waren aus Acetat entstanden. Bei der Pyrolyse des in Cholesteryl-chlorid übergeführten Cholesterins entstanden ein C19-Kohlen wasserst off und iso-Octan.

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Literatur

  1. Adamson, L. F., and D. M. Greenberg: The significance of certain carboxylic acids as intermediates in the biosynthesis of cholesterol. Biochim. biophys. Acta 23, 472 (1957).PubMedCrossRefGoogle Scholar
  2. Agranoff, B. W., H. Eggerer, U. Henning and F. Lynen: Isopentenol pyrophosphate isomerase. J. Amer. chem. Soc. 81, 1254 (1959).CrossRefGoogle Scholar
  3. Alexander, G. J., A.M. Gold and E. Schwenk: The methyl group of methionine as a source of C-28 in ergosterol. J. Amer, chem Soc. 79, 2967 (1957).CrossRefGoogle Scholar
  4. Alexander, G. J., and E. Schwenk: Transfer of the methyl group of methionine to carbon-24 of ergosterol. J. Amer. chem. Soc. 79, 4554 (1957).CrossRefGoogle Scholar
  5. Amdur, B. H., H. Rilling and K. Bloch: The enzymatic conversion of mevalonic acid to squalene. J. Amer. chem. Soc. 79, 2646 (1957).CrossRefGoogle Scholar
  6. Anfinsen, C.B., and M. G. Horning: Enzymatic degradation of cholesterol side chain in cell-free preparations. J. Amer. chem. Soc. 75, 1511 (1953).CrossRefGoogle Scholar
  7. Anker, H. S.: Some aspects of the metabolism of pyruvic acid in the intact animal. J. biol. Chem. 176, 1337 (1948).PubMedGoogle Scholar
  8. Anker, H. S. and R. Raper: On the metabolic fate of pyruvamide and acetamide. J. biol. Chem. 176, 1353 (1948).PubMedGoogle Scholar
  9. Arigoni, D.: Zur Biogenese pentacyclischer Triterpene in einer höheren Pflanze. Experientia (Basel) 14, 153 (1958).CrossRefGoogle Scholar
  10. Bachhawat, B. K., W. G. Robinson and M. J. Coon: The enzymatic cleavage of /Miydroxy-β-methylglutarate coenzyme A to acetoacetate and acetyl coenzyme A. J. biol. Chem.216, 727 (1955).PubMedGoogle Scholar
  11. Bachhawat, B. K., and M. J. Coon: Enzymatic activation of carbon dioxyde. J. biol. Chem, 231, 625 (1958).PubMedGoogle Scholar
  12. Bergström, S., R.J. Bridgwater and U. Gloor: On the conversion of 3α,7α,12α-trihydroxy-coprostanic acid to cholic acids in rat liver homogenates. Acta chem. scand. 11, 836 (1957).CrossRefGoogle Scholar
  13. Bergström, S., and U. Gloor: Metabolism of bile acids in rat liver sclices and homogenates. Acta chem. scand 8, 1373 (1954).CrossRefGoogle Scholar
  14. Bergström, S., and U. Gloor: Distribution of the 7α-hydroxylating activity in rat liver homogenates. Acta chem. scand. 9, 1545 (1955).CrossRefGoogle Scholar
  15. Bergström, S., and S. Lindstedt: The formation of cholic acid from 3α,7α -dihydroxy-coprostane. Biochem. biophys. Acta 19, 556 (1956).PubMedCrossRefGoogle Scholar
  16. Bergström, S., and A. Norman: Metabolic products of cholesterol in bile and feces. Proc. Soc. exp. Biol. (N. Y.) 83, 71 (1953).CrossRefGoogle Scholar
  17. Bergström, S., K. Pääbo and J. A. Rumpf: Synthesis and metabolism of 3α,7α,12α-(4-14C)coprostane. Acta chem. scand. 8, 1109 (1954).Google Scholar
  18. Bergström, S., M. Rottenberger u. J. Sjövall: Über den Stoffwechsel der Cholsäure und Desoxychol-säure in der Ratte. Z. physiol. Chem. 295, 278 (1953).CrossRefGoogle Scholar
  19. Bergström, S., and J. Sjövall: Occurrence and metabolism of Chenodeoxycholic acid in the rat. Acta chem. scand. 8, 611 (1954).CrossRefGoogle Scholar
  20. Birch, A. J., R. J. English, R. A. Massy-Westropp and Herchel Smith: The origin of the terpenoid structures in mycelianamide and mycophenolic acid. Proc. chem. Soc. 1957, 323.Google Scholar
  21. Bloch, K.: Some aspects of the metabolism of leucin and valine. J. biol. Chem. 155, 255 (1944).Google Scholar
  22. Bloch, K.: The use of isotopes 4n hormone problems. The biological synthesis of cholesterol. Recent Progr. Hormone Res. 6, 111 (1951); New York: Academic Press Inc. Publ.Google Scholar
  23. Bloch, K.: Über die Herkunft des Kohlenstoff-Atoms 7 in Cholesterin. Ein Beitrag zur Kenntnis der Biosynthese der Steroide. Helv. chim. Acta 36, 1611 (1953).CrossRefGoogle Scholar
  24. Bloch, K.: The biological synthesis of cholesterol. Vitam. And Horm. Adv. in Res. and Appl. 15, 124 (1957).Google Scholar
  25. Bloch, K.: Biosynthesis of cholesterol. Hormones and atherosclerosis. Proc. Conference held in Brighton, Utah, March 1958. New York: Academic Press Inc. 1959.Google Scholar
  26. Bloch, K.: Vortrag auf dem IV. Intern. Kongreß für Biochemie in Wien, 1958.Google Scholar
  27. Bloch, K., B. N. Berg and D. Rittenberg: The biological conversion of cholesterol to cholic acid, J. biol. Chem. 149, 511 (1943).Google Scholar
  28. Bloch, K., E. Borek and D. Rittenberg: Synthesis of cholesterol in surviving liver. J. biol. Chem. 162, 441 (1946).PubMedGoogle Scholar
  29. Bloch, K., L. C. Clarke and I. Harary: Utilization of branched chain acids in cholesterol synthesis. J. biol. Chem. 211, 687 (1954).PubMedGoogle Scholar
  30. Bloch, K., and D. Rittenberg Zabin, and K. Bloch: Studies on the utilization of isovaleric acid in cholesterol synthesis. J. biol. Chem. 192, 267 (1951)PubMedGoogle Scholar
  31. Bloch, K., and D. Rittenberg Zabin, and K. Bloch: (2).: On the utilization of acetic acid for cholesterol formation. J. biol. chem. 145, 625 (1942).Google Scholar
  32. Bloch, K., and D. Rittenberg: Sources of acetic acid in the animal body. J. biol. Chem. 155, 243 (1944).Google Scholar
  33. Brady, R. O., and S. Gurin: The biosynthesis of radioactive fatty acids and cholesterol. J. biol. Chem. 186, 461 (1950).PubMedGoogle Scholar
  34. Brady, R. O., and S. Gurin: The synthesis of radioactive cholesterol and fatty acids in vitro. J. biol. Chem. 189, 371 (1951).PubMedGoogle Scholar
  35. Bridgwater, R. J., and S. Lindstedt: On the metabolism of 3 α,7α,12α-trihydroxycoprostanic acid in the rat. Acta chem. scand. 11, 409 (1957).CrossRefGoogle Scholar
  36. Byers, S.O., and M. W. Biggs: Cholic acid and cholesterol: Studies concerning possible intraconversion. Arch. Biochem. biophys. 39, 301 (1952).PubMedCrossRefGoogle Scholar
  37. Chaikoff, I. L., M. D. Siperstein, W. G. Dauben, H. L. Bradlow, J. I. Eastman, G. M. Tomkins, J. R. Meier, R. W. Chen, S. Hotta and P. A. Srere: 14C-cholesterol II. Oxydation of carbons 4 and 26 to carbondioxyde by the intact rat. J. biol. Chem. 194, 413 (1952).PubMedGoogle Scholar
  38. Clayton, R. B., and K. Bloch: Biological synthesis of lanosterol and agnosterol. J. biol. Chem. 218, 305 (1956);PubMedGoogle Scholar
  39. Clayton, R. B., and K. Bloch: The biological conversion of lanosterol to cholesterol. J. biol. Chem. 218, 319 (1956).PubMedGoogle Scholar
  40. Coon, M. J.: The metabolic fate of the isopropyl group of leucine. J. biol. Chem. 187, 71 (1950).PubMedGoogle Scholar
  41. Coon, M. J., and S. Gurin: Studies on the conversion of radioactive leucin to acetoacetate. J. biol. Chem. 180, 1159(1949).PubMedGoogle Scholar
  42. Cornforth, J. W., R. H. Cornforth, A. Pelter, M. G. Horning and G. Popják: Rearrangement of methyl groups in the enzymatic cyclization of squalen to lanosterol. Proc. chem. Soc. 1958, 112;Google Scholar
  43. Cornforth, J. W., R. H. Cornforth, A. Pelter, M. G. Horning and G. Popják: Rearrangement of methylgroups during enzymic cyclisation of squalen. Tetrahedron 5, 311 (1959).CrossRefGoogle Scholar
  44. Cornforth, J. W., R. H. Cornforth, G. Popják and I. Y. Gore: Studies on the biosynthesis of cholesterol V. Biosynthesis of Squalen from DL-3-Hydroxy-3-methyl-(2-14C)-pentano-5-lacton. Biochem. J. 69, 146 (1958).PubMedGoogle Scholar
  45. Cornforth, J. W., I. Y. Gore and G. Popják: Studies on the biosynthesis of cholesterol IV. Degradation of rings C and D .Biochem. J. 65, 94 (1957).PubMedGoogle Scholar
  46. Cornforth, J. W., G. D. Hunter and G. Popják: Studies in cholesterol biosynthesis. A new chemical degradation of cholesterol. Biochem. J. 54, 590 (1953).PubMedGoogle Scholar
  47. Cornforth, J. W., G. D. Hunter and G. Popják: Studies of cholesterol biosynthesis II. Distribution of acetate carbon in the ring structure. Biochem. J. 54, 597 (1953).PubMedGoogle Scholar
  48. Cornforth, J. W., and G. Popják: Studies on the biosynthesis of cholesterol III. Distribution of 14C-squalen biosynthesized from (Me-14C)-acetate. Biochem. J. 58, 403 (1954).PubMedGoogle Scholar
  49. Curran, G. L.: Utilization of acetoacetic acid in cholesterol synthesis by surviving rat liver. J. biol. Chem 191, 775 (1951).PubMedGoogle Scholar
  50. Curran, G. L. and D. Rittenberg: The role of ethyl alcohol in the biological synthesis of cholesterol. J. biol. Chem. 190, 17 (1951).PubMedGoogle Scholar
  51. Danielsson, H., and K. Bloch: On the origin of C-28in ergosterol. J. Amer. chem. Soc. 79, 500 (1957).CrossRefGoogle Scholar
  52. Dauben, W. G., Y. Ban and J. H. Richards: The biosynthesis of the triterpen eburicoic acid. The utilization of methyl-labelled acetate. J. Amer. chem. Soc. 79, 968 (1957).CrossRefGoogle Scholar
  53. Dauben, W. G., and T. W. Hutton: The biosynthesis of steroids and triterpenes. The origin of carbons 11 and 12 of ergosterol. J. Amer. chem. Soc. 78, 2647 (1956).CrossRefGoogle Scholar
  54. Dauben, W. G., and J. H. Richards: The biosynthesis of triterpen eburicoic acid. J. Amer. chem. Soc. 78, 5329 (1956).CrossRefGoogle Scholar
  55. Dauben, W. G., and K. H. Takemura: A study of the mechanism of conversion of acetate to cholesterol via squalen. J. Amer. chem. Soc. 75, 6302 (1953).CrossRefGoogle Scholar
  56. Dekker, E. E., M. J. Schlesinger and M. J. Coon: β-hydroxy-β-methyl-glutaryl coenzyme A deacylase. J. biol. Chem. 233, 434 (1958).PubMedGoogle Scholar
  57. DeWaard, A., A. H. Phillips and K. Bloch: Mechanism of the formation of isopentenyl pyrophosphate. J. Amer. chem. Soc. 81, 2913 (1959).CrossRefGoogle Scholar
  58. Dituri, F., F. A. Cobey, J. U. B. Warms and S. Gurin: Terpenoid intermediates in the biosynthesis of cholesterol. J. biol. Chem. 221, 181 (1956).PubMedGoogle Scholar
  59. Dituri, F., J. L. Rabino Witz and S. Gurin: The biosynthesis of squalen from mevalonic acid. J. Amer. chem. Soc. 79, 2650 (1957).CrossRefGoogle Scholar
  60. Dituri, F., J. L. Rabino Witz, R. P. Hullins and S. Gurin: Precursors of squalene and cholesterol. J. biol. Chem. 229, 825 (1957).PubMedGoogle Scholar
  61. Eggerer, H., F. Lynen, E. Rauenbusch u. I. Kessel: Zur Biosynthese der Polyisoprenoide. I. Darstellung von β-Hydroxy-α-methyl-glutaraldehydsäure. Liebigs Ann. Chem. 608, 71 (1957).CrossRefGoogle Scholar
  62. Ekdahl, P. H., and J. Sjövall: Metabolism of desoxycholic acid in the rabbit. Acta physiol. scand. 34, 287 (1955).PubMedCrossRefGoogle Scholar
  63. Elliott, W. H.: Enzymatic activation of cholic acid involving coenzyme A. Biochim. biophys. Acta 17, 440 (1955).CrossRefGoogle Scholar
  64. Eschenmoser, A., L. Ruzicka, O. Jeger u. D. Arigoni: Zur Kenntnis der Triterpene 190.Google Scholar
  65. Mitteilg. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helv. chim. Acta 38, 1890 (1955).CrossRefGoogle Scholar
  66. Gautschi, F., and K. Bloch: On the structure of an intermediate in the biological demethylation of lanosterol. J. Amer. chem. Soc. 79, 684 (1957).CrossRefGoogle Scholar
  67. Gautschi, F., and K. Bloch: Synthesis of Isomeric 4,4-dimethyl-cholestenols and identification of a lanosterol metabolite. J. biol. Chem. 233, 1343 (1958).PubMedGoogle Scholar
  68. Gloor, U.: Konjugation und Oxydation von Gallensäure in Rattenleberhomogenaten. Helv. chim. Acta 37, 1927 (1954).CrossRefGoogle Scholar
  69. Gould, R. G., and G. Popjak: Biosynthesis of cholesterol in vivo and in vitro from DL-β-hydroxy-β-methyl-(2-14C)-valerolactone. Biochem. J. 66, 51 P (1957).Google Scholar
  70. Gray, R. I., P. Adams and H. Hauptman: The utilization of the branched chain of isobutyric acid studied with 14C. Experientia (Basel) 6, 430 (1950).CrossRefGoogle Scholar
  71. Hilz, H., J. Knappe, E. Ringelmann u. F. Lynen: Methylglutaconase, eine neue Hydratase, die am Stoffwechsel verzweigter Carbonsäuren beteiligt ist. Biochem. Z. 329, 476 (1958).PubMedGoogle Scholar
  72. Horning, M. G.: Studies in the enzymatic degradation of the cholesterol side chain II. Requirements of the mitochondrial system. Arch. Biochem. biophys. 71, 266 (1957).PubMedCrossRefGoogle Scholar
  73. Hunter, G. D., and G. Popjak: A new method for degradation of n-carboxylic acid. Biochem. J. 50, 163 (1951).PubMedGoogle Scholar
  74. Isler, O., R. Rüegg, J. Würsch, K. F. Gey u. A. Pletscher: Zur Biosynthese des Cholesterins aus β,δ-Dihydroxy-β-methyl-n-valeriansäure. Helv. chim. Acta 40, 2369 (1957).CrossRefGoogle Scholar
  75. Johnson, J. D., and K. Bloch: In vitro conversion of zymosterol and dihydrozymosterol to cholesterol. J. Amer. chem. Soc. 79, 1145 (1957).CrossRefGoogle Scholar
  76. Kandutsch, A. A., and A. E. Russell: The identification of 4α-methyl-Δ8-cholesten-3β-ol, a new sterol from a preputial gland tumor. J. Amer. chem. Soc. 81, 4114 (1959).CrossRefGoogle Scholar
  77. Langdon, R. G., and K. Bloch: The biosynthesis of squalen. J. biol. Chem 200, 129 (1953).PubMedGoogle Scholar
  78. Langdon, R. G., and K. Bloch: The utilization of squalen in the biosynthesis of cholesterol. J. biol. Chem. 200, 135 (1953).PubMedGoogle Scholar
  79. Lindstedt, S.: The formation of bile acids from 7a-hydroxycholesterol. Acta chem. scand. 11, 417 (1957).CrossRefGoogle Scholar
  80. Lindstedt, S., and A. Norman: On the excretion of bile acid derivatives in faeces of rats fad cholic acid-24-14C and chenodesoxy cholic acid-24-14C. Acta physiol. scand. 34, 1 (1955).PubMedCrossRefGoogle Scholar
  81. Lindstedt, S., and A. Norman: On the metabolism of taurin conjugated 3α,7α,12α-trihydroxycoprostanic acid in the rat. Acta chem. scand. 11, 414 (1957).CrossRefGoogle Scholar
  82. Little, H. N., and K. Bloch: Studies on the utilization of acetic acid for the biological synthesis of cholesterol. J. biol. Chem. 183, 33 (1950).Google Scholar
  83. Lynen, F.: Coenzyme A, ein Bindeglied zwischen energieliefernden und verbrauchenden Reaktionen des Zellstoffwechsels. Klin. Wschr. 35, 213 (1957).PubMedCrossRefGoogle Scholar
  84. Lynen, F., U. Henning, G. Bublitz, B. Sörbo u. L. Kröplin-Rueff: Der chemische Mechanismus der Acetessigsäurebildung in der Leber. Biochem. Z. 330, 269 (1958).PubMedGoogle Scholar
  85. Lynen, F.: Verzweigte Carbonsäuren als Baustoffe der Polyisoprenoide. Proc. int. symposium of enzyme chemistry, Tokyo and Kyoto 1958.Google Scholar
  86. Lynen, F., H. Eggerer, U. Henning u. I. Kessel: Farnesyl-pyrophosphat und 3-Methyl-Δ3-butenyl-1-pyrophosphat, die biologischen Vorstufen des Squalens. Angew. Chem. 70, 738 (1958).CrossRefGoogle Scholar
  87. Matschiner, J. T., R. Richter, W. H. Elliott and E. A. Doisy jr.: Metabolic studies of carboxyl-labelled14C-desoxycholic acid. Fed. Proc. 13, 261 (1954).Google Scholar
  88. Maudgal, R. K., T. T. Tchen and K. Bloch: 1,2-methyl shifts in the cyclization of squalene to lanosterol. J. Amer. chem. Soc. 80, 2589 (1958).CrossRefGoogle Scholar
  89. Norman, A.: Influence of chemotherapeutics on the metabolism of bile acids in the intestine of rats. Acta physiol. scand. 33, 99 (1955).PubMedCrossRefGoogle Scholar
  90. Ogilvie, J. W. jr., and R. G. Langdon: The enzymatic conversion of mevalonic acid-2-14C to an olefinic acid. J. Amer. chem. Soc. 81, 756 (1959).CrossRefGoogle Scholar
  91. Olson, J. A. jr., M. Lindberg and K. Bloch: On the demethylation of lanosterol to cholesterol. J. biol. Chem. 226, 941 (1957).PubMedGoogle Scholar
  92. Ottke, R. C., E. L. Tatum, I. Zabin and K. Bloch: Isotopic acetate and isovalerate in the synthesis of ergosterol by neurospora. J. biol. Chem. 189, 429 (1951).PubMedGoogle Scholar
  93. Parks, L. W.: S-Adenosylmethionine and ergosterol synthesis. J. Amer. chem. Soc. 80, 2023 (1958).CrossRefGoogle Scholar
  94. Popjak, G.: Biosynthesis of squalen and cholesterol in vitro from acetate- 1-14C. Arch. Biochem. Biophys. 48, 102 (1954).PubMedCrossRefGoogle Scholar
  95. Popjak, G., L. Gosselin, I. Y. Gore and R. G. Gould: Studies in the biosynthesis of cholesterol VI. Coenzyme requirements of liver enzymes for synthesis of squalen and of sterol from DL-3-hydroxy-3-methyl-(2-14C)-pentano-5-lactone. Biochem. J. 69, 238 (1958).PubMedGoogle Scholar
  96. Popjak, G., M. Horning, N. L. R. Bucher and R. H. Cornforth: The formation of terpenoid acids from mevalonic acid in liver enzyme preparations and their relation to sterol biosynthesis. Biochem. J. 72, 34P (1959).Google Scholar
  97. Price, T. D., and D. Rittenberg: The metabolism of acetone. J. biol. Chem. 185, 449 (1950).PubMedGoogle Scholar
  98. Rabinowitz, J. L.: The biosynthesis of radioactive β-hydroxy-β-methyl-glutaric acid in rat liver. J. Amer. chem. Soc. 77, 1295 (1955).CrossRefGoogle Scholar
  99. Popjak, G., and S. Gurin: Biosynthesis of cholesterol-and β-hydroxy-β-methyl-glutaric acid by extracts of liver. J. biol. Chem. 208, 307 (1954).Google Scholar
  100. Popjak, G., and Gurin: The biosynthesis of radioactive cholesterol, β-methylglutaconic acid and β-methylcrotonic acid by aequeous extracts of liber. J. Amer. chem. Soc. 76, 5168 (1954).CrossRefGoogle Scholar
  101. Rittenberg, D., and K. Bloch: The utilization of acetic acid for the synthesis of fatty acids. 160, 417 (1945).Google Scholar
  102. Robinson, R.: Structure of cholesterol. J. Soc. ehem. Ind. 53, 1062 (1934).CrossRefGoogle Scholar
  103. Rudney, H.: The synthesis of /Miydroxy-β-methyl-glutaric acid by rat liver homogenates. J. Amer. ehem. Soc. 76, 2595 (1954).CrossRefGoogle Scholar
  104. Rudney, H.: Biosynthesis of /Miydroxy-β-methyl-glutarie acid (HMG) Fed. Proc. 15, 342 (1956).Google Scholar
  105. Rudney, H., I. F. Dürr and J. J. Ferguson: Formation of mevalonic acid from β-hydroxy-β-methyl-glutaryl-coenzyme A.Division of biol. Chem.Amer. chem. Soc. Abstracts of papers. April 5–10, 1959.Google Scholar
  106. Rudney, H., and J. J. Ferguson: The biosynthesis of β-hydroxy-β-methylglutaryl coenzyme A. J. Amer, chem: Soc. 79, 5580 (1957).CrossRefGoogle Scholar
  107. Ruzicka, L.: The isoprene rule and the biogenesis of terpenic compounds. Experientia (Basel) 9, 357 (1953).CrossRefGoogle Scholar
  108. Schneider, P. B., R. B. Clayton and K. Bloch: Synthesis of lanosterol in vivo. J. biol. Chem. 224, 175 (1957).PubMedGoogle Scholar
  109. Schwenk, E., G. J. Alexander, C. A. Fish and T. H. Stoudt: Biosynthesis of substances which accompany cholesterol. Fed. Proc. 14, 725 (1955).Google Scholar
  110. Shunk, C H., B. O. Linn, J. W. Huff, J. L. Gilfillan, H. R. Skeggs and K. Folkers: Resolution of DL-mevalonic acid and the synthesis and biological activities of DL-3-hydroxy-3-methylglutaraldehydic acid. J. Amer. chem. Soc. 79, 3294 (1957).CrossRefGoogle Scholar
  111. Siperstein, M. D.: Enzymatic synthesis of bile salts. Fed. Proc. 14, 281 (1955).Google Scholar
  112. Siperstein, M. D., and I. L. Chaikoff: 14C-cholesterol III. Excretion of carbons 4 and 26 in feces, urine and bile. J. biol. Chem. 198, 93 (1952).PubMedGoogle Scholar
  113. Siperstein, M. D., and A. W. Murray: Enzymatic synthesis of cholyl CoA and Taurocholic acid. Science 123, 377 (1956).PubMedCrossRefGoogle Scholar
  114. Siperstein, M. D., M. E. Yayko, I. L. Chaikoff and W. G. Dauben: Nature of the metabolic products of 14C-cholesterol excreted in bile and feces. Proc. Soc. exp. Biol. (N. Y.) 81, 720 (1952).CrossRefGoogle Scholar
  115. Sonderhoff, R., u. H. Thomas: Die enzymatische Dehydrierung der Trideutero-Essigsäure. Liebigs Ann. Chem. 530, 195 (1937).CrossRefGoogle Scholar
  116. Staple, E., and S. Gurin: The incorporation of radioactive acetate into biliary cholesterol and cholic acid. Biochim. biophys. Acta 15, 372 (1954).Google Scholar
  117. Stockes, W. M., W. A. Fish and F. C Hickey: Metabolism of cholesterol in the chick embryo II. Isolation and the chemical nature of two compagnion sterols. J. biol. Chem. 220, 415 (1956).Google Scholar
  118. Tavormina, P. A., and M. H. Gibbs: The metabolism of β,δ-dihydroxy-β-methyl-valeric acid by liver homogenates. J. Amer. chem. Soc. 78, 6210 (1956).CrossRefGoogle Scholar
  119. Tavormina, P. A., and M. H. Gibbs, and J. W. Huff: The utilization of β-hydroxy-β-methyl-δ-valerolactone in the cholesterol biosynthesis. J. Amer. chem. Soc. 78, 4498 (1956).CrossRefGoogle Scholar
  120. Tchen, T. T.: On the formation of a phosphorylates derivative of mevalonic acid. J. Amer. chem. Soc. 79, 6344 (1957).CrossRefGoogle Scholar
  121. Tchen, T. T., and K. Bloch: Vitamins and hormones. Advanc. in Res. and Appl. 15, 125 (1957).Google Scholar
  122. Tchen, T. T., and K. Bloch: On the conversion of squalen to lanosterol in vitro. J. biol. Chem. 226, 921 (1957).PubMedGoogle Scholar
  123. Tchen, T. T., and K. Bloch: On the mechanism of enzymatic cyclization of squalen. J. biol. Chem. 226, 931 (1957).PubMedGoogle Scholar
  124. Tryding, N., and G. Gvestöö: Metabolism of 2-methylstearic acid in the rat. Acta chem. scand. 11, 427 (1957).CrossRefGoogle Scholar
  125. Tryding, N., and s: On, the metabolism of bishomocholic, homocholic and norcholic acids in the rat. Ark. Kemi 11, 137 (1957).Google Scholar
  126. Voser, W., M. U. Mijovik, H. Heusser, O. Jeger u. L. Ruzicka: Über die Konstitution des Lanostadienols (Lanosterins) und seine Zugehörigkeit zu den Steroiden. Helv. chim. Acta 35, 2414 (1952).CrossRefGoogle Scholar
  127. Wolf, D. E., C. H. Hofman, P. E. Aldrich, H. R. Skeggs, L. D. Wright and K. Folkers: β-hydroxy-β-methyl-δ-valerolactone (divalonic acid). A new biological factor. J. Amer. chem. Soc. 78, 4499 (1956).CrossRefGoogle Scholar
  128. Wolf, D. E., C. H. Hofman, P. E. Aldrich, H. R. Skeggs, Determination of structure of β,δ-dihydroxy-β-methyl-valeric acid. J. Amer. chem. Soc. 79, 1486 (1957).CrossRefGoogle Scholar
  129. Woodward, R. B., and K. Bloch: The cyclization of squalen in cholesterol synthesis. J. Amer. chem. Soc. 75, 2023 (1953).CrossRefGoogle Scholar
  130. Wright, L. D., M. Cleland and J. S. Norton: Mevaldic acid in the biosynthesis of mevalonic acid. J. Amer. chem. Soc. 79, 6572 (1957).CrossRefGoogle Scholar
  131. Wüersch, J., R. L. Huang and K. Bloch: The origin of the Isooctyl side chain of cholesterol. J. biol. Chem. 195, 439 (1952).PubMedGoogle Scholar
  132. Zabin, I., and W. F. Barker: The conversion of cholesterol and acetate to cholic acid. J. biol. Chem 205, 633 (1953).PubMedGoogle Scholar
  133. Zabin, I., and K. Bloch: The utilization of isovaleric acid for the synthesis of cholesterol. J. biol. Chem. 185, 131 (1950).PubMedGoogle Scholar
  134. Zabin, I., and K. Bloch: The utilization of butyric acid for the synthesis of cholesterol and fatty acids. J. biol. Chem. 192, 261 (1951) (1).PubMedGoogle Scholar
  135. Zabin, I., and K. Bloch: Studies on the utilization of isovaleric acid in cholesterol synthesis. J. biol. Chem. 192, 267 (1951) (2).PubMedGoogle Scholar

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© Springer-Verlag Berlin Heidelberg 1961

Authors and Affiliations

  • Hans Machleidt
  • Rudolf Tschesche

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