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Advances in the chemistry of biotin

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Chemistry of Natural Compounds Aims and scope

Abstract

The review gives methods of synthesizing the biocatalyst biotin. The existing methods of obtaining biotin and its stereoisomers from dihaloalkanes, dicarboxylic acid esters, sugars, thiophene derivatives, etc., are discussed. The basic possibilities of the formation of biotin are considered.

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Literature cited

  1. V. M. Berezovskii, The Chemistry of the Vitamins [in Russian], Moscow (1973), pp. 433–458.

  2. D. B. Melville, A. W. Moyer, K. Hofmann, and V. de Vigneaud, J. Biol. Chem.,146, 487 (1942).

    CAS  Google Scholar 

  3. W. Traub, Nature (London),178, 649 (1956).

    Article  CAS  Google Scholar 

  4. J. Trotter and J. A. Hamilton, Biochemistry,5, 713 (1966).

    Article  CAS  Google Scholar 

  5. G. T. de Titta, J. W. Edmonds, W. Stallings, and J. Donohue, J. Am. Chem. Soc.,98, 1920 (1976).

    Article  Google Scholar 

  6. C.-S. Chen, R. Parthasrathy, and G. T. de Titta, J. Am. Chem. Soc.,98, 4983 (1976).

    Article  CAS  Google Scholar 

  7. T. Ogawa, T. Kawano, and M. Matsui, Carbohydr. Res.,57, C31 (1977).

  8. T. Tsuboi, C. Sekijo, and O. Shoji, Agr. Biol. Chem.,30, 1238 (1966).

    CAS  Google Scholar 

  9. A. Lezius, E. Ringelmann, and E. Lynen, Biochem. Z.,336, 294 (1963).

    Google Scholar 

  10. K. Dakshinamurti and S. P. Mistry, J. Biol. Chem.,238, 294 (1963).

    CAS  PubMed  Google Scholar 

  11. E. L. Tatum, J. Biol. Chem.,160, 455 (1945).

    CAS  PubMed  Google Scholar 

  12. M. A. Eisenberg, Adv. Enzymol.,38, 317 (1973).

    CAS  PubMed  Google Scholar 

  13. M. Černý, T. Trnka, P. Beran, and J. Pacák, Collect. Czech. Chem. Commun.,34, 3377 (1969).

    Article  Google Scholar 

  14. M. Černý, O. Julakoba, and J. Pacák, Collect. Czech. Chem. Commun.,39, 1391 (1974).

    Article  Google Scholar 

  15. M. L. Wolfrom, Y. L. Hung, P. Chakravarty, G. U. Yuen, and D. Horton, J. Org. Chem.,31, 2227 (1966).

    Article  CAS  Google Scholar 

  16. E. J. Corey, K. C. Nicolaou, R. D. Balanson, and Y. Machida, Synthesis, 590 (1975).

  17. H. Ohrui and S. Emoto, Tetrahedron Lett., 2765 (1975).

  18. E. Buchta and F. Andree, Chem. Ber.,92, 3111 (1959).

    Article  CAS  Google Scholar 

  19. R. J. Dimler, H. A. Davis, and G. E. Hilbert, J. Am. Chem. Soc.,88, 1377 (1946).

    Article  Google Scholar 

  20. Ya. V. Épshtein, O. P. Golova, and L. I. Durykina, Izv. Akad. Nauk SSSR, Ser. Khim., 1126 (1959).

  21. H. Ohrui, N. Sueda, and S. Emoto, Agric. Biol. Chem.,42, 865 (1978).

    CAS  Google Scholar 

  22. R. Duschinsky and L. A. Dolan, J. Am. Chem. Soc.,70, 657 (1948).

    Article  CAS  Google Scholar 

  23. R. Duschinsky and L. A. Dolan, J. Am. Chem. Soc.,67, 2079 (1945).

    Article  CAS  Google Scholar 

  24. S. I. Zav'yalov, M. P. Unanyan, G. V. Kondrat'eva, and V. V. Filippov, Izv. Akad. Nauk SSSR, Ser. Khim., 1792 (1967).

  25. R. U. Wiley, H. Wiley, and O. U. Borum, J. Am. Chem. Soc.,70, 2005 (1948).

    Article  CAS  Google Scholar 

  26. I. A. Rodionova, M. P. Unanyah, G. V. Kondrat'eva, S. I. Zav'yalov, and V. V. Filippov, Izv. Akad. Nauk SSSR, Ser. Khim., 660 (1970).

  27. T. Taguchi, Y. Sato, K. Watanabe, and T. Mukaiyama, Chem. Letters, 729 (1974).

  28. I. Isaka, K. Kubo, M. Takashima, and M. Murakami, Yakugaku Zasshi,88, 422 (1968).

    Article  CAS  Google Scholar 

  29. S. I. Zav'yalov, I. A. Rubtsov, L. L. Zheleznaya, A. B. Pavlova, and A. I. Rodionova, Izv. Akad. Nauk SSSR, Ser. Khim., 1679 (1973).

  30. S. I. Zav'yalov, I. A. Radionova, O. V. Dorofeeva, and L. L. Zheleznaya, Izv. Akad. Nauk SSSR, Ser. Khim., 2829 (1975).

  31. S. I. Zav'yalov, I. A. Rodionova, L. L. Zheleznaya, G. I. Bolestova, V. V. Filippova, Z. I. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1643 (1975).

  32. L. C. Cheney and J. R. Piening, J. Am. Chem. Soc.,67, 731 (1945).

    Article  CAS  Google Scholar 

  33. L. C. Cheney and J. R. Piening, J. Am. Chem. Soc.,66, 1040 (1944).

    Article  CAS  Google Scholar 

  34. E. Fischer and M. Bergmann, Ann. Chem.,398, 120 (1913).

    Article  Google Scholar 

  35. V. Prelog and S. Heimbach-Janász, Ber.,1702, 74 (1941).

    Google Scholar 

  36. P. Karrer, R. Keller, and E. Usteri, Helv. Chim. Acta,27, 237 (1944).

    Article  CAS  Google Scholar 

  37. H. Segawa and E. Imoto, Bull. Chem. Soc. Jpn.,38, 495 (1965).

    Article  CAS  Google Scholar 

  38. L. C. Cheney and D. Mich, U.S. Patent 2,502,422 (1950); Chem. Abstr.,44, 6440 (1950).

  39. J. Vasilevskis and W. Caldwell, U.S. Patent No. 4,130,712, cl. 548–303 (1978).

  40. S. Nishimura and E. Imoto, Bull. Soc. Chem. Jpn.,35, 432 (1962).

    Article  CAS  Google Scholar 

  41. B. P. Fabrichnyi, I. F. Shalavina, and Ya. L. Gol'dfarb, Dokl. Akad. Nauk SSSR,162, 120 (1965).

    CAS  PubMed  Google Scholar 

  42. B. P. Fabrichnyi, I. F. Shalavina, and Ya. L. Gol'dfarb, Zh. Obshch. Khim.,31, 1244 (1961).

    CAS  Google Scholar 

  43. P. Cagniat and A. Deluzarche, C. R.,222, 1301 (1946).

    Google Scholar 

  44. Ya. L. Gol'dfarb, S. Z. Taits, and L. I. Belen'kii, Zh. Obshch. Khim.,29, 3564 (1959).

    CAS  Google Scholar 

  45. P. N. Confalone, G. Pizzolato, and M. R. Uskoković, Helv. Chim., Acta,59, 1005 (1976).

    Article  CAS  Google Scholar 

  46. P. N. Confalone, G. Pizzolato, and M. R. Uskoković, J. Org. Chem.,42, 135 (1977).

    Article  CAS  Google Scholar 

  47. B. R. Baker, M. V. Querry, S. Bernstein, S. R. Safir, and Y. Subbarow, J. Org. Chem.,12, 167 (1947).

    Article  CAS  Google Scholar 

  48. J. Weinstock, J. Org. Chem.,26, 3511 (1961).

    Article  CAS  Google Scholar 

  49. P. N. Confalone, G. Pizzolato, and M. R. Uskoković, J. Org. Chem.,42, 1630 (1977).

    Article  CAS  Google Scholar 

  50. M. Marx, F. Marti, J. Reisdorff, R. Sandmeier, and S. Clark, J. Am. Chem. Soc.,99, 6554 (1977).

    Article  Google Scholar 

  51. K. Alder and H. von Brachel, Ann. Chem.,651, 141 (1962).

    Article  CAS  Google Scholar 

  52. C. A. Grob and H. Sprecher, Helv. Chim. Acta,35, 885 (1952).

    Article  CAS  Google Scholar 

  53. E. J. Corey, N. H. Andersen, R. M. Carlson, J. Paust, E. Vedejs, I. Vlattas, and R. K. Winter, J. Am. Chem. Soc.,90, 3245 (1968).

    Article  CAS  Google Scholar 

  54. J. P. Piper and T. P. Johnston, J. Org. Chem.,32, 1621 (1969).

    Google Scholar 

  55. M. Denis, C. Girard, and J. M. Conia, Synthesis, 549 (1972).

  56. O. Schnider, J. Bourquin, and A. Grussner, Helv. Chim. Acta,28, 510 (1945).

    Article  CAS  Google Scholar 

  57. A. Grussner, J. Bourquin, and O. Schnider, Helv. Chim. Acta,28, 517 (1945).

    Article  CAS  Google Scholar 

  58. A. Grussner, J. Bourquin, and O. Schnider, Helv. Chim. Acta,29, 770 (1946).

    Article  CAS  Google Scholar 

  59. H. Schmid, Helv. Chim. Acta,27, 128 (1944).

    Google Scholar 

  60. G. B. Brown, D. Armstrong, A. V. Moyer, W. P. Anslow, B. R. Baker, M. V. Querry, S. Bernstein, and S. R. Safir, J. Org. Chem.,12, 160 (1947).

    Article  CAS  Google Scholar 

  61. B. R. Baker, M. V. Querry, W. L. McEwen, S. Bernstein, S. R. Safir, L. Dorfmann, and Y. Subbarow, J. Org. Chem.,12, 186 (1947).

    Article  CAS  Google Scholar 

  62. B. R. Baker, W. L. McEwen, and V. N. Kinley, J. Org. Chem.,12, 322 (1947).

    Article  CAS  Google Scholar 

  63. S. A. Harris, D. E. Wolf, R. Mozingo, R. C. Anderson, G. E. Arth, N. R. Easton, D. Heyl, A. N. Wilson, and K. Folkers, J. Am. Chem. Soc.,66, 1756 (1944).

    Article  CAS  Google Scholar 

  64. S. A. Harris, D. E. Wolf, R. Mozingo, G. E. Arth, R. C. Anderson, N. R. Easton, and K. Folkers, J. Am. Chem. Soc.,67, 2096 (1945).

    Article  CAS  Google Scholar 

  65. S. D. Mikhno, V. M. Berezovskii, and N. A. Preobrazhenskii, Zh. Obshch. Khim.,32, 2829 (1962).

    CAS  Google Scholar 

  66. S. D. Mikhno, I. A. Solunina, V. A. Devyatkin, and V. M. Berezovskii, Zh. Analit. Khim.,22, 1419 (1967).

    CAS  Google Scholar 

  67. S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, S. I. Peretokina, V. I. Seredenko, I. G. Suchkova, Zh. I. Torosyan, and V. M. Berezovskii, Zh. Organ. Khim.,13, 175 (1977).

    CAS  Google Scholar 

  68. S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, T. I. Polyanskaya, I. M. Kustanovich, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., 897 (1972).

  69. S. D. Mikhno, T. I. Polyanskaya, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., 175 (1973).

  70. S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Suchkova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., 459 (1976).

  71. S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Suchkova, and V. M. Berezovskii, Zh. Org. Khim.,14, 1707 (1978).

    Google Scholar 

  72. P. N. Confalone, E. D. Lollar, G. Pizzolato, and M. R. Uskoković, J. Am. Chem. Soc.,100, 6291 (1978).

    Article  CAS  Google Scholar 

  73. L. F. Hatch and G. Bachmann, Chem. Ber.,97, 132 (1964).

    Article  CAS  Google Scholar 

  74. P. N. Confalone, G. Pizzolato, E. G. Baggiolini, D. Lollar, and M. R. Uskoković, J. Am. Chem. Soc.,97, 5936 (1975);99, 7020 (1977).

    Article  CAS  Google Scholar 

  75. M. W. Goldberg and L. H. Sternbach, U.S. Patent 2,489,236; Chem. Abstr.,45, 187 (1951).

  76. H. Ohrui and S. Emoto, Tetrahedron Lett., 2765 (1975).

  77. K. Freundenberg and A. Wolf, Ber.,60, 232 (1927).

    Google Scholar 

  78. E. Buchto and F. Andree, Chem. Ber.,92, 3111 (1959).

    Article  Google Scholar 

  79. M. W. Goldberg and L. H. Sternbach, U.S. Patent 2,489,232 (1949); Chem. Abstr.,45, 186 (1951).

  80. M. W. Goldberg and L. H. Sternbach, U.S. Patent 2,489,234 (1949); Chem. Abstr.,45, 186 (1951).

  81. M. W. Goldberg and L. H. Sternbach, U.S. Patent 2,489,235 (1949); Chem. Abstr.,45, 186 (1951).

  82. H. S. Rhinesmith, Org. Synth., Coll. II (1943), p. 177.

  83. W. Wenner, J. Org. Chem.,13, 26 (1948).

    Article  CAS  Google Scholar 

  84. I. D. Surmatis and N. J. Nutley, U.S. Patent 2,519,720, cl. 260–309 (1950).

  85. J. Isaka, K. Kubo, M. Takashima, and M. Murakami, Yakugaku Zasshi,88, 1062 (1968).

    Article  CAS  Google Scholar 

  86. K. Kogure, J. Yoshimura, H. Fukawa, and T. Shimizu, Agr. Biol. Chem.,40, 1658 (1976).

    Google Scholar 

  87. J. D. Surmatis and N. J. Nutley, U.S. Patent 2,759,682, cl. 260–309.7 (1951).

  88. I. Isaka, K. Kubo, M. Takashima, and M. Murukami, Yakugaku Zasshi,88, 1068 (1968).

    Article  CAS  Google Scholar 

  89. M. Gerecke, J. P. Zimmerman, and W. Aschwanden, Helv. Chim. Acta,53, 991 (1970).

    Article  CAS  Google Scholar 

  90. I. Isaka, K. Kubo, M. Takashima, and M. Murakami, Yakugaku Zasshi,88, 964 (1968).

    Article  CAS  Google Scholar 

  91. Y. Aoki, H. Suzuki, and H. Akiyama, Heterocycles,3, 67 (1975).

    Article  Google Scholar 

  92. S. Bory, M. J. Luche, B. Moreau, S. Lavielle, and A. Marquet, Tetrahedron Lett., 827 (1975).

  93. A. Marquet, Pure Appl. Chem.,49, 183 (1977).

    Article  CAS  Google Scholar 

  94. S. Lavielle, S. Bory, B. Moreau, M. J. Luche, and A. Marquet, J. Am. Chem. Soc.,100, 1558 (1978).

    Article  CAS  Google Scholar 

  95. C. R. Johnson and D. McCants, Jr., J. Am. Chem. Soc.,87, 1109 (1965).

    Article  CAS  Google Scholar 

  96. T. L. Ho and C. M. Wong, Synth. Commun.,3, 37 (1973).

    Article  CAS  Google Scholar 

  97. J. P. A. Castrillon and H. H. Szmant, J. Org. Chem.,30, 1338 (1965).

    Article  CAS  Google Scholar 

  98. G. F. Fild and W. Caldwell, GFR Patent 2,558,356, cl. CO7D495/04 (1976); Chem. Abstr.,86, 29, 809 (1977).

  99. G. F. Fild and W. Caldwell, U.S. Patent 4,054,740, cl. 548–303 (1977).

  100. M. Ternaki and S. Yoshinari, Japanese Patent 76,138,692 (1976); Chem. Abstr.,87, 53927 (1977).

  101. J. Vasilevskis, J. A. Gualtieri, S. D. Hutchings, R. C. West, J. W. Scot, D. R. Parrish, F. T. Bizzarro, and G. F. Fild, J. Am. Chem. Soc.,100, 7423 (1978).

    Article  CAS  Google Scholar 

  102. K. Folkers, R. Mozingo, and D. E. Wolf, U.S. Patent 2,442,681, cl. 260–309.7 (1948).

  103. K. Folkers, D. E. Wolf, and N. J. Rahway, U.S. Patent 2,441,141, cl. 260–309.7 (1948).

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All-Union Scientific-Research Vitamin Institute. Translated from Khimiya Pridodnykh Soedinenii, No. 4, pp. 445–477, July–August, 1980.

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Mikhno, D.D., Berezovskii, V.M. Advances in the chemistry of biotin. Chem Nat Compd 16, 313–338 (1980). https://doi.org/10.1007/BF00568361

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