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Resolution of Amino Acids

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Abstract

Most of the purposes for which amino acids are needed call for resolved samples of the chiral amino acids. These are available either (i) from a natural source (ii) through asymmetric synthesis, or (iii) through resolution of a DL-amino acid obtained by synthesis. There are major limitations of supply involved in the dependence on a natural source for uncommon amino acids, and asymmetric synthesis has yet to be developed into a reliable general process. In any case, synthesis followed by resolution is usually a more attractive proposition for the supply of novel or uncommon amino acids in required amounts since, even if the other methods are at first sight more convenient, these also require separation stages and checks of optical purity. Assignment of absolute configuration is also a necessary step in the resolution of novel DL-amino acids; spectroscopic methods used for configurational assignments are discussed in Chapter 19.

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References

  1. Jacques, J., Collet, A. and Wilen, S.H. (1981)Enantiomers, Racemates, and Resolutions, Wiley, New York.

    Google Scholar 

  2. Jacques, J., Collet, A. and Wilen, S.H. (1977)Tetrahedron,33, 2725.

    Article  Google Scholar 

  3. Dalgleish, C.E. (1952)J. Chem. Soc,137, 3940.

    Article  Google Scholar 

  4. Handes, L.V., Kido, R. and Schmaeler, M. (1974)Prep. Biochem,4, 47.

    Article  Google Scholar 

  5. Stewart, K.K. and Doherty, R.F. (1973)Proc. Nat. Acad. Sci. USA,70, 2850.

    Article  Google Scholar 

  6. El Din Awad, A.M. and El Din Awad, O.M. (1974)J. Chromatogr,93, 393.

    Article  Google Scholar 

  7. Davankov, V.A., Rogozhin, S.V. and Semechkin, A.V. (1974)J. Chromatogr,91, 493.

    Article  Google Scholar 

  8. Zolotarev, Yu.A., Myasoedov, N.N., Penkina, V.I.,et al(1981)J. Chromatogr,207, 231.

    Article  Google Scholar 

  9. Kurganov, A.A. and Davankov, V.A. (1981)J. Chromatogr,218, 559.

    Article  Google Scholar 

  10. Tapuhi, Y., Miller, N. and Karger, B.L. (1981)J. Chromatogr,205, 325.

    Article  Google Scholar 

  11. Sousa, L.R., Hoffman, D.H., Kaplan, L. and Cram, D.J. (1974)J. Am. Chem. Soc,96, 7100.

    Article  Google Scholar 

  12. Helgeson, R.C., Timko, J.M., Moreau, P.,et al(1974)J. Am. Chem. Soc,96, 6762.

    Article  Google Scholar 

  13. Cram, D.J. and Cram, J. M. (1974)Science,183, 803.

    Article  Google Scholar 

  14. Helgeson, R.C., Koga, K., Timko, J.M. and Cram, D.J. (1973)J. Am. Chem. Soc,95, 3021.

    Article  Google Scholar 

  15. Deber, C.M. and Blout, E.R. (1974)J. Am. Chem. Soc,96, 7566.

    Article  Google Scholar 

  16. Howard, P.Y. and Parr, W. (1974)Chromatographia, 7, 283.

    Article  Google Scholar 

  17. Gil-Av, E. and Feibush, B. (1967)Tetrahedron Lett., 3345.

    Google Scholar 

  18. Iwase, H. and Murai, A. (1974)Chem. Pharm. Bull., Japan,22, 1455.

    Google Scholar 

  19. Nambara, T., Goto, J., Toguchi, K. and Iwata, T. (1974)J. Chromatogr,100, 180.

    Article  Google Scholar 

  20. Barth, T. and Maskova, H. (1971)Coll. Czech. Chem. Commun,36, 2398.

    Google Scholar 

  21. Greenstein, J.P. and Winitz, M. (1961)Chemistry of the Amino Acids, Wiley, New York.

    Google Scholar 

  22. Baker, C.G., Fu, Shou-Cheng J., Birnbaum, S.M.,et al(1952)J. Am. Chem. Soc,74, 4701.

    Article  Google Scholar 

  23. Fu, Shou-Cheng J. and Birnbaum, S.M. (1953)J. Am. Chem. Soc,75, 918.

    Article  Google Scholar 

  24. Baldwin, J.E., Kruse, L.I. and Cha, J.-K. (1981)J. Am. Chem. Soc,103, 942.

    Article  Google Scholar 

  25. Kelley-Schierlein, W. and Joos, B. (1980)Helv. Chim. Acta,63, 250.

    Article  Google Scholar 

  26. Keith, D.D., Tortora, J.A. and Yang, R. (1978)J. Org. Chem,43, 3711.

    Article  Google Scholar 

  27. Kuhlmann, W., Halwachs, W. and Schnegerl, K. (1980)Chem.-ing. Tech,52, 607.

    Article  Google Scholar 

  28. Sugie, M. and Suzuki, H. (1980)Agric. Biol. Chem,44, 1089.

    Article  Google Scholar 

  29. Berger, A., Smolarsky, M., Kurn, N. and Bosshard, H.R. (1973)J. Org. Chem,38, 457.

    Article  Google Scholar 

  30. Bosshard, H.R. and Berger, A. (1973)Helv. Chem. Acta,56, 1838.

    Article  Google Scholar 

  31. Fauchere, J. L. and Petermann, C. (1981)Int. J. Pept. Protein Res,18, 249.

    Article  Google Scholar 

  32. Matta, M.S., Kelley, J.A., Tietz, A.J. and Rohde, M.F. (1974)J. Org. Chem,39, 2291.

    Article  Google Scholar 

  33. Tong, J.H., Petitclerc, C., D’Iorio, A. and Benoiton, N.L. (1971)Canad. J. Biochem,49, 877.

    Google Scholar 

  34. Anantharamaiah, G.M. and Roeske, R.W. (1982)Tetrahedron Lett,23, 3335.

    Article  Google Scholar 

  35. Bernasconi, S., Corbella, A., Garibaldi, P. and Jommi, G. (1977)Gazzetta,107, 95.

    Google Scholar 

  36. Gerig, J.T. and Klinkenborg, J.C. (1980)J. Am. Chem. Soc,102, 4267.

    Article  Google Scholar 

  37. Abernethy, J.L., Albano, E. and Comyns, J. (1971)J. Org. Chem,36, 1580.

    Article  Google Scholar 

  38. Abernethy, J.L., Howell, F.G., Ledesma, A., et al. (1975)Tetrahedron,31, 2659.

    Article  Google Scholar 

  39. Mohrig, J.R. and Shapiro, S.M. (1976)J. Chem. Educ,53, 586.

    Article  Google Scholar 

  40. Arendt, A., Kolodziejczyk, A., Sokolowska, T. and Szufler, E. (1974)Rocz. Chem,48, 635.

    Google Scholar 

  41. Turk, J., Panse, G.T. and Marshall, G.T. (1975)J. Org. Chem,40, 953.

    Article  Google Scholar 

  42. Sarda, N., Grouiller, A. and Pacheco, H. (1976)Tetrahedron Lett., 271.

    Google Scholar 

  43. Purdie, J.E., Demayo, R.E., Seely, J.H. and Benoiton, N.L. (1972)Biochim. Biophys. Acta,268, 523.

    Google Scholar 

  44. Monsan, P. and Duran, G. (1978)Biochim. Biophys. Acta,523, 477.

    Google Scholar 

  45. Coletti-Previero, M.A. and Axelrud-Cavadore, C. (1975)Biochem. Biophys. Res. Commun,62, 844.

    Article  Google Scholar 

  46. Wilschowitz, L., H6fle, G., Steglich, W. and Barrett, G.C. (1970)Tetrahedron Lett., 169.

    Google Scholar 

  47. Barrett, G.C. (1980)Tetrahedron,36, 2083.

    Article  Google Scholar 

  48. Fessenden, R.A. and Fessenden, J.S. (1979)Organic Chemistry, Wadsworth, Boston, Mass, p. 867.

    Google Scholar 

  49. Casey, D.L., Digenis, G.A., Wesner, D.A.,et al(1981)Int. J. Appl. Radiat. Isot,32, 325.

    Article  Google Scholar 

  50. Yamada, H., Shimizu, S., Shimiada, H.,et al(1980)Biochimie,62, 395.

    Article  Google Scholar 

  51. Shimizu, S., Shimada, H., Takahashi, S.,et al(1980)Agric. Biol. Chem,44, 2233.

    Article  Google Scholar 

  52. Sano, K., Yokozeki, K., Eguchi, C.,et al(1977)Agric. Biol. Chem,41, 819.

    Article  Google Scholar 

  53. Fukumura, T. (1977)Agric. Biol. Chem,41, 1321, 1327.

    Article  Google Scholar 

  54. Arnaud, A., Gaizy, P. and Janageas, J.-C. (1980)Bull. Soc. Chim. France, Part 2, 87.

    Google Scholar 

  55. Chang, Y.-F. and Massey, S.C. (1980)Prep. Biochem,10, 215.

    Article  Google Scholar 

  56. Clark, J.C., Phillipps, G.H. and Steer, M.R. (1976)J. Chem. Soc., Perkin 1, 475.

    Article  Google Scholar 

  57. Sifniades, S., Boyle, W.J. and Van Peppen, J.F. (1976)J. Am. Chem. Soc,98, 3738.

    Article  Google Scholar 

  58. Boyle, W.J., Sifniades, S. and Van Peppen, J.F. (1979)J. Org. Chem,44, 4841.

    Article  Google Scholar 

  59. Yamada, S., Hongo, C. and Chibata, O. (1980)Chem. and Ind., 539.

    Google Scholar 

  60. Yamada, S., Yamamoto, M. and Chibata, I. (1975)J. Org. Chem,40, 3360.

    Article  Google Scholar 

  61. Hongo, C., Shibazaki, M., Yamada, S. and Chibata, I. (1976)J. Agric. Food Chem,24, 903.

    Article  Google Scholar 

  62. Felder, E. and Pitre, D. (1977)Farmaco Ed. Sci,32, 123.

    Google Scholar 

  63. Yamada, S., Hongo, C., Yamamoto, M. and Chibata, I. (1976) Agric. Biol. Chem., 40,1425(Chem. Abs., 1965, 62 13233

    Google Scholar 

  64. Secor, R.M. (1963)Chem. Rev,63, 297.

    Article  Google Scholar 

  65. Kaneko, T., Izumi, Y., Chibata, I. and Itoh, T. (eds) (1974)Synthetic Production and Utilization of Amino Acids, Wiley, New York.

    Google Scholar 

  66. Watanabe, T. and Noyori, G. (1967)J. Chem. Soc. Japan, Ind. Chem. Sect,70, 2164, 2167, 2170, 2174.

    Google Scholar 

  67. Watanabe, T. and Noyori, G. (1969)J. Chem. Soc. Japan, I nd. Chem. Sect,72, 1080, 1083.

    Google Scholar 

  68. Chibata, I., Yamada, S., Yamamoto, M. and Wada, M. (1968)Experientia,24, 638.

    Article  Google Scholar 

  69. Yamada, S., Yamamoto, M. and Chibata, I. (1973)J. Org. Chem,38, 4408.

    Article  Google Scholar 

  70. Yamada, S., Hongo, C. and Chibata, I. (1978)Agric. Biol. Chem,42, 1521.

    Article  Google Scholar 

  71. Hongo, C., Yamada, S. and Chibata, I. (1981)Bull. Chem. Soc. Japan,54, 1905, 1911.

    Article  Google Scholar 

  72. Hongo, C., Yamada, S. and Chibata, I. (1981) Bull. Chem. Soc. Japan, 54, 1905, 1911

    Google Scholar 

  73. Yamamoto, H., Hasegawa, H. and Harano, Y. (1981)J. Chem. Eng. Japan.,14, 59.

    Article  Google Scholar 

  74. Addadi, L. and Lahav, M. (1978)J. Am. Chem. Soc,100, 2831.

    Article  Google Scholar 

  75. Addadi, L. and Lahav, M. (1979)Pure Appl. Chem,51, 1269.

    Article  Google Scholar 

  76. Addadi, L., Gati, E. and Lahav, M. (1981)J. Am. Chem. Soc,103, 1251.

    Article  Google Scholar 

  77. Yamskov, I.A., Berezin, B.B. and Davankov, V.A. (1980)Makromol. Chem., Rapid Commun,1, 125.

    Article  Google Scholar 

  78. Garay, A.S. (1968)Nature,219, 338.

    Article  Google Scholar 

  79. Garay, A.S. (1978)Nature,271, 186.

    Article  Google Scholar 

  80. Norden, B. (1977)Nature,266, 567.

    Article  Google Scholar 

  81. Flores, J.J., Bonner, W.A. and Massey, G.A. (1977)J. Am. Chem. Soc,99, 3622.

    Article  Google Scholar 

  82. Darge, W., Laczo, I. and Thiemann, W. (1976)Nature,261, 522.

    Article  Google Scholar 

  83. Darge, W., Laczo, I. and Thiemann, W. (1979)Nature,281, 151.

    Article  Google Scholar 

  84. Bonner, W.A., Blair, N.E. and Flores, J.J. (1979)Nature,281, 150.

    Article  Google Scholar 

  85. Blair, N.E. and Bonner, W.A. (1980)J. Mol. Evol,15, 21.

    Article  Google Scholar 

  86. Tran, C.D. and Fendler, J.H. (1979)J. Am. Chem. Soc,101, 1285.

    Article  Google Scholar 

  87. Tran, C.D. and Fendler, J.H. (1980)J. Am. Chem. Soc,102, 2923.

    Article  Google Scholar 

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Barrett, G.C. (1985). Resolution of Amino Acids. In: Barrett, G.C. (eds) Chemistry and Biochemistry of the Amino Acids. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4832-7_10

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  • DOI: https://doi.org/10.1007/978-94-009-4832-7_10

  • Publisher Name: Springer, Dordrecht

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