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Abstract

A century ago it was first observed that amino acids underwent racemization when heated in strongly acidic and basic solutions. It soon became well established that the optically active amino acids isolated from biological materials could be converted into a racemic mixture by a variety of rather vigorous treatments. In the early part of the 20th century the first observations of amino acid racemization in peptides and proteins in alkaline solutions at elevated temperatures were reported. The interpretation of these measurements was complicated by peptide-bond hydrolysis and the realization that racemization rates probably depended on whether amino acids were at terminal or internal positions in the peptide. The earlier work on amino acid racemization in various systems was extensively reviewed in 1948 by Neuberger [1].

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References

  1. Neuberger, A. (1948)Adv. Protein Chem,4, 298.

    Google Scholar 

  2. Bada, J.L. (1971)ACS Adv. Chem. Ser. No 106, 309.

    Google Scholar 

  3. Bada, J.L. (1972)J. Am. Chem. Soc,94, 1371.

    Article  Google Scholar 

  4. Bada, J.L. and Schroeder, R.A. (1975)Naturwissenschaften,62, 71.

    Article  Google Scholar 

  5. Schroeder, R.A. and Bada, J.L. (1976)Earth Sci. Rev,12, 347.

    Article  Google Scholar 

  6. Williams, H.M. and Smith, G.G. (1977)Origins of Life,8, 91.

    Article  Google Scholar 

  7. Vicar, J. (1977)Chemicke Listy,71, 160.

    Google Scholar 

  8. Bada, J.L. (1982)Interdispl. Sci. Revs,7, 30.

    Google Scholar 

  9. Finley, T.H. and Adams, E. (1970)J. Biol. Chem,245, 5248.

    Google Scholar 

  10. Smith, G.G., Williams, K.M. and Wonnacott D.M. (1978)J. Org. Chem,43, 1.

    Article  Google Scholar 

  11. Dungworth, G., Vincken, N.J. and Schwarz, A.W. (1973) inAdvances in Organic Geochemistry(eds B. Tissat and F. Bienner), Technip, Paris, p. 689.

    Google Scholar 

  12. Masters, P.M. and Friedman, M. (1980)ACS Symposium Series No.123, 165.

    Article  Google Scholar 

  13. Smith, G.G. and de Sol, B.S. (1980)Science,207, 765.

    Article  Google Scholar 

  14. Shou, M.-Y. (1979)Ph.D. Thesis, Scripps Institution of Oceanography, University of California, San Diego.

    Google Scholar 

  15. Bada, J.L. and Shou, M.-Y. (1980) inBiogeochemistry of Amino Acids(eds P.E. Hare, T.C. Hoering and K. King), Wiley, New York, p. 235.

    Google Scholar 

  16. Cram, D.J. (1964) inFundamentals of Carbanion Chemistry, Academic Press, New York.

    Google Scholar 

  17. Barlin, C.B. and Perrin, D.D. (1966)Quart. Rev. Chem. Soc., Lond,20, 75.

    Article  Google Scholar 

  18. Taft, R.W. (1956) inSteric Effects in Organic Chemistry(ed. M.S. Neuman), Wiley, New York, p. 556.

    Google Scholar 

  19. Kemp, D.S. (1979) inThe Peptides; Analysis, Synthesis and Biology (eds E. Gross and J. Meienhofer) (Vol. 1) Academic Press, New York, p. 315.

    Google Scholar 

  20. Buckingham, D.A., Marzilli, L.G. and Sargeson, A.M. (1967)J. Am. Chem. Soc,89, 5133.

    Article  Google Scholar 

  21. Pasini, A. and Cassella, L. (1974)J. Inorg. Nucl. Chem,36, 2133.

    Article  Google Scholar 

  22. Gillard, R.D., O’Brien, P., Norman, P.R. and Phipps, D.A. (1977)J. Chem. Soc. Dalton,1977, 1988.

    Article  Google Scholar 

  23. Gillard, R.D. and O’Brien, P. (1978)J. Chem. Soc. Dalton,1978, 1444.

    Article  Google Scholar 

  24. Snell, E.E., Braunstein, A.E., Severin, E.S. and Torchinsky, Y.M. (eds)Pyridoxal Catalysis Enzymes and Model Systems, Interscience, New York.

    Google Scholar 

  25. Gund, P. and Veber, D.F. (1979)J. Am. Chem. Soc,101, 1885.

    Article  Google Scholar 

  26. Bohak, Z. and Katchalski, E. (1963)Biochemistry,2, 228.

    Article  Google Scholar 

  27. Kriausakul, N. and Mitterer, R. (1978)Science,201, 1011.

    Article  Google Scholar 

  28. Steinberg, S. and Bada, J.L. (1981)Science,213, 544.

    Article  Google Scholar 

  29. Steinberg, S. (1982)Ph.D. thesis, Scripps Institution of Oceanography, University of California, San Diego.

    Google Scholar 

  30. Smith, G.G. and Evans, R.C. (1980) inBiogeochemistry of Amino Acids(eds P.E. Hare, T.C. Hoering and K. King), Wiley, New York, p. 257.

    Google Scholar 

  31. Helfman, P. M. and Bada, J.L. (1976)Nature,262, 279.

    Article  Google Scholar 

  32. Masters, P.M., Bada, J.L. and Zigler, J.S. (1977)Nature,268, 71.

    Article  Google Scholar 

  33. Masters, P.M., Bada, J.L. and Zigler, J.S. (1978)Proc. Natl. Acad. Sci. USA,75, 1204.

    Article  Google Scholar 

  34. Garner, W.H. and Spector, A. (1978)Proc. Nad. Acad. Sci. USA,75, 3618.

    Article  Google Scholar 

  35. Friedman, M. and Masters, P. M. (1982)J. Food. Sci,47, 760.

    Article  Google Scholar 

  36. Engel, M.H., Sawyer, T.K., Hadley, M.E. and Hruby, V.J. (1981)Anal. Biochem,116, 303.

    Article  Google Scholar 

  37. Helfman, P. M., Bada, J.L. and Shou, M.-Y. (1977)Gerontology,23, 419.

    Article  Google Scholar 

  38. Koeppe, R.H. and Stroud, R.M. (1976)Biochemistry,15, 3450.

    Article  Google Scholar 

  39. Engel, M.H., and Hare, P.E. (1981)Carnegie Inst. Wash. Yearbook,80, 400.

    Google Scholar 

  40. Whitaker, J.R. (1980)ACS Symposium Series No.123, p. 145.

    Article  Google Scholar 

  41. Ott, H., Frey, A.J. and Hofmann, A. (1963)Tetrahedron,19, 1675.

    Article  Google Scholar 

  42. Vicar, J. and Blaha, K. (1973)Collection Czechoslov. Chem. Commun,38, 3307.

    Google Scholar 

  43. Dungworth, G. (1976)Chem. Geol,17, 135.

    Article  Google Scholar 

  44. Pautet, F. (1980)Pathol. Biol,25, 325.

    Google Scholar 

  45. Belluomini, G. (1981)Archaeometry,23, 125.

    Article  Google Scholar 

  46. Bada, J.L. (1981)Earth Planet. Sci. Iett,55, 292.

    Article  Google Scholar 

  47. Bada, J.L., Brown, S. and Masters, P.M. (1980) inAge Determinations of Toothed Whales and Sirenians(eds W.F. Perrin and A.C. Myrick), International Whaling Commission, Special Issue 3, Cambridge, England, p. 113.

    Google Scholar 

  48. McFadden, P.N. and Clarke, S. (1982)Proc. Natl. Acad. Sci. USA,79, 2460.

    Article  Google Scholar 

  49. Masters, P.M. and Friedman, M. (1979)J. Agr. Food Chem,27, 507.

    Article  Google Scholar 

  50. Hayashi, R. and Kameda, I. (1980)J. Food Sci,45, 1430.

    Article  Google Scholar 

  51. Hayashi, R. and Kameda, I. (1980)Agr. Biol. Chem,44, 891.

    Article  Google Scholar 

  52. Friedman, M., Zahnley, J.C. and Masters, P.M. (1981)J. Food Sci,46, 127.

    Article  Google Scholar 

  53. Engel, M.H. and Hare, P.E. (1981)Carnegie Inst. Wash. Yearbook,80, 394.

    Google Scholar 

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Bada, J.L. (1985). Racemization 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_13

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  • DOI: https://doi.org/10.1007/978-94-009-4832-7_13

  • Publisher Name: Springer, Dordrecht

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