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Synthesis of α-tritiated L-histidine, L-arginine and L-lysine

✍ Scribed by Albert A. Plentl; William T. Kelly

Publisher
Elsevier Science
Year
1966
Tongue
English
Weight
934 KB
Volume
17
Category
Article
ISSN
0003-2697

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✦ Synopsis

For physiological investigations on the transfer of met,abolites in the pregnant organism it was necessary to prepare a number of natural amino acids with a specific tritium label. The present report relates to the introduction of tritium into the a-position of the basic amino acids, histidine, arginine and lysine. Racemization procedures of optically active amino acids in a tritiated medium were selected to accomplish this. Of the many known variations the azlactone rearrangement described by Bergmann and Zervas (1) and du Vigneaud and Meyer (2) seemed particularly well suited for this purpose because of the mild conditions and the possibility of a nearly quantitative recovery of the isotope. The mechanism of this reaction is outlined in Scheme I. That the reaction proceeds essentially as predicted has been shown by Clark and Rittenberg (3), who applied a modification of this reaction for the introduction of deuterium into the a-position of lysine.

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