Summary
N, N′-Ethylene-bridged bis-(S)-methionine[(2S, 7S)-2, 7-bis(2-methyl-thioethyl)-3,6-diazaoctanedioic acid] derived from (S)-methionine and 1,2-dibromoethane was cyclized and esterified simultaneously in boiling ethanol in the presence of an appropriate amount of strong acid such asp-toluenesulfonic acid, affording a cyclic compound,N, N′-ethylene-bridged (S)-methionyl-(S)-methionine ethyl ester {ethyl(2S, 3′S)-4-(methylthio)-2-[2′-oxo-3′-(2-methylthioethyl)-1′-piperazinyl] butanoate}, exclusively in 80–90% yields. It was also found that, by applying this method, 70–80% yields of the otherN, N′-ethylenebridged dipeptides containing (S)-tryptophan, -tyrosine and -N(ɛ)-benzyloxycarbonyllysine were obtained.
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Yamashita, T., Takenaka, H. & Kojima, Y. Preparations ofN, N′-ethylene-bridged dipeptides(eXX) constructed from (S)-methionine, -tryptophan, -tyrosine and-N(ɛ)-benzyloxycarbonyllysine through acid-catalyzed cyclization. Amino Acids 4, 187–192 (1993). https://doi.org/10.1007/BF00805814
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DOI: https://doi.org/10.1007/BF00805814