ISSN:
1438-2199
Keywords:
Amino acids
;
Acid-catalyzed cyclization
;
N, N′-Ethylene-bridged dipeptides
;
(S)-Methionine
;
(S)-Tryptophan
;
(S)-Tyrosine
;
(S)-N(ɛ)-Benzyloxy-carbonyllysine
Source:
Springer Online Journal Archives 1860-2000
Topics:
Medicine
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00805814
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