Preparations ofN, N'-ethylene-bridged dipeptides(eXX) constructed from (S)-methionine, -tryptophan, -tyrosine and-N(ɛ)-benzyloxycarbonyllysine through acid-catalyzed cyclization.

Abstract:

: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.

journal_name

Amino Acids

journal_title

Amino acids

authors

Yamashita T,Takenaka H,Kojima Y

doi

10.1007/BF00805814

subject

Has Abstract

pub_date

1993-02-01 00:00:00

pages

187-92

issue

1-2

eissn

0939-4451

issn

1438-2199

journal_volume

4

pub_type

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