58238-09-8Relevant articles and documents
Simple Peptides. VII. The Chemical Conversions of C-Terminal α-Amino Acids in Peptides into Unsubstituted or 2-Substituted Taurine via S-Acetylthio- or Halogeno-Intermediates
Higashiura, Kunihiko,Ienaga, Kazuharu
, p. 1901 - 1921 (2007/10/02)
The syntheses of ten dipeptides 5a-c, e, f, h-j, l and m, containing taurine or its 2-substituted derivatives, are described: C-terminal a-amino acids in the dipeptides were chemically converted to the taurines by two main routes.One involves the successive conversion of N-tert-butoxycarbonyl(Boc)-protected dipeptide esters 1 into the 2-(Boc-aminoacyl)aminoethanols 2 and thence into their acetylthio derivatives 4 via β-bromoethylamides 3, followed by the performic acid oxidation of the acetylthio into a sulpho group to give the deprotected taurine dipeptides 5.In the other, 2 was converted into 5 using the substitution reaction of a sulpho group for a halogen or mesyl group via the corresponding β-halogenoethyl or β-(methanesulphonyl)-oxyethyl amides, 3,9 or 7.The preparation of intrinsic γ-L-Glu-Tau (glutaurine) 12a and its D-isomer 12b from the acetylthio derivatives 11a and 11b by performic acid oxidation is also described as examples of the use of S-acetylcysteamine for a taurine precursor.
