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The resulting products are ser, ind, and in the case of free trp also gly, ala, asp, and aminobenzoic acid. The influence of the neighboring amino acids in peptides containing trp on the degradation of trp was investigated with the dipeptides ala-trp and phe-trp. The reactions were carried out under similar reaction conditions in order to ascertain whether similar reaction products can be detected. The reactions were, however, only conducted in neutral and weak alkaline media because differences in reaction products seemed to be evident between these pH conditions.
100 ~l trifluoroacetic acid and 10 ~l butylmercaptan were added and the vials were closed. The solutions were heated at l60-l65·C for 25 min, and concentrated to dryness with Nz at 80·C. The residues were derivatized for gc determination. Recovery of trp was 100% (ala-trp) and 84% (phetrp). Recovery of ala was 100% and of phe 94%. Apparatus: Gc determinations of trp degradation products were carried out with a Hewlett Packard gc 5700 A equipped with a capillar-gc addition (Fa. 25 ~m film thickness.
Lomln. (L). X-Z_H. Y-Br b(lQ. Z_Br c(C). X-H. Z_Br dIE). ,2hr BOCHNksCH3 H H HC H BOCHN~SCH3 D-Cysteina' I D-Cystine mp. S'C TFA(laq) CH,CI, 51. N-~H et£t[ '" I . ,Smln. ,20mln 3) NaOMa ) BocHN S N , N H ... H; R2 -Ac 3 steps; 75-/. ~H"" • ~ ".. 1 I N... H Br~N"'O - 2)Ambarlll. IRA-400 76% ~~:;:L) H,N (-)Eudistomln L (a)o -58 3' S Sla Scheme 12 Scientific Research (62470134 and 63105005) from the Ministry of Education, Science, and Culture, Japan and Uehara Memorial Foundation. , 1979, Aromatization of arene l,2-oxides.