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A synthetic protocol is described which allows the incorporation of the γ-amide (Kan) and the γ-benzyl ester [Kai(Bzl)] and ether [Kol(Bzl)] of kainic acid (Kai) into peptide chains as exemplified with the synthesis of the substance P (SP) analogs [Kan 5 ]-SP 5−11 , [Glp 5 . Kan 6 ]-SP 5−11 . [Kan 6 ]-SP 6 11 .[Glp 5 . Kai(Bzl) 11...
Reactions of N-tritylaspartic acid anhydride, readily available through N,N -dicyclohexylcarbodiimide-mediated dehydration of N-tritylaspartic acid, with Grignard and Wittig reagents, bulky hydrides, and amines or alcohols of the benzhydryl type, lead regioselectively to products from attack at the β-carbonyl function.
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