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S‐Acyl cysteine peptides containing α‐, β‐ or γ‐amino acid residues undergo long‐range S‐ to N‐acyl transfer to give analogs of native tripeptides and tetrapeptides containing additional carbon atoms in the chain. The ease of intramolecular S → N‐acyl transfer relative to intermolecular transacylation is favored increasingly for 9 < 12 < 13 ~ 10‐membered cyclic transition states; the observed...
N‐Protected cysteines 4a–c each with a free sulfhydryl group were prepared in 70–75% yields by treatment of l‐cysteine with 1‐(benzyloxycarbonyl) benzotriazole (Cbz‐Bt) 1a, N‐(tert‐butyloxy‐carbonyl)benzotriazole (Boc‐Bt) 1b, and 1‐(9‐fluorenylmethoxy‐carbonyl)benzotriazole (Fmoc‐Bt) 1c, respectively. N‐Protected, free sulfhydryl cysteines 4a–c were then converted into the corresponding N‐protected,...
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