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Retrosulfonamido peptide analogues. Synthesis and crystal conformation of Boc-Pro-Leu-Ψ(NH-SO2)-Gly-NH2

1991; Elsevier BV; Volume: 32; Issue: 46 Linguagem: Inglês

10.1016/s0040-4039(00)93601-3

1873-3581

Giampiero Pagani Zecchini, Mario Paglialunga Paradisi, Ines Torrini, Gino Lucente, E. Gavuzzo, Fernando Mazza, G. Pochetti,

Polyamine Metabolism and Applications

Boc-Pro-Leu-Ψ(NH-SO2)-Gly-NH2 (3) has been synthesized as the first example of a pseudopeptide incorporating the NH-SO2 junction. The crystal structure of 3 indicates that the Ψ(NH-SO2) induces a cisoidal (gauche−) conformation which induces a backbone folding and prevents the H-bonded β-turn found in the parent peptide.