A new and efficient synthesis of unnatural amino acids and peptides by selective 3, 3-dimethyldioxirane side-chain oxidation

…, I Torrini, MP Paradisi, G Mastropietro

文献索引：Saladino, Raffaele; Mezzetti, Maurizio; Mincione, Enrico; Torrini, Ines; Paradisi, Mario Paglialunga; Mastropietro, Gaia Journal of Organic Chemistry, 1999 , vol. 64, # 23 p. 8468 - 8474

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被引用次数: 28

摘要

N-Boc derivatives of Leu, Met, Thr, Trp, and Pro, the properties of which resemble those of the respective α-amino acid residues present in proteins, rapidly oxidize in the presence of 3, 3-dimethyldioxirane to give different products depending on the structure of the oxidizable group in the side chain. A high regioselectivity for the oxygen atom insertion into the γ-CH bond of Leu residues with respect to the weaker α-CH bond was observed. A position ...