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Preparation of Constrained Unnatural Aromatic Amino Acids via Unsaturated Diketopiperazine Intermediate
Author(s) -
Mollica Adriano,
Costante Roberto,
Mirzaie Sako,
Carradori Simone,
Macedonio Giorgia,
Stefanucci Azzurra,
Novellino Ettore
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2489
Subject(s) - chemistry , cyclic peptide , amino acid , peptide , aromatic amino acids , stereochemistry , tyrosine , alanine , side chain , diketopiperazines , combinatorial chemistry , organic chemistry , biochemistry , polymer
Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′‐dimethyl‐tyrosine and 2′,6′‐dimehylphenyl‐alanine derivatives as handling building blocks for peptide synthesis via unsaturated diketopiperazine (DKP) intermediate .