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Constrained Glu‐Gly and Gln‐Gly dipeptide surrogates from γ‐substituted α‐amino‐δ‐lactam synthesis
Author(s) -
Mulamreddy Ramakotaiah,
Lubell William D.
Publication year - 2020
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24149
Subject(s) - dipeptide , lactam , chemistry , amino acid , peptide , stereochemistry , alkylation , olefin fiber , beta lactam , combinatorial chemistry , catalysis , organic chemistry , biochemistry , antibiotics
Conformationally rigid α‐amino‐δ‐lactam surrogates of Glu‐Gly and Gln‐Gly dipeptides have been synthesized from α‐amino‐γ‐vinyl‐δ‐lactam precursors. A reductive cyclization protocol from the respective (4 R )‐ and (4 S )‐2‐ N ‐(Boc)amino‐4‐(azidomethyl)hexenoates gave δ‐lactams, which were converted to the corresponding dipeptide surrogates by N ‐alkylation with methyl bromoacetate. The utility of these α‐amino‐γ‐vinyl‐δ‐lactam building blocks was demonstrated by olefin oxidation and peptide coupling to prepare constrained Glu and Gln residues.