The presentation of Z-NH2(Benzyl carbamate)

This addition describes the amalgam and ring-opening (co)polymerization of several l-lysine Z-NH2(Benzyl carbamate) that accommodate labile careful groups at the ϵ-NH2 position. Four of the afterward l-lysine NCAs were investigated: Nϵ-trifluoroacetyl-l-lysine N-carboxyanhydride, Nϵ-(tert-butoxycarbonyl)-l-lysine N-carboxyanhydride, Nϵ-(9-fluorenylmethoxycarbonyl)-l-lysine N-carboxyanhydride, and Nϵ-(6-nitroveratryloxycarbonyl)-l-lysine N-carboxyanhydride. In adverse to the acrid altitude that are appropriate for acidolysis of Z-NH2(Benzyl carbamate) moieties, which are usually acclimated to assure the ϵ-NH2 position of l-lysine during NCA polymerization, the careful groups of the l-lysine NCAs presented actuality can be removed beneath agilely acerb or basal altitude or by photolysis. As a consequence, these monomers may acquiesce admission to atypical peptide amalgam abstracts that cannot be able from ϵ-benzyloxycarbonyl-l-lysine N-carboxyanhydride (Z-Lys NCA) because of ancillary reactions that accompany the abatement of the Z groups. By copolymerization of these l-lysine NCAs with labile careful groups, either with anniversary added or with γ-benzyl-l-glutamate N-carboxyanhydride or Z-Lys NCA, orthogonally side-chain-protected copolypeptides with number-average degrees of polymerization ≤20 were obtained. Such copolypeptides, which accommodate altered side-chain careful groups that can be removed independently, are absorbing for the amalgam of circuitous polypeptide architectures or can be acclimated as scaffolds for the alertness of constructed antigens or protein mimetics.Z-NH2(Benzyl carbamate) compounds acquired from felbamate were actinic and 11 ambition compounds (1, 4, and 6–14) were initially evaluated in mice MES and PTZ models in our laboratory. Z-NH2(Benzyl carbamate) with capricious substituents on the oxygen (1–4) gave anticonvulsant action with a advanced ambit of ED50 in MES analysis from <20 mg/kg (2) to >300 mg/kg (4) and compounds with altered groups on the nitrogen (5–14) aswell were absolutely alive in the ambit of 15 mg/kg (14) to 170.5 mg/kg (6).
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