Synthesis of protected derivatives and short peptides of antAib, a novel C-tetrasubstituted α-amino acid of the Ac5c type possessing a fused anthracene fluorophore |
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Authors: | Jean-Franç ois Lohier,Cristina Peggion,Claudio Toniolo,Michel Wakselman |
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Affiliation: | a Institut Lavoisier, UMR CNRS 8180, University of Versailles, F-78035 Versailles, France b Department of Chemistry, University of Padova, I-35131 Padova, Italy |
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Abstract: | The Nα-Boc and Nα-Fmoc protected derivatives of 2-amino-2,3-dihydro-1H-cyclopenta[b]anthracene-2-carboxylic acid (antAib), a novel fluorescent, achiral, α-amino acid, rigid analogue of the known 9-antAla and 2-antAla residues, and belonging to the class of Ciα→Ciα cyclized, Cα,α-disubstituted glycines (strong β-turn and helix inducers in peptides), were synthesized in seven steps from 1,2,4-trimethylbenzene. The UV absorption and fluorescence properties of Boc-antAib-OEt and Boc-antAib-OH are also described. Solution syntheses of the short peptides Boc-antAib-l-Ala-OMe, Fmoc-l-Ala-antAib-l-Ala-OMe, as well as Boc-Aib-antAib-l-Ala-OMe and the side product 2,5-dioxopiperazine cyclo-[antAib-l-Ala], are presented as examples of the coupling ability at both C- and N-termini of the antAib residue. |
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Keywords: | Anthracene Aromatic amino acid Cα,α-Disubstituted glycine Fluorescent amino acid |
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