J. Lohier, K. Wright, C. Peggion
Jun 26, 2006
Citations
0
Influential Citations
18
Citations
Journal
Tetrahedron
Abstract
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.