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(S)-beta3-homolysine- and (S)-beta3-homoserine-containing beta-peptides: CD spectra in aqueous solution

For further structural studies and for physiological investigations of beta-peptides, it is necessary to have H2O-soluble derivatives. Thus, we have prepared beta-hexa-, beta-hepta-, and beta-nonapeptides (1-6) with two, three, and seven side chains of lysine and serine. To detect possible pi-pi interactions, we also included the beta-amino acid beta2-HHop, resulting from homologation of so-called homophenylalanine (Hop) (5 and 6). The Fmoc-beta2- and beta3-amino-acid derivatives (11-14 and 19), and the corresponding beta- peptides were prepared by methods previously described (solid-phase peptide coupling; HPLC-pure samples, Fig. 1). Circular-dichroism spectra (Fig. 2) indicate the presence of less pronounced secondary structures (especially of the lysine analogues with multiple positive charge) in H2O as compared to MeOH. The beta3-heptapeptide (3) with two serine side chains is well soluble in H2O and exhibits the CD pattern typical of the 31-helical structure.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1706NO – PubChem