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  • Title: Conformations of peptides containing a chiral cyclic α, α-disubstituted α-amino acid within the sequence of Aib residues.
    Author: Demizu Y, Tanaka M, Doi M, Kurihara M, Okuda H, Suemune H.
    Journal: J Pept Sci; 2010 Nov; 16(11):621-6. PubMed ID: 20853311.
    Abstract:
    A single chiral cyclic α,α-disubstituted amino acid, (3S,4S)-1-amino-(3,4-dimethoxy)cyclopentanecarboxylic acid [(S,S)-Ac(5)c(dOM)], was placed at the N-terminal or C-terminal positions of achiral α-aminoisobutyric acid (Aib) peptide segments. The IR and (1)H NMR spectra indicated that the dominant conformations of two peptides Cbz-[(S,S)-Ac(5)c(dOM)]-(Aib)(4)-OEt (1) and Cbz-(Aib)(4)-[(S,S)-Ac(5)c(dOM)]-OMe (2) in solution were helical structures. X-ray crystallographic analysis of 1 and 2 revealed that a left-handed (M) 3(10)-helical structure was present in 1 and that a right-handed (P) 3(10)-helical structure was present in 2 in their crystalline states.
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