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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 4 (1998), S. 46-57 
    ISSN: 1075-2617
    Keywords: α-hydroxymethylserine peptides ; isopropylidene protecting group ; crystal structure ; peptide conformation ; peptide synthesis ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A synthetic methodology has been developed for peptide bond formation with α-hydroxmethylserine as the carboxyl or amino component and also for the preparation of homo-sequences. The key intermediate, O,O-protected α-hydroxymethylserine in the form of an isopropylidene derivative, is easily accessible and represents the first example of a heterocyclic Cα,α-disubstituted amino acid containing an 1,3-dioxane ring. The use of this intermediate facilitates protection of the sterically hindered amino and carboxyl groups and is advantageous for the coupling and deprotection steps. X-ray structure determination of Z-HmS(Ipr)-Ala-OMe revealed that the two crystallographically independent molecules present in the asymmetric unit adopt an S-shaped conformation. In the one molecule the achiral HmS(Ipr) residue has the torsion angle values (φ==61.4°,ψ=40.8°) in the left-handed helical region of the Ramachandran map, while in the second molecule the negative torsion angles (φ=-60.1°, ψ=-44.4°) are associated with the right-handed helix. © 1998 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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