ISSN:
1434-193X
Keywords:
Asymmetric synthesis
;
Peptides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A sulfahydantoin (3-oxo-1,2,5-thiadiazolidine 1,1-dioxides) motif is used as a new type of peptidic constraint to lock two consecutive amide nitrogens by a sulfonyl bridge. The 5-membered heterocyclic motif was prepared starting from proteogenic and synthetic amino acids and chlorosulfonyl isocyanate. Constrained dipeptides were obtained under alkaline conditions (methoxide or tert-butoxide) by cyclization of symmetric and dissymmetric sulfamides. The absolute configuration of the chiral centers for the derivative L-Phe-D-Ala, a congener of the series, was established by X-ray diffraction crystallographic analysis. In addition, the chemo-, regio-, and stereoselectivities of the reactions were studied. In the acylated derivatives, the sulfahydantoin constraint induces a unique backbone conformation with coplanarity of two consecutive peptide bonds.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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