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Sulfahydantoins as Tripeptide Constraints: Synthesis and Structure of Chiral Substituted 3-Oxo-1,2,5-thiadiazolidine 1,1-Dioxides

✍ Scribed by Sihem Boudjabi; Georges Dewynter; Normand Voyer; Loïc Toupet; Jean-Louis Montero

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
322 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

A sulfahydantoin (3-oxo-1,2,5-thiadiazolidine 1,1-dioxides) absolute configuration of the chiral centers for the derivative L-Phe-D-Ala, a congener of the series, was established by X-motif is used as a new type of peptidic constraint to lock two consecutive amide nitrogens by a sulfonyl bridge. The 5-ray diffraction crystallographic analysis. In addition, the chemo-, regio-, and stereoselectivities of the reactions were membered heterocyclic motif was prepared starting from proteogenic and synthetic amino acids and chlorosulfonyl studied. In the acylated derivatives, the sulfahydantoin constraint induces a unique backbone conformation with isocyanate. Constrained dipeptides were obtained under alkaline conditions (methoxide or tert-butoxide) by coplanarity of two consecutive peptide bonds. cyclization of symmetric and dissymmetric sulfamides. The because they present side chains in a highly accessible ar-

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