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Synthesis of Pseudopeptides with Sulfoximines as Chiral Backbone Modifying Elements
Author(s) -
Bolm Carsten,
Moll Guido,
Kahmann Jan D.
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010302)7:5<1118::aid-chem1118>3.0.co;2-3
Subject(s) - moiety , intramolecular force , hydrogen bond , chemistry , combinatorial chemistry , amino acid , peptide , stereochemistry , molecule , organic chemistry , biochemistry
The synthesis of pseudopeptides with a chiral α‐sulfonimidoylcarboxy moiety in the backbone is described. Starting from readily available ( S S )‐ S ‐methyl S ‐phenyl sulfoximine and various cyclic and acyclic α‐amino acids the desired products are obtained in good yields with peptide coupling methodology. Specific secondary structures caused by intramolecular hydrogen bonds may be adopted. Results of NMR studies to reveal conformational preferences will be discussed.