Synthesis of Pseudopeptides with Sulfoximines as Chiral Backbone Modifying Elements

✍ Scribed by Carsten Bolm; Guido Moll; Jan D. Kahmann

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 208 KB
• Volume: 7
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20010302)7:5<1118::aid-chem1118>3.0.co;2-3

✦ Synopsis

The synthesis of pseudopeptides with a chiral a-sulfonimidoylcarboxy moiety in the backbone is described. Starting from readily available (S S )-S-methyl Sphenyl sulfoximine and various cyclic and acyclic a-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.