Synthesis of the endothiopeptide BOC-Trp-Ile-Ala-Aib-Ile-ValΨ[CSNH]Aib-Leu-Aib-Pro-OMe by a variation of the ‘azirine/oxazolone method’

✍ Scribed by Jürg Lehmann; Anthony Linden; Heinz Heimgartner

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 900 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00506-7

✦ Synopsis

The synthesis of the decaendothiopepfide BOC-Trp-Ile-Ala-Aib-lle-Val~F[CSNH]Aib-Leu -Aib-Pro-OMe is described. The introduction of the thioamide group next to the bulky Aib occurred via a variation of the 'azirine/oxazolone method' without epimerisation. The structure of the decaendothiopeptide was etablished by single-crystal X-ray crystallography, thereby two types of helices could be observed.