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'

DOI: 10.1016/S0040-4020(98)00506-7

Source and publish data:

Tetrahedron p. 8721 - 8736 (1998)

Update date:2022-08-04

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Authors:

Lehmann, Juerg

Linden, Anthony

Heimgartner, Heinz

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Article abstract of DOI:10.1016/S0040-4020(98)00506-7

The synthesis of the decaendothiopeptide BOC-Trp-Ile-Ala-Aib-Ile- ValΨ[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 established by single-crystal X-ray crystallography, thereby two types of helices could be observed.

Full text of DOI:10.1016/S0040-4020(98)00506-7

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