Publication: Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides
Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides
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Breitenmoser, R. A., Linden, A., & Heimgartner, H. (2002). Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides. Helvetica Chimica Acta, 85, 990–1018. https://doi.org/10.1002/1522-2675(200204)85:4<990::AID-HLCA990>3.0.CO;2-6
Abstract
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Abstract
When tripeptides of type Axxt-Aib-Axx-OH were coupled with amino acid methyl esters by means of commonly used coupling reagents, the formation of 1,3-thiazol-5(4H)-imines and 1,3-oxazol-5(4H)-imines was observed. With the aim of understanding which structure elements are required for this reaction, several model peptides have been prepared according to our recently described methodology, a modification of the 'azirine/oxazolone method', followed by selective isomerization of the peptide thioamides. In addition, attempts to prepare pep
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- Breitenmoser, Roland A
- Heimgartner, Heinz
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Breitenmoser, R. A., Linden, A., & Heimgartner, H. (2002). Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides. Helvetica Chimica Acta, 85, 990–1018. https://doi.org/10.1002/1522-2675(200204)85:4<990::AID-HLCA990>3.0.CO;2-6
