Publication: Selektive Amidspaltung bei Peptiden mit alpha,alpha-disubstituierten alpha-Aminosäuren
Selektive Amidspaltung bei Peptiden mit alpha,alpha-disubstituierten alpha-Aminosäuren
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Citations
Wipf, P., & Heimgartner, H. (1987). Selektive Amidspaltung bei Peptiden mit alpha,alpha-disubstituierten alpha-Aminosäuren. Helvetica Chimica Acta, 70, 354–368. https://doi.org/10.1002/hlca.19870700213
Abstract
Abstract
Abstract
A new synthesis of dipeptides with terminal alpha,alpha-disubstituted alpha-amino acids, using 2,2-disubstituted 3-amino-2H-azirines 1 as amino-acid equivalents, is demonstrated. The reaction of 1 with N-protected amino acids leads to the corresponding dipeptide amides in excellent yield. It is shown that the previously described selective hydrolysis (HCl, toluene, 80°, or HCI, MeCN/H2O, 80°) of the terminal amide group results in an extensive epimerization of the second last amino acid. An acid-catalyzed enolization in the intermedia
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Creators (Authors)
- Wipf, Peter
- Heimgartner, Heinz
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Citations
Wipf, P., & Heimgartner, H. (1987). Selektive Amidspaltung bei Peptiden mit alpha,alpha-disubstituierten alpha-Aminosäuren. Helvetica Chimica Acta, 70, 354–368. https://doi.org/10.1002/hlca.19870700213
