Publication: Kupplung von Peptiden mit C-terminalen alpha,alpha-disubstituierten alpha-Aminosäuren via Oxazol-5(4H)-one
Kupplung von Peptiden mit C-terminalen alpha,alpha-disubstituierten alpha-Aminosäuren via Oxazol-5(4H)-one
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Wipf, P., & Heimgartner, H. (1986). Kupplung von Peptiden mit C-terminalen alpha,alpha-disubstituierten alpha-Aminosäuren via Oxazol-5(4H)-one. Helvetica Chimica Acta, 69(5), 1153–1162. https://doi.org/10.1002/hlca.19860690524
Abstract
Abstract
Abstract
The formation of peptide bonds between dipeptides 4 containing a C-terminal alpha,alpha-disubstituted alpha-amino acid and ethyl p-aminobenzoate (5) using DCC as coupling reagent proceeds via 4,4-disubstituted oxazol-5(4H)-ones 7 as intermediates (Scheme 3). The reaction yielding tripeptides 6 (Table 2) is catalyzed efficiently by camphor-10-sulfonic acid (Table 1).The main problem of this coupling reaction is the epimerization of the nonterminal amino acid in 4 via a mechanism shown in Scheme 1. CSA catalysis at 0° suppresses complet
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- Wipf, Peter
- Heimgartner, Heinz
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Citations
Wipf, P., & Heimgartner, H. (1986). Kupplung von Peptiden mit C-terminalen alpha,alpha-disubstituierten alpha-Aminosäuren via Oxazol-5(4H)-one. Helvetica Chimica Acta, 69(5), 1153–1162. https://doi.org/10.1002/hlca.19860690524
