Publication: Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons
Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons
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Stamm, S., & Heimgartner, H. (2006). Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons. Helvetica Chimica Acta, 89(9), 1841–1855. https://doi.org/10.1002/hlca.200690178
Abstract
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Abstract
The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons for the Aib-Pro unit in peptide synthesis. After incorporation into the peptide by means of the 'azirine/oxazolone method', the C-termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd0-promoted procedure, respectively.
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Stamm, S., & Heimgartner, H. (2006). Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons. Helvetica Chimica Acta, 89(9), 1841–1855. https://doi.org/10.1002/hlca.200690178