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- W1982227676 abstract "The asymmetric synthesis of (S)-Boc-p-(propanoyl)phenylalanine (10) was performed by alkylation of sultam N-(diphenylmethylene)glycinate (4). Different pathways for the introduction of a phenylseleno moiety α to the ketone function were investigated. (S)-Boc-p-[2′-(phenylselenenyl)propanoyl]phenylalanine (11) was easily obtained from (S)-Boc-p-(propanoyl)phenylalanine (10). However, the phenylseleno moiety α to the carbonyl group was found to be unstable to the conditions required for solid-phase peptide synthesis. Therefore, (2S)-Boc-p-[2′-(phenylselenenyl)propanoyl]phenylalanine (11) was transformed into Boc-p-[3′-(phenylselenenyl)propanoyl]phenylalanine (13), which was successfully incorporated into the sequence of a model peptide. The corresponding enone function generated under mild acidic conditions was found to be stable in aqueous solution at pH = 7, but suitably reactive upon irradiation. Thus, these phenylalanine analogs bearing an unsaturated ketone represent new photoreactive probes. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)" @default.
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- W1982227676 date "2002-05-01" @default.
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- W1982227676 title "Synthesis of New Photoactivatable Phenylalanine Analogues and Their Incorporation into a Model Peptide − Phenylseleno Derivatives as Precursors of α,β-Unsaturated Ketones in Peptide Synthesis" @default.
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- W1982227676 doi "https://doi.org/10.1002/1099-0690(200205)2002:10<1677::aid-ejoc1677>3.0.co;2-8" @default.
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