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- W2017484823 abstract "Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-d-serine-β-lactone (6) with Boc-l-His-OMe (5) gave a 2:1 mixture of τ- and π-regioisomers. The sulfamidate 10, derived from N-benzyl-d-serine methyl ester (11), was reacted with Boc-l-His-OMe (5) to give the τ-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared τ-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, τ-l-histidinyl-d-alanine (τ-4), as a salt-free standard for amino acid analysis." @default.
- W2017484823 created "2016-06-24" @default.
- W2017484823 creator A5016593302 @default.
- W2017484823 creator A5042948427 @default.
- W2017484823 date "2011-06-14" @default.
- W2017484823 modified "2023-09-23" @default.
- W2017484823 title "Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles" @default.
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- W2017484823 doi "https://doi.org/10.1021/jo200744d" @default.
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