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- W2016068449 abstract "The N-alkylated indanylidenepyrroline (NAIP) Schiff base 3 is an unnatural α-amino acid precursor potentially useful for the preparation of semisynthetic peptides and proteins incorporating charged side chains whose structure can be modulated via Z/E photoisomerization. Here we report that the heteroallylic protons of 3 led to partial loss of ethanol accompanied by formation of the novel heterocyclic system 4 during attempted deprotection. We also show that the same protons catalyze the thermal isomerization of 3, making the light-driven conformational control concept ineffective for times longer than a few hours. These problems are not present in the previously unreported compound 5 where the acidic methyl group is replaced by an H atom. Therefore, 5, rather than 3, constitutes a promising prototype for the design of building blocks capable to modulate the electrostatic potential of a protein in specific locations via light irradiation." @default.
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- W2016068449 date "2012-02-02" @default.
- W2016068449 modified "2023-09-25" @default.
- W2016068449 title "Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain" @default.
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- W2016068449 doi "https://doi.org/10.1021/jo2022263" @default.
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