• 87. Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes

    We report the first direct catalytic method for formyl-selective deuterium labeling of aromatic aldehydes under mild conditions, using an iridium-based catalyst designed to favor formyl over aromatic C−H activation. A good range of aromatic aldehydes is selectively labeled, and a one-pot labeling/olefination method is also described. Computational studies support kinetic product control over competing aromatic […]

    Kerr, W. J.; Reid, M.; Tuttle, T.

    Angew. Chem. Int. Ed. 2017 56 7808.

  • 86. Polymeric peptide pigments with sequence-encoded properties

    Melanins are a family of heterogeneous polymeric pigments that provide ultraviolet (UV) light protection, structural support, coloration, and free radical scavenging. Formed by oxidative oligomerization of catecholic small molecules, the physical properties of melanins are influenced by covalent and noncovalent disorder. We report the use of tyrosine-containing tripeptides as tunable precursors for polymeric pigments. In […]

    Lampel, A.; McPhee, S. A.; Park, H-A.; Scott, G. G.; Humagain, S.; Hekstra, D. R.; Barney Yoo, B.; Frederix, P. W. J. M.; Li, T-D.; Abzalimov, R. R.; Greenbaum, S. G.; Tuttle, T.; Hu, C.; Betting, C. J.; Ulijn, R. V.

    Science 2017 356 1064.

  • 85. Biocatalytic Self-Assembly of Tripeptide Gels and Emulsions

    We report on the biocatalytic activation of a self-assembling (unprotected) tripeptide to stabilize oil-in-water emulsions on-demand. This is achieved by the conversion of a phosphorylated precursor into a hydrogelator using alkaline phosphatase (AP) as the trigger. The rate of conversion, controlled by the amount of enzyme used, is shown to play a key role in […]

    Moreira, I. P.; Piskorz, T. K.; van Esch, J. H.; Tell Tuttle, T.; Ulijn, R. V.

    Langmuir 2017 33 4986.

  • 84. A study of diketopiperazines as electron-donor initiators in transition metal-free haloarene–arene coupling.

    The electron-donating ability of enolates of N,N′-disubstituted diketopiperazines is strongly influenced by the nature of the substituents.

    Cumine, F.; Zhou, S.; Tuttle, T.; Murphy, J. A.

    Org. Biomol. Chem. 2017 15 3324.