Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions

Frese M, Schnepel C, Minges H, Voss H, Feiner R, Sewald N (2016)
CHEMCATCHEM 8(10): 1799-1803.

Journal Article | Published | English

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Abstract
The combination of the biocatalytic halogenation of l-tryptophan with subsequent chemocatalytic Suzuki-Miyaura crosscoupling reactions leads to the modular synthesis of an array of C5, C6, or C7 aryl-substituted tryptophan derivatives. In a three-step one-pot reaction, the bromo substituent is initially incorporated regioselectively by immobilized tryptophan 5-, 6-, or 7-halogenases, respectively, with concomitant cofactor regeneration. The halogenation proceeds in aqueous media at room temperature in the presence of NaBr and O-2. After the separation of the biocatalyst by filtration, a Pd catalyst, base, and boronic acid are added to the aryl halide formed in situ to effect direct Suzuki-Miyaura cross-coupling reactions followed by tert-butoxycarbonyl (Boc) protection. After a single purification step, different Boc-protected aryl tryptophan derivatives are obtained that can, for example, be used for peptide or peptidomimetic synthesis.
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Frese M, Schnepel C, Minges H, Voss H, Feiner R, Sewald N. Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions. CHEMCATCHEM. 2016;8(10):1799-1803.
Frese, M., Schnepel, C., Minges, H., Voss, H., Feiner, R., & Sewald, N. (2016). Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions. CHEMCATCHEM, 8(10), 1799-1803.
Frese, M., Schnepel, C., Minges, H., Voss, H., Feiner, R., and Sewald, N. (2016). Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions. CHEMCATCHEM 8, 1799-1803.
Frese, M., et al., 2016. Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions. CHEMCATCHEM, 8(10), p 1799-1803.
M. Frese, et al., “Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions”, CHEMCATCHEM, vol. 8, 2016, pp. 1799-1803.
Frese, M., Schnepel, C., Minges, H., Voss, H., Feiner, R., Sewald, N.: Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions. CHEMCATCHEM. 8, 1799-1803 (2016).
Frese, Marcel, Schnepel, Christian, Minges, Hannah, Voss, Hauke, Feiner, Rebecca, and Sewald, Norbert. “Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions”. CHEMCATCHEM 8.10 (2016): 1799-1803.
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