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Literature DB >> 30815918

Fluorogenic Diversification of Unprotected Bromotryptophan by Aqueous Mizoroki-Heck Cross-Coupling.

Hendrik Gruß¹, Clara Belu¹, Laura M Bernhard¹, Arne Merschel¹, Norbert Sewald¹.

Abstract

Fluorescent styryl-tryptophans have been synthesized by a Mizoroki-Heck cross-coupling from unprotected bromotryptophan in aqueous medium showing promising spectrophotometric properties for possible application in fluorescence labelling of biomolecules. Moreover, this strategy permits a modular combination of biocatalytic halogenation by using immobilized FAD-dependent tryptophan halogenases and Pd-mediated chemocatalysis in a multistep one-pot process.

Entities: Chemical

Keywords: Mizoroki-Heck cross-coupling; aqueous medium; chemoenzymatic process; fluorescence; halotryptophan

Year: 2019 PMID： 30815918 DOI： 10.1002/chem.201900437

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

8 in total

1. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Authors: Steffen Dachwitz; Bjarne Scharkowski; Norbert Sewald
Journal: Chemistry Date: 2021-11-11 Impact factor: 5.020

2. Heck Diversification of Indole-Based Substrates under Aqueous Conditions: From Indoles to Unprotected Halo-tryptophans and Halo-tryptophans in Natural Product Derivatives.

Authors: Cristina Pubill-Ulldemolins; Sunil V Sharma; Christopher Cartmell; Jinlian Zhao; Paco Cárdenas; Rebecca J M Goss
Journal: Chemistry Date: 2019-07-19 Impact factor: 5.236

3. Size-Dependent Cellular Uptake of RGD Peptides.

Authors: Isabell Kemker; Rebecca C Feiner; Kristian M Müller; Norbert Sewald
Journal: Chembiochem Date: 2019-10-25 Impact factor: 3.164

4. Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.

Authors: Steffen Dachwitz; Dario H Duwe; Yating Hong Wang; Hendrik Gruß; Yvonne Hannappel; Thomas Hellweg; Norbert Sewald
Journal: Chemistry Date: 2020-10-29 Impact factor: 5.236

5. Recombinant l-Amino Acid Oxidase with Broad Substrate Spectrum for Co-substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions.

Authors: Tobias Heinks; Jannik Paulus; Simon Koopmeiners; Tobias Beuel; Norbert Sewald; Matthias Höhne; Uwe T Bornscheuer; Gabriele Fischer von Mollard
Journal: Chembiochem Date: 2022-07-05 Impact factor: 3.461

Fluorogenic Diversification of Unprotected Bromotryptophan by Aqueous Mizoroki-Heck Cross-Coupling.

1. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

2. Heck Diversification of Indole-Based Substrates under Aqueous Conditions: From Indoles to Unprotected Halo-tryptophans and Halo-tryptophans in Natural Product Derivatives.

3. Size-Dependent Cellular Uptake of RGD Peptides.

4. Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.

5. Recombinant l-Amino Acid Oxidase with Broad Substrate Spectrum for Co-substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions.

6. Bromination of L-tryptophan in a Fermentative Process With Corynebacterium glutamicum.

7. Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.

8. Phenothiazine-Biaryl-Containing Fluorescent RGD Peptides.