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Literature DB >> 32452506

Modular control of l-tryptophan isotopic substitution via an efficient biosynthetic cascade.

Clayton M Thompson¹, Allwin D McDonald¹, Hanming Yang¹, Silvia Cavagnero¹, Andrew R Buller¹.

Abstract

Isotopologs are powerful tools for investigating biological systems. We report a biosynthetic-cascade synthesis of Trp isotopologs starting from indole, glycine, and formaldehyde using the enzymes l-threonine aldolase and an engineered β-subunit of tryptophan synthase. This modular route to Trp isotopologs is simple and inexpensive, enabling facile access to these compounds.

Entities: Chemical Disease Species

Year: 2020 PMID： 32452506 PMCID： PMC7418710 DOI： 10.1039/d0ob00868k

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

17 in total

1. Stereochemistry and mechanism of reactions catalyzed by tryptophan synthetase and its beta2 subunit.

Authors: M D Tsai; E Schleicher; R Potts; G E Skye; H G Floss
Journal: J Biol Chem Date: 1978-08-10 Impact factor: 5.157

2. Enzymatic assembly of DNA molecules up to several hundred kilobases.

Authors: Daniel G Gibson; Lei Young; Ray-Yuan Chuang; J Craig Venter; Clyde A Hutchison; Hamilton O Smith
Journal: Nat Methods Date: 2009-04-12 Impact factor: 28.547

3. Synthesis of β-Branched Tryptophan Analogues Using an Engineered Subunit of Tryptophan Synthase.

Authors: Michael Herger; Paul van Roye; David K Romney; Sabine Brinkmann-Chen; Andrew R Buller; Frances H Arnold
Journal: J Am Chem Soc Date: 2016-07-01 Impact factor: 15.419

Review 4. Biosynthetic manipulation of tryptophan in bacteria: pathways and mechanisms.

Authors: Lona M Alkhalaf; Katherine S Ryan
Journal: Chem Biol Date: 2015-03-19

5. Attenuated T2 relaxation by mutual cancellation of dipole-dipole coupling and chemical shift anisotropy indicates an avenue to NMR structures of very large biological macromolecules in solution.

Authors: K Pervushin; R Riek; G Wider; K Wüthrich
Journal: Proc Natl Acad Sci U S A Date: 1997-11-11 Impact factor: 11.205

Review 10. Threonine aldolases: perspectives in engineering and screening the enzymes with enhanced substrate and stereo specificities.

Authors: Kateryna Fesko
Journal: Appl Microbiol Biotechnol Date: 2016-01-26 Impact factor: 4.813

1 in total

1. Selective Isotope Labeling and LC-Photo-CIDNP Enable NMR Spectroscopy at Low-Nanomolar Concentration.

Authors: Hanming Yang; Siyu Li; Clayton A Mickles; Valeria Guzman-Luna; Kenji Sugisaki; Clayton M Thompson; Hung H Dang; Silvia Cavagnero
Journal: J Am Chem Soc Date: 2022-06-14 Impact factor: 16.383

1 in total

Modular control of l-tryptophan isotopic substitution via an efficient biosynthetic cascade.

1. Stereochemistry and mechanism of reactions catalyzed by tryptophan synthetase and its beta2 subunit.

2. Enzymatic assembly of DNA molecules up to several hundred kilobases.

3. Synthesis of β-Branched Tryptophan Analogues Using an Engineered Subunit of Tryptophan Synthase.

Review 4. Biosynthetic manipulation of tryptophan in bacteria: pathways and mechanisms.

5. Attenuated T2 relaxation by mutual cancellation of dipole-dipole coupling and chemical shift anisotropy indicates an avenue to NMR structures of very large biological macromolecules in solution.

6. Directed Evolution Mimics Allosteric Activation by Stepwise Tuning of the Conformational Ensemble.

7. Directed evolution of the tryptophan synthase β-subunit for stand-alone function recapitulates allosteric activation.

8. Unlocking Reactivity of TrpB: A General Biocatalytic Platform for Synthesis of Tryptophan Analogues.

9. Scaleable catalytic asymmetric Strecker syntheses of unnatural alpha-amino acids.

Review 10. Threonine aldolases: perspectives in engineering and screening the enzymes with enhanced substrate and stereo specificities.

1. Selective Isotope Labeling and LC-Photo-CIDNP Enable NMR Spectroscopy at Low-Nanomolar Concentration.