Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins

Abstract

A boron and nitrogen containing unnatural analogue of tryptophan is synthesized and incorporated into proteins.

Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer

“…The strategy, which exploits an evolved TrpB synthase, 11 marks a significant improvement over conventional synthetic methods for unnatural L-Trp derivatives that require multiple steps and are associated with low yields. 12,13 While 5HOW is expected to have different electrostatic properties than Trp (see Fig. S1), incorporation of 5HOW into different proteins has been performed using human and E. coli expression systems without significant deleterious effects on protein structure or function.…”

Reprogramming natural proteins using unnatural amino acids

“…5b ). 48 More notably, these studies demonstrated the first example of an azaborine containing amino acid being introduced into proteins.…”

“…Therefore, an extensive study on enantioselective, catalytic, and chiral pool synthesis of optically pure UAAs has been reported in recent years. [43][44][45][46][47][48][49][50][51] Further study in the design of novel catalysts and chiral auxiliaries, as well as proper selection of chiral precursors for chiral pool synthesis, could enhance the synthesis of chiral UAAs with an excellent enantiomeric excess (ee) and high yield. Consideration of the green chemistry approach towards the asymmetric synthesis of UAAs is highly recommended.…”

An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides

“…[2] They also play an important role in organic synthesis, catalysis, and biochemistry. [5] In addition, since the BÀ N unit has a strong dipole moment, replacing the C=C with a BÀ N unit can reduce the HOMO-LUMO gap, which usually results in a chemiluminescent material. [5] In addition, since the BÀ N unit has a strong dipole moment, replacing the C=C with a BÀ N unit can reduce the HOMO-LUMO gap, which usually results in a chemiluminescent material.…”

“…[3] Furthermore, boron-containing N-heterocyclic compounds with valuable BÀ N structural units exhibited useful behavior in materials and biomedical research as fluorescent dyes [4] and biological labeling. [5] In addition, since the BÀ N unit has a strong dipole moment, replacing the C=C with a BÀ N unit can reduce the HOMO-LUMO gap, which usually results in a chemiluminescent material. [6] As one of the major classes of valuable boron-containing heterocyclic compounds, 1,3,2-benzodiazaborininones have high stability toward moisture, oxygen, and even silica gel chromatography.…”