93102-93-3

Upstream product

• 89205-01-6 5-(4-Methoxy-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 32721-60-1 erythro-β-p-Anisyl-N-benzoylserinmethylester 
• 93103-06-1 2-Mercapto-5-(4-methoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and evaluation of a library of fluorescent dipeptidomimetic analogues as substrates for modified bacterial ribosomes

Described herein are the synthesis and photophysical characterization of a library of aryl-substituted oxazole- and thiazole-based dipeptidomimetic analogues, and their incorporation into position 66 of green fluorescent protein (GFP) in lieu of the natural fluorophore. These fluorescent analogues resemble the fluorophore formed naturally by GFP. As anticipated, the photophysical properties of the analogues varied as a function of the substituents at the para position of the phenyl ring. The fluorescence emission wavelength maxima of compounds in the library varied from ～365 nm (near-UV region) to ～490 nm (visible region). The compounds also exhibited a large range of quantum yields (0.01-0.92). The analogues were used to activate a suppressor tRNACUA and were incorporated into position 66 of GFP using an in vitro protein biosynthesizing system that employed engineered ribosomes selected for their ability to incorporate dipeptides. Four analogues with interesting photophysical properties and reasonable suppression yields were chosen, and the fluorescent proteins (FPs) containing these fluorophores were prepared on a larger scale for more detailed study. When the FPs were compared with the respective aminoacyl-tRNAs and the actual dipeptide analogues, the FPs exhibited significantly enhanced fluorescence intensities at the same concentrations. Part of this was shown to be due to the presence of the fluorophores as an intrinsic element of the protein backbone. There were also characteristic shifts in the emission maxima, indicating the environmental sensitivity of these probes. Acridon-2-ylalanine and oxazole 1a were incorporated into positions 39 and 66 of GFP, respectively, and were shown to form an efficient F?rster resonance energy transfer (FRET) pair, demonstrating that the analogues can be used as FRET probes.

Rhodium-mediated asymmetric transfer hydrogenation: A diastereo- and enantioselective synthesis of: Syn -α-amido β-hydroxy esters

The preparation of syn α-benzoylamido β-hydroxy esters through asymmetric transfer hydrogenation (ATH) with a tethered Rh(iii)-DPEN complex via dynamic kinetic resolution (DKR) has been developed for the first time starting from α-benzoylamido β-keto esters. A variety of α-benzoylamido β-keto esters were converted under mild conditions into the corresponding syn α-benzoylamino β-hydroxy esters with high yields (up to 98%) and diastereomeric ratios (up to >99:1 dr) as well as excellent enantioselectivities (up to >99% ee).

RIBOSOME-MEDIATED INCORPORATION OF PEPTIDES AND PEPTIDOMIMETICS

Modified ribosomes that were selected using a dipeptidyl-puromycin aminonucleoside are used to mediate site-specific incorporation of one or more peptides and peptidomimetics into protein in a cell free translation system. In addition, new fluorescent dipeptidomimetics have been synthesized and incorporated into proteins, as well as modified proteins containing one or more non-naturally occurring dipeptides.