608535-19-9

Upstream product

• 3705-42-8 Cbz-(L)-Glu-OBn 
• 37517-78-5 magnesium bis(3-ethoxy-3-oxopropanoate) 
• 6148-64-7 ethyl potassium malonate 

Downstream Products

• 905442-42-4 L-2-((7-hydroxycoumarin-4-yl)-ethane-2-yl)glycine 

Relevant academic research and scientific papers

Site-specific analysis of protein hydration based on unnatural amino acid fluorescence

Hydration of proteins profoundly affects their functions. We describe a simple and general method for site-specific analysis of protein hydration based on the in vivo incorporation of fluorescent unnatural amino acids and their analysis by steady-state fl

A concise preparation of the fluorescent amino acid L-(7-hydroxycoumarin-4- yl) ethylglycine and extension of its utility in solid phase peptide synthesis

Incorporation of the unnatural amino acid L-(7-hydroxycoumarin-4-yl) ethylglycine (7-HC) is a powerful and reliable approach for the preparation of fluorescently labeled proteins. The growing popularity of this valuable amino acid prompted us to pursue an

An alternative route to the proline derivative (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid from protected glutamic acid

The synthesis of (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid was achieved in two steps, with an overall yield of 53%. This synthesis used Cbz-Glu-OBzl as the starting material and led to the titled compound with a d.e.>96%.

Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids

Incorporation of the fluorogenic l-(7-hydroxycoumarin-4-yl)ethylglycine into proteins is a valuable biological tool. Coumarins are typically accessed via the Pechmann reaction, which requires acidic conditions and lacks substrate flexibility. A Pd-mediated coupling is described between o-methoxyboronic acids and a glutamic acid derived (Z)-vinyl triflate, forming latent coumarins. Global deprotection with BBr3 forms the coumarin scaffold in a single step. This mild and scalable route yielded five analogues, including a probe suitable for use at lower pH.

Fluorescent IGF-II analogues for FRET-based investigations into the binding of IGF-II to the IGF-1R

The interaction of IGF-II with the insulin receptor (IR) and type 1 insulin-like growth factor receptor (IGF-1R) has recently been identified as potential therapeutic target for the treatment of cancer. Understanding the interactions of IGF-II with these receptors is required for the development of potential anticancer therapeutics. This work describes an efficient convergent synthesis of native IGF-II and two non-native IGF-II analogues with coumarin fluorescent probes incorporated at residues 19 and 28. These fluorescent analogues bind with nanomolar affinities to the IGF-1R and are suitable for use in fluorescence resonance energy transfer (FRET) studies. From these studies the F19Cou IGF-II and F28Cou IGF-II proteins were identified as good probes for investigating the binding interactions of IGF-II with the IGF-1R and its other high affinity binding partners.

HIGH-SENSITIVE FLUORESCENT ENERGY TRANSFER ASSAY USING FLUORESCENT AMINO ACIDS AND FLUORESENT PROTEINS

The disclosure provides method and composition utilizing fluorescent amino acids and fluorescent proteins comprising a moiety capable of undergoing FRET. The methods and compositions of the disclosure are useful in analyzing protein structure and function

Biosynthesis of a fluorescent protein with extreme Pseudo-stokes shift by introducing a genetically encoded non-natural amino acid outside the fluorophore

A novel kind of fluorescent protein relying on the intramolecular interplay between two different fluorophores, one of chemical origin and one of biological origin, was developed. The fluorescent non-natural amino acid l-(7-hydroxycoumarin-4-yl)ethylglyci

Genetically encoded fluorescent coumarin amino acids

The invention relates to orthogonal pairs of tRNAs and aminoacyl-tRNA synthetases that can incorporate the coumarin unnatural amino acid L-(7-hydroxycoumarin-4-yl) ethylglycine into proteins produced in eubacterial host cells such as E. coli. The invention provides, for example but not limited to, novel orthogonal synthetases, methods for identifying and making the novel synthetases, methods for producing proteins containing the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine and related translation systems.

A genetically encoded fluorescent amino acid

The fluorescent amino acid l-(7-hydroxycoumarin-4-yl) ethylglycine 1 has been genetically encoded in E. coli in response to the amber TAG codon. Because of its high fluorescence quantum yield, relatively large Stoke's shift, and sensitivity to both pH and

A method for manufacturing optically active coumaryl amino acid salts and the coumaryl aminoacid salts thus obtained

The present invention relates to the field of the synthesis of optically active amino acids, mainly for the purpose of manufacturing optically active polypeptides that are useful as labelled detection tools. The manufacturing method involves the preparati