134235-82-8

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)is used as a key building block for the synthesis of various pharmaceuticals, leveraging its unique structure and chiral properties to develop targeted therapies for a range of diseases. Its incorporation into drug molecules allows for enhanced selectivity and efficacy in treating specific conditions.
Used in Drug Discovery:
In the field of drug discovery, 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)serves as a valuable tool for designing and optimizing novel drug candidates. Its unique structural features and chiral nature enable researchers to explore a wide range of chemical modifications and interactions with biological targets, thereby accelerating the identification of potential therapeutic agents.
Used in Medicinal Chemistry Research:
1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)is employed in medicinal chemistry research to investigate the structure-activity relationships of drug molecules. Its distinctive molecular framework and chiral properties provide a solid foundation for understanding the relationship between molecular structure and biological activity, facilitating the design of more effective and selective therapeutic agents.

Upstream product

• 144657-73-8 tert-butyl α-amino-β-(1-tert-butyloxycarbonyl-7-azaindolyl)propionate 
• 271-63-6 7-Azaindole 
• 5654-92-2 7-azagramine 
• 7303-50-6 7-azatryptophan 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 144657-72-7 3-{(R)-2-tert-Butoxycarbonyl-2-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-ethyl}-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 
• 144657-70-5 1-(tert-butyloxycarbonyl)-3-(iodomethyl)-7-azaindole 
• 144657-69-2 1-(tert-butyloxycarbonyl)-3-(bromomethyl)-7-azaindole 
• 144657-68-1 tert-butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 
• 144657-67-0 tert-butyl 3-(hydroxymethyl)-1 H-pyrrolo[2,3-b]pyridine-1-carboxylate 
• 144657-66-9 tert-butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 
• 63024-18-0 N^α-Acetyl-DL-7-azatryptophan 
• 211179-97-4 diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate 

Relevant academic research and scientific papers

Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase

Enantiomerically pure amino acid derivatives could be foundational compounds for peptide drugs. Deracemization of racemates to l-amino acid derivatives can be achieved through the reaction of evolved d-amino acid oxidase and chemical reductants, whereas deracemization to d-amino acid derivatives has not progressed due to the difficulty associated with the heterologous expression of l-amino acid oxidase (LAAO). In this study, we succeeded in developing an ancestral LAAO (AncLAAO) bearing broad substrate selectivity (13 l-amino acids) and high productivity through an Escherichia coli expression system (50.7 mg/L). AncLAAO can be applied to perform deracemization to d-amino acids in a similar way to deracemization to l-amino acids. In fact, full conversion (>99% ee, d-form) could be achieved for 16 racemates, including nine d,l-Phe derivatives, six d,l-Trp derivatives, and a d,l-phenylglycine. Taken together, we believe that AncLAAO could be a key enzyme to obtain optically pure d-amino acid derivatives in the future.

Chemoenzymatic synthesis of the two enantiomers of 7-azatryptophan

7-Azatryptophan is an unnatural α-amino acid with a very potent fluorescent activity. It is used as a vehicle for probing the structure and dynamics of proteins and peptides. Diastereoselective alkylation, diastereoselective protonation and enzymatic resolution have been tested for preparing enantiomerically pure 7-azatryptophan.

Syntheses of a potential fluorescence probe, (-)-(R)-7-azatryptophan, via alkylation of the (1R,4R)-camphor imine of tert-butylglycinate

The synthesis of (-)-(R)-7-azatryptophan (2) from commercially available 7-azaindole (4) is described.The key step involved the diastereoselective alkylation of tert-butyl acetate (3) with 1-(tert-butyloxycarbonyl-3-(iodomethyl)-7-azaindole (14).The alkylation, conducted at -100 deg C in a THF/HMPA solvent using potassium hexamethyldisilazide as the base, afforded 7 in a greater than 98 percent diastereomeric excess.Hydrolysis and deprotecting gave (-)-(R)-7-azatryptophan.