134235-82-8

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-;D-7-Azatryptophan;(R)-2-AMino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid;7-Aza-D-tryptophan
• CAS NO: 134235-82-8
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.216
• Mol File: 134235-82-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-(134235-82-8)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-(134235-82-8)

Safety Data

• Hazardous Substances Data: 134235-82-8(Hazardous Substances Data)

Usage

General Description

The chemical compound "1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-" is a chiral molecule, meaning it exists in two mirror-image forms. It belongs to the class of pyrrolopyridine compounds and consists of a pyrrole and pyridine ring fused together with a propanoic acid side chain. The "a-amino" indicates the presence of an amino group at the alpha position of the propanoic acid. 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)- is commonly used as a building block in the synthesis of various pharmaceuticals, particularly in the development of targeted therapies for diseases. Its unique structure and chiral nature make it a valuable tool for drug discovery and medicinal chemistry research.

Upstream product

• 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 
• 5654-92-2 7-azagramine 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 
• 271-63-6 7-Azaindole 
• 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 
• 144657-73-8 tert-butyl α-amino-β-(1-tert-butyloxycarbonyl-7-azaindolyl)propionate 

Relevant articles and documents

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.