49758-35-2

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)-;L-7-Azatryptophan;1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-aMino-, (S)-;(S)-2-aMino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid;3-(1H-Pyrrolo[2,3-b]Pyridin-3-Yl)Alanine;(S)-2-ammonio-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate;(2S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid;(aS)-a-amino-1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid
• CAS NO: 49758-35-2
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.216
• Mol File: 49758-35-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)-(49758-35-2)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)-(49758-35-2)

Safety Data

• Hazardous Substances Data: 49758-35-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)is used as a potential pharmaceutical compound for its unique structure and functional groups, which may contribute to the development of new drugs or therapeutic agents.
Used in Biochemical Research:
In the field of biochemistry, 1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aS)may serve as a research tool or a building block for the synthesis of more complex molecules, given its distinct chemical features and chiral nature.

Upstream product

• 7303-50-6 7-azatryptophan 
• 271-63-6 7-Azaindole 
• 56-45-1 L-serin 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 211179-97-4 diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate 
• 63024-18-0 N^α-Acetyl-DL-7-azatryptophan 

Downstream Products

• 1200129-86-7 C₂₂H₂₁N₅O₂ 
• 1200129-93-6 C₂₂H₂₂N₆O 
• 1200127-66-7 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile 
• 4649-12-1 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethylamine 

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.

Directed evolution of the tryptophan synthase β-subunit for stand-alone function recapitulates allosteric activation

Enzymes in heteromeric, allosterically regulated complexes catalyze a rich array of chemical reactions. Separating the subunits of such complexes, however, often severely attenuates their catalytic activities, because they can no longer be activated by their protein partners. We used directed evolution to explore allosteric regulation as a source of latent catalytic potential using the β-subunit of tryptophan synthase from Pyrococcus furiosus (PfTrpB). As part of its native αββα complex, TrpB efficiently produces tryptophan and tryptophan analogs; activity drops considerably when it is used as a stand-alone catalyst without the α-subunit. Kinetic, spectroscopic, and X-ray crystallographic data show that this lost activity can be recovered by mutations that reproduce the effects of complexation with the α-subunit. The engineered PfTrpB is a powerful platform for production of Trp analogs and for further directed evolution to expand substrate and reaction scope.

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.