218.2518 | - Indole Building Blocks

Nakano, Shogo et al. published their research in ACS Catalysis in 2019 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C12H14N2O2

Deracemization and Stereoinversion to Aromatic D-Amino Acid Derivatives with Ancestral L-Amino Acid Oxidase was written by Nakano, Shogo;Minamino, Yuki;Hasebe, Fumihito;Ito, Sohei. And the article was included in ACS Catalysis in 2019.COA of Formula: C12H14N2O2 This article mentions the following:

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 chem. 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 (鈭?0.7 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. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6COA of Formula: C12H14N2O2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Dodani, Sheel C. et al. published their research in ChemBioChem in 2014 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C12H14N2O2

Structural, Functional, and Spectroscopic Characterization of the Substrate Scope of the Novel Nitrating Cytochrome P450 TxtE was written by Dodani, Sheel C.;Cahn, Jackson K. B.;Heinisch, Tillmann;Brinkmann-Chen, Sabine;McIntosh, John A.;Arnold, Frances H.. And the article was included in ChemBioChem in 2014.Electric Literature of C12H14N2O2 This article mentions the following:

A novel cytochrome P 450 enzyme, TxtE, was recently shown to catalyze the direct aromatic nitration of L-tryptophan. This unique chem. inspired us to ask whether TxtE could serve as a platform for engineering new nitration biocatalysts to replace current harsh synthetic methods. As a first step toward this goal, and to better understand the wild-type enzyme, we obtained high-resolution structures of TxtE in its substrate-free and substrate-bound forms. We also screened a library of substrate analogs for spectroscopic indicators of binding and for production of nitrated products. From these results, we found that the wild-type enzyme accepts moderate decoration of the indole ring, but the amino acid moiety is crucial for binding and correct positioning of the substrate and therefore less amenable to modification. A nitrogen atom is essential for catalysis, and a carbonyl must be present to recruit the 伪B’₁ helix of the protein to seal the binding pocket. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6Electric Literature of C12H14N2O2).

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C12H14N2O2

Booth, Elizabeth S. et al. published their research in Journal of Biological Chemistry in 2015 | CAS: 951-55-3

2-Amino-3-(5-methyl-1H-indol-3-yl)propanoic acid (cas: 951-55-3) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.COA of Formula: C12H14N2O2

Substrate Oxidation by Indoleamine 2,3-Dioxygenase was written by Booth, Elizabeth S.;Basran, Jaswir;Lee, Michael;Handa, Sandeep;Raven, Emma L.. And the article was included in Journal of Biological Chemistry in 2015.COA of Formula: C12H14N2O2 This article mentions the following:

The kynurenine pathway is the major route of L-tryptophan (L-Trp) catabolism in biol., leading ultimately to the formation of NAD⁺. The initial and rate-limiting step of the kynurenine pathway involves oxidation of L-Trp to N-formylkynurenine (NFK). This is an O₂-dependent process and catalyzed by indoleamine 2,3-dioxygenase (IDO) and tryptophan 2,3-dioxygenase (TDO). More than 60 years after these dioxygenase enzymes were first isolated (Kotake, Y., and Masayama, I. (1936) Z. Physiol. Chem. 243, 237-244), the mechanism of the reaction is not established. We examined the mechanism of substrate oxidation for a series of substituted tryptophan analogs by indoleamine 2,3-dioxygenase. We observed formation of a transient intermediate, assigned as a Compound II (ferryl) species, during oxidation of L-Trp, 1-methyl-L-Trp, and a number of other substrate analogs. The data are consistent with a common reaction mechanism for indoleamine 2,3-dioxygenase-catalyzed oxidation of tryptophan and other tryptophan analogs. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(5-methyl-1H-indol-3-yl)propanoic acid (cas: 951-55-3COA of Formula: C12H14N2O2).

Lepri, Luciano et al. published their research in Journal of Planar Chromatography–Modern TLC in 1992 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Formula: C12H14N2O2

Reversed phase planar chromatography of enantiomeric tryptophans with bovine serum albumin in the mobile phase was written by Lepri, Luciano;Coas, Vanda;Desideri, Pier Giorgio;Zocchi, Andrea. And the article was included in Journal of Planar Chromatography–Modern TLC in 1992.Formula: C12H14N2O2 This article mentions the following:

The chromatog. behavior of racemic tryptophan, tryptophanamide, glycyltryptophan, and eight substituted tryptophans on several types of reversed phase layers developed with aqueous organic solutions containing high amounts of bovine serum albumin (BSA) has been extensively investigated. The resolution of the enantiomers is highly dependent on the apparent pH of the eluent; in particular, the best conditions for their resolution have been obtained in the pH range 9-10. The amount of 2-propanol in the mobile phase also plays an important role, as does the type of layer; some of the octadecyl layers, for example, could not be used with an eluent pH higher than 9.55. The 伪 and R_s values of the different enantiomers are generally higher than those achieved on microcrystalline cellulose. BSA in the mobile phase can be successfully employed for the separation of a large number of racemic compounds In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6Formula: C12H14N2O2).

Nakano, Shogo et al. published their research in ACS Catalysis in 2019 | CAS: 17332-70-6

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 chem. 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. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6COA of Formula: C12H14N2O2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Dodani, Sheel C. et al. published their research in ChemBioChem in 2014 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C12H14N2O2

A novel cytochrome P 450 enzyme, TxtE, was recently shown to catalyze the direct aromatic nitration of L-tryptophan. This unique chem. inspired us to ask whether TxtE could serve as a platform for engineering new nitration biocatalysts to replace current harsh synthetic methods. As a first step toward this goal, and to better understand the wild-type enzyme, we obtained high-resolution structures of TxtE in its substrate-free and substrate-bound forms. We also screened a library of substrate analogs for spectroscopic indicators of binding and for production of nitrated products. From these results, we found that the wild-type enzyme accepts moderate decoration of the indole ring, but the amino acid moiety is crucial for binding and correct positioning of the substrate and therefore less amenable to modification. A nitrogen atom is essential for catalysis, and a carbonyl must be present to recruit the αB’₁ helix of the protein to seal the binding pocket. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6Electric Literature of C12H14N2O2).

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C12H14N2O2

Booth, Elizabeth S. et al. published their research in Journal of Biological Chemistry in 2015 | CAS: 951-55-3

Lepri, Luciano et al. published their research in Journal of Planar Chromatography–Modern TLC in 1992 | CAS: 17332-70-6

The chromatog. behavior of racemic tryptophan, tryptophanamide, glycyltryptophan, and eight substituted tryptophans on several types of reversed phase layers developed with aqueous organic solutions containing high amounts of bovine serum albumin (BSA) has been extensively investigated. The resolution of the enantiomers is highly dependent on the apparent pH of the eluent; in particular, the best conditions for their resolution have been obtained in the pH range 9-10. The amount of 2-propanol in the mobile phase also plays an important role, as does the type of layer; some of the octadecyl layers, for example, could not be used with an eluent pH higher than 9.55. The α and R_s values of the different enantiomers are generally higher than those achieved on microcrystalline cellulose. BSA in the mobile phase can be successfully employed for the separation of a large number of racemic compounds In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6Formula: C12H14N2O2).