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(S)-2-amino-3-(1H-indole-3-yl)-N-phenylpropionamide, also known as L-tryptophan amide or α-methyltryptophan amide, is a complex chemical compound that belongs to the amino acid group. It is a chiral molecule with an amine and a carboxylic acid functional group, as well as a phenyl and an indole group. (S)-2-amino-3-(1H-indole-3-yl)-N-phenylpropionamide plays a crucial role in the biosynthesis of proteins, neurotransmitters, and other biologically active molecules in living organisms.

127592-76-1

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127592-76-1 Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-amino-3-(1H-indole-3-yl)-N-phenylpropionamide is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Biochemical Research:
In the field of biochemistry, (S)-2-amino-3-(1H-indole-3-yl)-N-phenylpropionamide serves as an important research tool for studying the mechanisms of protein synthesis, enzyme catalysis, and other biological processes. Its involvement in the biosynthesis of neurotransmitters also makes it a valuable compound for investigating the role of these molecules in the nervous system.
Used in Agrochemical Industry:
(S)-2-amino-3-(1H-indole-3-yl)-N-phenylpropionamide has potential applications in the agrochemical industry, where it can be utilized as a precursor for the synthesis of bioactive molecules with pesticidal, herbicidal, or plant growth-regulating properties. Its unique structure and functional groups make it a promising candidate for the development of novel agrochemicals with improved efficacy and selectivity.

Check Digit Verification of cas no

The CAS Registry Mumber 127592-76-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,7,5,9 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 127592-76:
(8*1)+(7*2)+(6*7)+(5*5)+(4*9)+(3*2)+(2*7)+(1*6)=151
151 % 10 = 1
So 127592-76-1 is a valid CAS Registry Number.

127592-76-1Relevant articles and documents

Synthetic process of chiral N-aromatic amino acid amide

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Paragraph 0010; 0014, (2016/10/17)

Chiral N-aromatic amino acid amide is a core structure fragment of drugs and an intermediate of the drugs. Only if the chiral structure of the product is not required by special raw materials such aryl halide activated by functional groups of nitryl and t

Tryptophan derivative, preparing method and application in preventing and treating plant viruses, killing bacteria and killing insects

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Paragraph 0098; 0099; 0100; 0101, (2017/06/02)

The invention relates to a tryptophan derivative (I), a preparing method of the tryptophan derivative (I), and application of the tryptophan derivative (I) in preventing and treating plant viruses, killing bacteria and killing insects. The formula of the tryptophan derivative (I) is shown in the description, and the meanings of all groups in the formula are shown in the description. The tryptophan derivative expresses especially excellent plant virus resisting activity, and also has broad-spectrum bactericidal activity and insecticidal activity.

C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids

Huang, Yuanqiong,Liu, Yongxian,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin

, p. 462 - 473 (2016/01/25)

According to our previous work and the latest research on the biosynthesis of β-carboline, and using the reverse thinking strategy, tryptophan, the biosynthesis precursor of β-carboline alkaloids, and their derivatives were synthesized, and their biological activities and structure-activity relationships were studied. This bioassay showed that these compounds exhibited good inhibitory activities against tobacco mosaic virus (TMV); especially (S)-2-amino-3-(1H-indol-3-yl)-N-octylpropanamide (4) (63.3 ± 2.1%, 67.1 ± 1.9%, 68.7 ± 1.3%, and 64.5 ± 3.1%, 500 μg/mL) exhibited the best antiviral activity both in vitro and in vivo. Compound 4 was chosen for the field trials and the acute oral toxicity test, the results showed that the compound exhibited good anti-TMV activity in the field and low acute oral toxicity. We also found that these compounds showed antifungal activities and insecticidal activities.

Virtual screening of peptide and peptidomimetic fragments targeted to inhibit bacterial dithiol oxidase DsbA

Duprez, Wilko,Bachu, Prabhakar,Stoermer, Martin J.,Tay, Stephanie,McMahon, Róisín M.,Fairlie, David P.,Martin, Jennifer L.

, (2015/10/05)

Antibacterial drugs with novel scaffolds and new mechanisms of action are desperately needed to address the growing problem of antibiotic resistance. The periplasmic oxidative folding system in Gram-negative bacteria represents a possible target for anti-virulence antibacterials. By targeting virulence rather than viability, development of resistance and side effects (through killing host native microbiota) might be minimized. Here, we undertook the design of peptidomimetic inhibitors targeting the interaction between the two key enzymes of oxidative folding, DsbA and DsbB, with the ultimate goal of preventing virulence factor assembly. Structures of DsbB - or peptides - complexed with DsbA revealed key interactions with the DsbA active site cysteine, and with a hydrophobic groove adjacent to the active site. The present work aimed to discover peptidomimetics that target the hydrophobic groove to generate non-covalent DsbA inhibitors. The previously reported structure of a Proteus mirabilis DsbA active site cysteine mutant, in a non-covalent complex with the heptapeptide PWATCDS, was used as an in silico template for virtual screening of a peptidomimetic fragment library. The highest scoring fragment compound and nine derivatives were synthesized and evaluated for DsbA binding and inhibition. These experiments discovered peptidomimetic fragments with inhibitory activity at millimolar concentrations. Although only weakly potent relative to larger covalent peptide inhibitors that interact through the active site cysteine, these fragments offer new opportunities as templates to build non-covalent inhibitors. The results suggest that non-covalent peptidomimetics may need to interact with sites beyond the hydrophobic groove in order to produce potent DsbA inhibitors.

Organocatalysis of asymmetric aldol reaction in water: Comparison of catalytic properties of (S)-valine and (S)-proline amides

Kucherenko,Siyutkin,Dashkin,Zlotin

, p. 1010 - 1015 (2014/03/21)

(S)-Valine amides containing (S)- or (R)-α-phenylethyl substituents at N1 atom efficiently catalyze asymmetric aldol reactions between cyclic (heterocyclic) ketones and aromatic aldehydes in water, predominantly giving rise to the aldol anti-di

CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME

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Page/Page column 10; 21, (2012/06/16)

The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

Linear TMC-95-based proteasome inhibitors

Basse, Nicolas,Piguel, Sandrine,Papapostolou, David,Ferrier-Berthelot, Alexandra,Richy, Nicolas,Pagano, Maurice,Sarthou, Pierre,Sobczak-Thépot, Jo?lle,Reboud-Ravaux, Michele,Vidal, Jo?lle

, p. 2842 - 2850 (2008/02/07)

We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and

COMPOUNDS USEFUL AS MODULATORS OF THE PROTEASOME ACTIVITY

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Page/Page column 36, (2008/06/13)

The present invention relates to the use of compounds of the following general formula (I): wherein no is 0 or 1, and when no is 1, X = CH2 or X = NCH2C6H5; R1 is OH, or a OR10 group, or a group of formula NH-(CH2)n1-R11; R2 is H, or an alkyl group, or a group of formula (CH2)n2-(CO)n3-NR13R14; R3 is H, or an alkyl group; R4 is H, or Boc, or Z; R5 is H, or Boc, or Z ; R6 is a OR16 group; R7 and R8 are H, or a halogen atom, as modulators of the proteasome activity, in the frame of the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, or the preparation of cosmetic compositions, or of phytosanitary compositions.

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