(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate
• CAS No.: 73-22-3
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.228
• Hs Code.: 2933990090
• Mol file: 73-22-3.mol

Synonyms:2-amino-3-indolylpropanic acid;(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;3rzi;L-tryptophan zwitterion;3f3a;3qs4;3qs5;3qs6;SCHEMBL23141133;CHEBI:57912;(2S)-2-ammonio-3-(1H-indol-3-yl)propanoate

Chemical Property of (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 8.3E-09mmHg at 25°C
• Melting Point: 289-290 °C (dec.)(lit.)
• Refractive Index: -32 ° (C=1, H2O)
• Boiling Point: 447.908 °C at 760 mmHg
• Flash Point: 224.687 °C
• PSA: 79.11000
• Density: 1.363 g/cm³
• LogP: 1.82260
• Water Solubility.: 11.4 g/L (25℃)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: R33:有累积作用的危险‖R40
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)[O-])[NH3+]
• Essential Amino Acid: Tryptophan (TRP) is an essential amino acid in mammals, crucial for various physiological processes such as neuronal function, immunity, and gut homeostasis.
• Chemical Structure and Classification: Tryptophan is the largest of the three aromatic amino acids, with a benzoic nucleus and a pyrrole ring in its side chain. It has the molecular formula C11H12N2O2 and is categorized as a glucogenic/ketogenic amino acid.
• Dietary Sources and Absorption: Being essential, TRP must be obtained through the diet. Rich dietary sources include dairy products, eggs, meat, fish, and chocolate. After being released from dietary protein, TRP is absorbed through the intestinal epithelium into the systemic circulation, where intestinal microbiota further metabolizes it to indoles.
• Physiological Effects: TRP serves as a precursor for metabolites that significantly affect various physiological functions, including gastrointestinal functions, immunity, metabolism, and the nervous system.
• Binding and Regulation: In circulation, TRP is primarily bound to albumin, with only a small fraction being free. Plasma TRP levels are regulated by factors such as glucocorticoids, interferon-纬, glucose, nicotinamide, and antidepressants.
• Implications in Neuropsychiatric and Neurodegenerative Disorders: Changes in circulating TRP levels can impact its availability for serotonin and melatonin synthesis in the brain, potentially contributing to the pathophysiology of various neuropsychiatric and neurodegenerative disorders.
• Role in Cancer and Immunoregulation: TRP metabolism has been implicated in cancer-related processes, including anti-proliferative effects on tumor cells and cancer-related anorexia and cachexia. Research is ongoing regarding the immunoregulatory properties of IDO and its involvement in diseases such as autoimmunity, infection, and cancer.

Technology Process of (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

There total 159 articles about (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-{(4-{methyl[(4-nitrophenoxy)carbonyl]amino}benzyloxy)carbonyl}-L-tryptophan (402943-23-1) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + carbon dioxide (124-38-9,18923-20-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + (4-(methylamino)phenyl)methanol (181819-75-0)

Guidance literature:

With abzyme ST₅₁; water; In dimethyl sulfoxide; at 25 ℃; pH=9.0; Further Variations:; time dependence; Enzyme kinetics;

DOI:10.1039/b103971g

Reference yield:

water (7732-18-5) + [5']adenylic acid L-tryptophan anhydride (31528-64-0) → 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

at 37 ℃; Zeitlicher Verlauf in Loesung vom pH 7.2.Hydrolysis;

Reference yield:

secretory phospholipase A2 from Crotalus durissus cascavella venom modified with naringin → L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-Cysteine (52-90-4) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With hydrogenchloride; phenol; In water; at 106 ℃; for 24h;

DOI:10.3390/molecules16010738

upstream raw materials:

indole

L-serin

L-Aspartic acid

Indole-3-pyruvic acid

Downstream raw materials:

L-tryptophan methyl ester

3-carboxy-1,2,3,4-tetrahydro-2-carboline

(2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoic acid

L-tryptophan ethyl ester

Refernces

• 1、 Bunn, Brittney M,Xu, Mizhi,Webb, Chase M,Viswanathan, Rajesh. "Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA". . . Retrieved 2021/04/26.
• 2、 -. "COMPOUNDS AND METHODS FOR SELECTIVE C-TERMINAL LABELING". Paragraph 0033; 0230. . Retrieved 2021/07/24.