1-Methyl-D-tryptophan

Base Information

• Chemical Name: 1-Methyl-D-tryptophan
• CAS No.: 110117-83-4
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• Mol file: 110117-83-4.mol

Synonyms:(R)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid;D-(+)-1-Methyltryptophan;D-1-Methyltryptophan;D-Tryptophan, 1-methyl-;1-Methyl-D-tryptophane;

Chemical Property of 1-Methyl-D-tryptophan

Chemical Property:

• Vapor Pressure: 3.92E-08mmHg at 25°C
• Melting Point: 242-245 °C(lit.)
• Refractive Index: 1.625
• Boiling Point: 429.3 °C at 760 mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 213.4 °C
• PSA: 68.25000
• Density: 1.28 g/cm³
• LogP: 1.83300
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO (greater than 25 mg/ml).

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Methyl-D-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.
• Uses: Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture. 1-Methyl-D-tryptophan is used in biological studies to determine the effect of IDO2 enzyme (indoleamine-(2,3)-dioxygenase) activity and IDO2-mediated arrest of human T cell proliferation. It reverses IDO-mediated immune suppression

Technology Process of 1-Methyl-D-tryptophan

There total 11 articles about 1-Methyl-D-tryptophan 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: 92.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + methyl iodide (74-88-4) → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

L-Tryptophan; With iron(III) nitrate monohydrate; ammonia; sodium; at -60 ℃;

methyl iodide; In diethyl ether;

DOI:10.1021/jo802216z

Reference yield: 85.0%

N-tert-butyloxycarbonyl-L-1-methyltryptophan methyl ester → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 5h;

Reference yield:

Nα-(tert-butoxycarbonyl)-1-methyl-D-tryptophan (103943-63-1) → D-(+)-Na-methyltryptophan (110117-83-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h;

DOI:10.1016/j.ejmech.2017.05.053

upstream raw materials:

L-Tryptophan

methyl iodide

1-methylindole

L-serin

Downstream raw materials:

Fmoc-1-Me-Trp-OH

tert-butyl [(2R)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexa-hydrophthalazin-2(1H)-yl]piperidin-1-yl}-3-(1-methyl-1H-indol-3-yl)-1-oxopropan-2-yl]carbamate

Refernces

• 1、 -. "Method for synthesizing 1 - methyl - L L-tryptophan (by machine translation)". Paragraph 0008; 0009. . Retrieved 2020/08/02.
• 2、 -. "1-methyl tryptophan synthesis method". Paragraph 0047; 0048; 0049. . Retrieved 2016/10/10.