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452483

Sigma-Aldrich

1-Methyl-D-tryptophan

95%, for peptide synthesis

Synonym(s):

(2R)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid, D-(+)-1-Methyltryptophan

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250 MG
€44.40
1 G
€130.00
10 G
€905.00

€44.40


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250 MG
€44.40
1 G
€130.00
10 G
€905.00

About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
Molecular Weight:
218.25
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

€44.40


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Product Name

1-Methyl-D-tryptophan, 95%

Quality Level

Assay

95%

form

lumps and powder

optical activity

[α]22/D +12.4°, c = 2 in acetic acid

reaction suitability

reaction type: solution phase peptide synthesis

mp

242-245 °C (lit.)

application(s)

peptide synthesis

SMILES string

Cn1cc(C[C@@H](N)C(O)=O)c2ccccc12

InChI

1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m1/s1

InChI key

ZADWXFSZEAPBJS-SNVBAGLBSA-N

Application

Used to prepare a number of natural products including macroline alkaloids using the Pictet-Spengler reaction of tryptophan esters with aldehydes[1] also used in the synthesis of 1-substituted indolactam precursors.[2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Franco Carranza et al.
PloS one, 7(7), e40356-e40356 (2012-08-01)
Dendritic cells (DC) have the potential to control the outcome of autoimmunity by modulating the immune response. In this study, we tested the ability of Fasciola hepatica total extract (TE) to induce tolerogenic properties in CpG-ODN (CpG) maturated DC, to
Zhidan Tu et al.
Stem cells and development, 19(11), 1803-1809 (2010-02-19)
Mesenchymal stem cells (MSCs) possess potent and broad immunosuppressive capabilities, and have shown promise in clinical trials treating many inflammatory diseases. Previous studies have found that MSCs inhibit dendritic cell, T-cell, and B-cell activities in the adaptive immunity; however, whether
Longhao Sun et al.
Journal of personalized medicine, 12(12) (2022-12-24)
Pancreatic ductal adenocarcinoma (PDAC) represents one of the deadliest malignancies. Elevated regulatory T cell (Treg) infiltration has a potent immunosuppressive function in tumor biology, which contributes to low survival in PDAC. Nonetheless, the crosstalk between malignant cells and tumor-infiltrating Tregs
Dustin T Nguyen et al.
JCI insight (2022-11-25)
Autosomal dominant polycystic kidney disease (ADPKD), the most common monogenic nephropathy, is characterized by phenotypic variability exceeding genic effects. Dysregulated metabolism and immune cell function are key disease modifiers. The tryptophan metabolites, kynurenines, produced through IDO1, are known immunomodulators. Here
Cara C Schafer et al.
Oncotarget, 7(46), 75407-75424 (2016-10-06)
Indoleamine 2,3-dioxygenase (IDO) has been implicated in immune evasion by tumors. Upregulation of this tryptophan (Trp)-catabolizing enzyme, in tumor cells and myeloid-derived suppressor cells (MDSCs) within the tumor microenvironment (TME), leads to Trp depletion that impairs cytotoxic T cell responses

Questions

1–5 of 5 Questions  
  1. I have a question regarding 1-methyl-D-tryptophan (452483). Is this suitable for cell culture study purpose? Thank you.

    1 answer
    1. This product is listed as suitable for peptide synthesis. It may be okay for cell culture, but it is not tested with that application in mind, so the suitability would need to be determined by the end user. What is tested can be found on the product COA, an example of which can be found in the 'Documentation' section of the product page.

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  2. How should Product 452483, 1-Methyl-D-tryptophan, be stored?

    1 answer
    1. This material is stable at room temperature without any special handling precautions.

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  3. What is Product 452483, 1-Methyl-D-tryptophan, soluble in?

    1 answer
    1. While we don't test the solubility of this product directly, we do have to dissolve it in acetic acid in order to test the optical rotation. We would also expect this to be soluble in a dilute hydrochloric acid solution (50mg/mL in 5N HCl). Both heat and sonication may be required in order to prepare a homogenous solution. Also, based on our experience with the DL (Product No. 860646) and L (Product No. 447439) forms, we would expect that dilute sodium hydroxide would also be a potential solvent (1g/100mL of 1M NaOH).

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  4. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  5. What is the solution stability of Product 452483, 1-Methyl-D-tryptophan?

    1 answer
    1. Unfortunately, we do not perform solution stability testing on this item or have experience with storing tryptophan solutions, so we would recommend making a fresh batch with each use.

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