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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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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
110117-83-4
Molecular Weight:
218.25
MDL number:
MFCD00274271
UNSPSC Code:
12352209
PubChem Substance ID:
24868706
NACRES:
NA.22

product name

1-Methyl-D-tryptophan, 95%

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

Related Categories

Application

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

452483-250MG:
452483-VAR:
452483-BULK:
452483-1G:
452483-10G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Irie, K. et al.
Tetrahedron, 51, 6255-6255 (1995)
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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
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
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
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