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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%

Quality Level

100

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 also used in the synthesis of 1-substituted indolactam precursors.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7139
MKCR6694
MKCJ3953
MKCF0439
MKBZ1441V

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Irie, K. et al.
Tetrahedron, 51, 6255-6255 (1995)
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
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
Z Xie et al.
The British journal of dermatology, 177(3), 809-817 (2017-01-31)
The tryptophan-depleting enzyme indoleamine-2,3-dioxygenase (IDO) is critical for the regulation of immunotolerance and plays an important role in immune-associated skin diseases. To analyse the level of IDO in condyloma acuminata (CA) and its role in this condition. IDO expression was
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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