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447439

1-Methyl-L-tryptophan

Name: 1-Methyl-<SC>L</SC>-tryptophan
Brand: ALDRICH

95%, for peptide synthesis

Synonym(s):

(S)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid, L-(-)-1-Methyltryptophan

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄N₂O₂

CAS Number:

21339-55-9

Molecular Weight:

218.25

UNSPSC Code:

12352209

PubChem Substance ID:

24868339

NACRES:

NA.22

MDL number:

MFCD00467133

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Properties

Product Name

1-Methyl-L-tryptophan, 95%

Quality Level

100

assay

95%

form

solid

optical activity

[α]24/D −8.0°, 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-/m0/s1

InChI key

ZADWXFSZEAPBJS-JTQLQIEISA-N

Description

Application

1-Methyl-L-tryptophan can be used:

In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N²-arylation of 1,2,3-triazoles.
As a key starting material for the total synthesis of (−)-ardeemin.
In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Fibroblastic reticular cells from lymph nodes attenuate T cell expansion by producing nitric oxide.

Stefanie Siegert et al.

PloS one, 6(11), e27618-e27618 (2011-11-24)

Adaptive immune responses are initiated when T cells encounter antigen on dendritic cells (DC) in T zones of secondary lymphoid organs. T zones contain a 3-dimensional scaffold of fibroblastic reticular cells (FRC) but currently it is unclear how FRC influence

Development of a L?Tryptophan?Based Ligand for Regioselective Copper Catalyzed N2?Arylation of 1, 2, 3?Triazoles.

Lopes A B, et al.

ChemistrySelect, 2(22), 6544-6548 (2017)

Inhibition of Indoleamine-2,3-dioxygenase (IDO) in Glioblastoma Cells by Oncolytic Herpes Simplex Virus.

Bonnie Reinhart et al.

Advances in virology, 2012, 815465-815465 (2012-08-28)

Successful oncolytic virus treatment of malignant glioblastoma multiforme depends on widespread tumor-specific lytic virus replication and escape from mitigating innate immune responses to infection. Here we characterize a new HSV vector, JD0G, that is deleted for ICP0 and the joint

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Global Trade Item Number

SKU	GTIN
447439-5G	04061832288581
447439-1G	04061832288574