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447439

Sigma-Aldrich

1-Methyl-L-tryptophan

95%, for peptide synthesis

Synonym(e):

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

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CHF 52.30
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CHF 159.00

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Voraussichtliches Versanddatum14. April 2025


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1 G
CHF 52.30
5 G
CHF 159.00

About This Item

Empirische Formel (Hill-System):
C12H14N2O2
CAS-Nummer:
Molekulargewicht:
218.25
MDL-Nummer:
UNSPSC-Code:
12352209
PubChem Substanz-ID:
NACRES:
NA.22

CHF 52.30


Voraussichtliches Versanddatum14. April 2025


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Produktbezeichnung

1-Methyl-L-tryptophan, 95%

Qualitätsniveau

Assay

95%

Form

solid

Optische Aktivität

[α]24/D −8.0°, c = 2 in acetic acid

Eignung der Reaktion

reaction type: solution phase peptide synthesis

mp (Schmelzpunkt)

242-245 °C (lit.)

Anwendung(en)

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

InChIKey

ZADWXFSZEAPBJS-JTQLQIEISA-N

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Anwendung

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.[1]
  • As a key starting material for the total synthesis of (−)-ardeemin.[2]
  • In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.[3]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Kunden haben sich ebenfalls angesehen

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
Cyclic peptide-capped gold nanoparticles as drug delivery systems.
Nasrolahi Shirazi A, et al.
Molecular Pharmaceutics, 10(2), 500-511 (2012)
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)
Christiane A Opitz et al.
PloS one, 6(5), e19823-e19823 (2011-06-01)
1-methyl-D-tryptophan (1-D-MT) is currently being used in clinical trials in patients with relapsed or refractory solid tumors with the aim of inhibiting indoleamine-2,3-dioxygenase (IDO)-mediated tumor immune escape. IDO is expressed in tumors and tumor-draining lymph nodes and degrades tryptophan (trp)
Jeroen F J Bogie et al.
Journal of neuroinflammation, 8, 85-85 (2011-07-26)
Multiple sclerosis (MS) is a chronic, inflammatory, demyelinating disease of the central nervous system (CNS) in which macrophages play a central role. Initially, macrophages where thought to be merely detrimental in MS, however, recent evidence suggests that their functional phenotype

Questions

1–4 of 4 Questions  
  1. What conditions do you recommend for long term storage of Product No. 447439, 1-Methyl-L-tryptophan?

    1 answer
    1. The long term storage temperature of the product 447139 is at room temperature. This information can be found in the MSDS sheet. This document is available from our website.

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  2. The name of Product No. 447439 is "1-Methyl-L-tryptophan, 95%". How is that purity value determined?

    1 answer
    1. The purity of Product No. 447439 is based on elemental analysis. That is, the assayed values for percent carbon and nitrogen should be within about 95% of their theoretical values. But the speification sheet does not report an overall purity value per se.

      Helpful?

  3. How do you recommend dissolving Product No. 447439, 1-Methyl-L-tryptophan?

    1 answer
    1. This product is soluble in 0.5 N Hydrochloric acid at 50 mg/mL. Based on information from one of our customers (not confirmed in our labs), this product is also soluble in 0.1 N sodium hydroxide at a 20 mM concentration. It is not soluble in DMSO.

      Helpful?

  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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