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447439

Sigma-Aldrich

1-Methyl-L-tryptophan

95%, for peptide synthesis

Synonyme(s) :

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

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68,20 €
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138,00 €

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1 G
68,20 €
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About This Item

Formule empirique (notation de Hill) :
C12H14N2O2
Numéro CAS:
21339-55-9
Poids moléculaire :
218.25
Numéro MDL:
MFCD00467133
Code UNSPSC :
12352209
ID de substance PubChem :
24868339
Nomenclature NACRES :
NA.22

68,20 €

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Devis pour commande en gros

Nom du produit

1-Methyl-L-tryptophan, 95%

Niveau de qualité

100

Essai

95%

Forme

solid

Activité optique

[α]24/D −8.0°, c = 2 in acetic acid

Capacité de réaction

reaction type: solution phase peptide synthesis

Pf

242-245 °C (lit.)

Application(s)

peptide synthesis

Chaîne SMILES 

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

Clé InChI

ZADWXFSZEAPBJS-JTQLQIEISA-N

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Catégories apparentées

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.[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]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
MKCQ0187
MKCJ1127
MKCC7257
MKCC3400
MKBZ4985V

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L-Tryptophane reagent grade, ≥98% (HPLC)

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K3375

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α-(Methylamino)isobutyric acid ≥97% (titration)

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M2383

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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)
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
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)
Total synthesis of (?)-ardeemin.
He B, et al.
The Journal of Organic Chemistry, 74(1), 298-304 (2008)
Cyclic peptide-capped gold nanoparticles as drug delivery systems.
Nasrolahi Shirazi A, et al.
Molecular Pharmaceutics, 10(2), 500-511 (2012)
Afficher tous les articles scientifiques apparentés

Questions

1–6 of 6 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. 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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  4. 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.

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  5. 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.

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  6. 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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