M0534

5-Methyl-DL-Tryptophan

tryptophan analog

• Synonym(e): 5-Methyltryptophan
• Empirische Formel (Hill-System): C₁₂H₁₄N₂O₂
• CAS-Nummer: 951-55-3
• Molekulargewicht: 218.25
• Beilstein: 20225
• EG-Nummer: 213-453-6
• MDL-Nummer: MFCD00005652
• UNSPSC-Code: 12352209
• PubChem Substanz-ID: 24896560
• NACRES: NA.26

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥97% (TLC)
• Form: powder
• Farbe: white to faint yellow
• mp (Schmelzpunkt): 280-282 °C
• Anwendung(en): peptide synthesis
• Lagertemp.: 2-8°C
• SMILES String: Cc1ccc2[nH]cc(CC(N)C(O)=O)c2c1
• InChI: 1S/C12H14N2O2/c1-7-2-3-11-9(4-7)8(6-14-11)5-10(13)12(15)16/h2-4,6,10,14H,5,13H2,1H3,(H,15,16)
• InChIKey: HUNCSWANZMJLPM-UHFFFAOYSA-N

Beschreibung

Anwendung

• Amelioration of colitis through modulation of gut microbiota: The metabolite 5-Methyl-ᴅʟ-tryptophan (5-MT), derived from Angelica sinensis polysaccharides, was found to ameliorate colitis by modulating gut microbiota and the TLR4/MyD88/NF-κB signaling pathway. This suggests a potential application of 5-MT in inflammatory bowel disease research and therapy (Zou et al., 2023).


• Enzymatic synthesis of tryptophan derivatives: A study on the one-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids highlights a method using a turnip enzyme. This research outlines a novel approach to synthesizing tryptophan derivatives, potentially useful in biochemical assays (Ryu et al., 2021).

Biochem./physiol. Wirkung

5-Methyl-DL-tryptophan inhibits the synthesis of anthranilate compounds that are the first steps in the biosynthesis of tryptophan in Neurospora crassa. 5-Methyl-DL-tryptophan is a corepressor of the E. coli trp repressor.

5-Methyl-DL-tryptophan may be used to select genetic mutants of PS strain of Methanococcus voltae (archaebacteria). 5-Methyl-tryptophan is a repressor trp operon expression. 5-Methyl-tryptophan is a substrate for tryptophanase. 5-Methyl-tryptophan inhibits the induction of anthranilate synthase activity by elicitors in oats.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)