M0534

5-Methyl-DL-tryptophan

tryptophan analog

• Synonym(s): 5-Methyltryptophan
• Empirical Formula (Hill Notation): C₁₂H₁₄N₂O₂
• CAS Number: 951-55-3
• Molecular Weight: 218.25
• UNSPSC Code: 12352209
• NACRES: NA.26
• PubChem Substance ID: 24896560
• EC Number: 213-453-6
• Beilstein/REAXYS Number: 20225
• MDL number: MFCD00005652

Properties

• Quality Segment: 200
• assay: ≥97% (HPLC)
• form: powder
• color: white to faint yellow
• mp: 280-282 °C
• application(s): peptide synthesis
• storage temp.: 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)
• InChI key: HUNCSWANZMJLPM-UHFFFAOYSA-N

Description

Application

• 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 Actions

5-Methyl-DL-tryptophan inhibits the synthesis of anthranilate compounds that are the first steps in the biosynthesis of tryptophan in Neurospora crassa.[1] 5-Methyl-DL-tryptophan is a corepressor of the E. coli trp repressor.[2][3]

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)