5-Methyl-DL-tryptophan

SIGMA/M0534 - tryptophan analog

Synonym: 5-Methyltryptophan

CAS Number: 951-55-3
Empirical Formula (Hill Notation): C₁₂H₁₄N₂O₂
Molecular Weight: 218.25
EC Number: 213-453-6
MDL Number: MFCD00005652
Linear Formula: C₁₂H₁₄N₂O₂
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-M0534-250MG	250 mg	$291.00 1/EA	Add To Favorites
45-M0534-1G	1 g	$580.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: M0534-1G

Properties
Descriptions
Safety Info.
Basic Data

application(s)	peptide synthesis
assay	≥97% (TLC)
color	white to faint yellow
form	powder
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
mp	280-282 °C
Quality Level	200
SMILES string	Cc1ccc2[nH]cc(CC(N)C(O)=O)c2c1
storage temp.	2-8°C

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. 5-Methyl-DL-tryptophan is a corepressor of the E. coli trp repressor.
Biochem/physiol Actions:	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.
Packaging:	1 g in glass bottle
Packaging:	250 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥97% (TLC)
mp	280-282 °C
Storage Temp.	2-8°C
UNSPSC	12352209

To Order From a Quote