M0534
5-Methyl-DL-tryptophan
tryptophan analog
Synonym(s):
5-Methyltryptophan
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About This Item
Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
Molecular Weight:
218.25
UNSPSC Code:
12352209
NACRES:
NA.26
PubChem Substance ID:
EC Number:
213-453-6
Beilstein/REAXYS Number:
20225
MDL number:
InChI key
HUNCSWANZMJLPM-UHFFFAOYSA-N
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)
SMILES string
Cc1ccc2[nH]cc(CC(N)C(O)=O)c2c1
assay
≥97% (TLC)
form
powder
color
white to faint yellow
mp
280-282 °C
application(s)
peptide synthesis
storage temp.
2-8°C
Quality Level
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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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Tetsuya Matsukawa et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 57(1-2), 121-128 (2002-04-03)
Oat phytoalexins, avenanthramides, are a series of substituted hydroxycinnamic acid amides with anthranilate. The anthranilate in avenanthramides is biosynthesized by anthranilate synthase (AS, EC 4.1.3.27). Induction of anthranilate synthase activity was investigated in oat leaves treated with oligo-N-acetylchitooligosaccharide elicitors. AS
Vered Tzin et al.
The New phytologist, 194(2), 430-439 (2012-02-03)
The shikimate pathway of plants mediates the conversion of primary carbon metabolites via chorismate into the three aromatic amino acids and to numerous secondary metabolites derived from them. However, the regulation of the shikimate pathway is still far from being
E I Hyde et al.
European journal of biochemistry, 201(3), 569-579 (1991-11-01)
The Escherichia coli trp repressor binds to the trp operator in the presence of tryptophan, thereby inhibiting tryptophan biosynthesis. Tryptophan analogues lacking the alpha-amino group act as inducers of trp operon expression. We have used one- and two-dimensional 1H-NMR spectroscopy
Paoyuan Hsiao et al.
Planta, 225(4), 897-906 (2006-10-14)
Gene transformation is an integral tool for plant genetic engineering. All antibiotic resistant genes currently employed are of bacterial origin and their presence in the field is undesirable. Therefore, we developed a novel and efficient plant native non-antibiotic selection system
H J Cho et al.
Plant physiology, 123(3), 1069-1076 (2000-07-13)
A cDNA clone that encodes a feedback-insensitive anthranilate synthase (AS), ASA2, isolated from a 5-methyl-tryptophan (Trp) (5MT)-resistant tobacco cell line under the control of the constitutive cauliflower mosaic virus 35S promoter, was introduced into the forage legume Astragalus sinicus by
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