M0534
5-Methyl-DL-tryptophan
tryptophan analog
Synonym(s):
5-Methyltryptophan
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
Molecular Weight:
218.25
Beilstein:
20225
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
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Quality Level
Assay
≥97% (TLC)
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
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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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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
Y Tozawa et al.
Plant physiology, 126(4), 1493-1506 (2001-08-14)
Anthranilate synthase (AS) is a key enzyme in the synthesis of tryptophan (Trp), indole-3-acetic acid, and indole alkaloids. Two genes, OASA1 and OASA2, encoding AS alpha-subunits were isolated from a monocotyledonous plant, rice (Oryza sativa cv Nipponbare), and were characterized.
H Kisaka et al.
Plant molecular biology, 38(5), 875-878 (1998-12-23)
A cDNA clone encoding rice tryptophan synthase beta (TSB) was isolated and its transcript level was examined in TR-No. 73, a derivative of a previously isolated rice mutant (TR-1) that is resistant to 5-methyltryptophan. The cDNA sequence of the rice
G Bertani et al.
Journal of bacteriology, 169(6), 2730-2738 (1987-06-01)
Mutations causing requirements for histidine, purine, and vitamin B12 were obtained in strain PS of Methanococcus voltae (archaebacteria) upon irradiation with UV or gamma rays. The first two mutations were shown to revert at low frequencies and were used to
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