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M0534

Sigma-Aldrich

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
Beilstein/REAXYS Number:
20225
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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DL-Tryptophan ≥99% (HPLC)

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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
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
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 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

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