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M0534

5-Methyl-DL-Tryptophan

Name: 5-Methyl-<SC>DL</SC>-Tryptophan
Brand: SIGMA

tryptophan analog

Synonym(e):

5-Methyltryptophan

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About This Item

Empirische Formel (Hill-System):

C₁₂H₁₄N₂O₂

CAS-Nummer:

951-55-3

Molekulargewicht:

218.25

Beilstein:

20225

EG-Nummer:

213-453-6

MDL-Nummer:

MFCD00005652

UNSPSC-Code:

12352209

PubChem Substanz-ID:

24896560

NACRES:

NA.26

Qualitätsniveau

200

Assay

≥97% (TLC)

Form

powder

Farbe

white to faint yellow

mp (Schmelzpunkt)

280-282 °C

Anwendung(en)

peptide synthesis

Lagertemp.

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)

InChIKey

HUNCSWANZMJLPM-UHFFFAOYSA-N

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Anwendung

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. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

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Targeting a nuclear anthranilate synthase alpha-subunit gene to the tobacco plastid genome results in enhanced tryptophan biosynthesis. Return of a gene to its pre-endosymbiotic origin.

X H Zhang et al.

Plant physiology, 127(1), 131-141 (2001-09-13)

Anthranilate synthase (AS), the control enzyme of the tryptophan (Trp) biosynthetic pathway, is encoded by nuclear genes, but is transported into the plastids. A tobacco (Nicotiana tabacum) cDNA (ASA2) encoding a feedback-insensitive tobacco AS alpha-subunit was transformed into two different

In vivo regulation of intermediate reactions in the pathway of tryptophan biosynthesis in Neurospora crassa.

G Lester

Journal of bacteriology, 96(5), 1768-1773 (1968-11-01)

The in vivo regulation of intermediate reactions in the pathway of tryptophan synthesis in Neurospora crassa was examined in a double mutant (tr-2, tr-3) which lacks the functions of the first and last enzymes in the pathway from chorismic acid

Expression of a bacterial feedback-insensitive 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase of the shikimate pathway in Arabidopsis elucidates potential metabolic bottlenecks between primary and secondary metabolism.

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

Induction of anthranilate synthase activity by elicitors in oats.

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

NMR studies of the activation of the Escherichia coli trp repressor.

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

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