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Key Documents

M0534

Sigma-Aldrich

5-Methyl-DL-tryptophan

tryptophan analog

Sinônimo(s):

5-Methyltryptophan

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About This Item

Fórmula empírica (Notação de Hill):
C12H14N2O2
Número CAS:
Peso molecular:
218.25
Beilstein:
20225
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de substância PubChem:
NACRES:
NA.26

Nível de qualidade

Ensaio

≥97% (TLC)

forma

powder

cor

white to faint yellow

pf

280-282 °C

aplicação(ões)

peptide synthesis

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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)

chave InChI

HUNCSWANZMJLPM-UHFFFAOYSA-N

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Aplicação


  • 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).

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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DL-Tryptophan ≥99% (HPLC)

Sigma-Aldrich

162698

DL-Tryptophan

D-Tryptophan ≥98.0% (HPLC)

Sigma-Aldrich

T9753

D-Tryptophan

L-Tryptophan from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%

Sigma-Aldrich

T8941

L-Tryptophan

L-Tryptophan reagent grade, ≥98% (HPLC)

Sigma-Aldrich

T0254

L-Tryptophan

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
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
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
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
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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