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Principaux documents

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M0534

Sigma-Aldrich

5-Methyl-DL-tryptophan

tryptophan analog

Synonyme(s) :

5-Methyltryptophan

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About This Item

Formule empirique (notation de Hill):
C12H14N2O2
Numéro CAS:
951-55-3
Poids moléculaire :
218.25
Beilstein:
20225
Numéro CE :
213-453-6
Numéro MDL:
MFCD00005652
Code UNSPSC :
12352209
ID de substance PubChem :
24896560
Nomenclature NACRES :
NA.26

Niveau de qualité

200

Essai

≥97% (TLC)

Forme

powder

Couleur

white to faint yellow

Pf

280-282 °C

Application(s)

peptide synthesis

Température de stockage

2-8°C

Chaîne 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)

Clé InChI

HUNCSWANZMJLPM-UHFFFAOYSA-N

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Catégories apparentées

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).

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000406790
0000406790
0000371476
0000371477
0000351527

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5-Hydroxy-L-tryptophan 98% (calc. on dried substance)

Sigma-Aldrich

107751

5-Hydroxy-L-tryptophan

DL-Tryptophan ≥99% (HPLC)

Sigma-Aldrich

162698

DL-Tryptophan

D-Tryptophan ≥98.0% (HPLC)

Sigma-Aldrich

T9753

D-Tryptophan

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

Sigma-Aldrich

T8941

L-Tryptophane

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

Sigma-Aldrich

T0254

L-Tryptophane

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 Zhao et al.
Science (New York, N.Y.), 291(5502), 306-309 (2001-02-24)
Although auxin is known to regulate many processes in plant development and has been studied for over a century, the mechanisms whereby plants produce it have remained elusive. Here we report the characterization of a dominant Arabidopsis mutant, yucca, which
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.
Mohamed El Khattabi et al.
The Biochemical journal, 409(1), 193-198 (2007-10-04)
Incorporation of Trp (tryptophan) analogues into a protein may facilitate its structural analysis by spectroscopic techniques. Development of a biological system for the biosynthetic incorpor-ation of such analogues into proteins is of considerable importance. The Gram-negative Escherichia coli is the
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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