M0534
5-甲基- DL -色氨酸
tryptophan analog
别名:
5-Methyltryptophan
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关于此项目
经验公式（希尔记法）:
C12H14N2O2
化学文摘社编号:
分子量:
218.25
UNSPSC Code:
12352209
NACRES:
NA.26
PubChem Substance ID:
EC Number:
213-453-6
Beilstein/REAXYS Number:
20225
MDL number:
产品名称
5-甲基- DL -色氨酸, tryptophan analog
InChI key
HUNCSWANZMJLPM-UHFFFAOYSA-N
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)
SMILES string
Cc1ccc2[nH]cc(CC(N)C(O)=O)c2c1
assay
≥97% (TLC)
form
powder
color
white to faint yellow
mp
280-282 °C
application(s)
peptide synthesis
storage temp.
2-8°C
Quality Level
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Application
- 通过调节肠道菌群缓解结肠炎：代谢产物5-甲基-ʟ-色氨酸(5-MT)来自当归多糖，可通过调节肠道菌群和TLR4/MyD88/NF-κB信号通路缓解结肠炎。说明5-MT在炎症性肠病研究和治疗中的应用前景(Zou et al., 2023)。
- 色氨酸衍生物的酶促合成：研究由氨基酸通过一锅对映选择性合成天然(S)-spirobrassinin和非天然(S)-甲基spirobrassinin，使用芜菁酶。介绍一种色氨酸衍生物的新合成方法，适合用于生化分析(Ryu et al., 2021)。
Biochem/physiol Actions
5-甲基- DL -色氨酸抑制邻氨基苯甲酸酯化合物的合成，该化合物是粗糙脉孢菌 色氨酸生物合成的第一步 。5-甲基- DL -色氨酸是大肠杆菌色氨酸阻抑物的辅阻遏子。
5-甲基-DL-色氨酸可用于选择 产甲烷菌 （原始细菌）PS 株的基因突变株。5-甲基色氨酸是一种抑制色氨酸操纵子表达。5-甲基色氨酸是色氨酸酶的底物。5-甲基色氨酸抑制燕麦中激发子对邻氨基苯甲酸合成酶活性的诱导。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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
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 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
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