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Merck

T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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About This Item

经验公式(希尔记法):
C22H30N4O4
CAS号:
分子量:
414.50
MDL號碼:
分類程式碼代碼:
12352200
PubChem物質ID:
NACRES:
NA.56

生物源

fungus (Alternaria tenuis)

品質等級

化驗

≥95% (HPLC)

儲存溫度

2-8°C

SMILES 字串

CC(C)CC1NC(=O)C(C)N(C)C(=O)CNC(=O)\C(=C/c2ccccc2)N(C)C1=O

InChI

1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1

InChI 密鑰

SIIRBDOFKDACOK-LFXZBHHUSA-N

一般說明

Tentoxin is a majorly occurring cyclic tetrapeptide mycotoxin that is excreted by the Alternaria fungal species like Alternaria alternata and Alternaria tenuis.

生化/生理作用

It induces chlorosis in germinating seedlings of many dicotyledonous plants. Tentoxin has been postulated to inhibit cyclic photophosphorylation by acting as an energy transfer inhibitor at the terminal steps of ATP synthesis and to target the F1 moiety of photosynthetic H+-ATPases. A kinetic analysis of the action of tentoxin on the chloroplast F1 H+-ATPase (CF1) portion of chloroplast ATP synthase has been reported.
Tentoxin is phytotoxic, which induces chlorosis in plant leaves and germinating seedlings. It also halts photophosphorylation by inhibiting chloroplastic ATP synthase. Tentoxin over energizes thylakoids and is converted to isotentoxin by UV irradiation.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)


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Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
C Sigalat et al.
FEBS letters, 368(2), 253-256 (1995-07-17)
The effect of tentoxin at high concentrations was investigated in thylakoids and proteoliposomes containing bacteriorhodopsin and CF0CF1. Venturicidin-sensitive ATP hydrolysis, ATP-generated delta pH and ATP synthesis were practically 100% inhibited at 2 microM tentoxin, and restored to various extents beyond
Nicolas Loiseau et al.
Journal of peptide science : an official publication of the European Peptide Society, 8(7), 335-346 (2002-08-01)
Tentoxin is a naturally occurring phytotoxic cyclic tetrapeptide excreted by fungi of the Alternaria alternata family. The four total syntheses of tentoxin published to date give poor total yields, mainly owing to two difficulties, the introduction of the dehydro amino
Georg Groth
Proceedings of the National Academy of Sciences of the United States of America, 99(6), 3464-3468 (2002-03-21)
Tentoxin, a natural cyclic tetrapeptide produced by phytopathogenic fungi from the Alternaria species affects the catalytic function of the chloroplast F(1)-ATPase in certain sensitive species of plants. In this study, we show that the uncompetitive inhibitor tentoxin binds to the
Georg Groth et al.
The Journal of biological chemistry, 277(23), 20117-20119 (2002-04-12)
In contrast to the homologous bacterial and mitochondrial enzymes the chloroplast F(1)-ATPase (CF(1)) is strongly affected by the phytopathogenic inhibitor tentoxin. Based on structural information obtained from crystals of a CF(1)-tentoxin co-complex (Groth, G. (2002) Proc. Natl. Acad. Sci. U.

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