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T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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250 μG
238,00 €
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712,00 €

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Cambia visualizzazione
250 μG
238,00 €
1 MG
712,00 €

About This Item

Formula empirica (notazione di Hill):
C22H30N4O4
Numero CAS:
28540-82-1
Peso molecolare:
414.50
Numero MDL:
MFCD00133844
Codice UNSPSC:
12352200
ID PubChem:
24900492
NACRES:
NA.56

238,00 €

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Origine biologica

fungus (Alternaria tenuis)

Livello qualitativo

200

Saggio

≥95% (HPLC)

Temperatura di conservazione

2-8°C

Stringa SMILE

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
SIIRBDOFKDACOK-LFXZBHHUSA-N

Descrizione generale

Tentoxin is a majorly occurring cyclic tetrapeptide mycotoxin that is excreted by the Alternaria fungal species like Alternaria alternata and Alternaria tenuis.[1]

Azioni biochim/fisiol

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.[2] It also halts photophosphorylation[1] by inhibiting chloroplastic ATP synthase.[2] Tentoxin over energizes thylakoids and is converted to isotentoxin by UV irradiation.[3]

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
0000165435
0000165434
089M4098V
14160612
058M4115V

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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
Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
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.
Nicolas Loiseau et al.
Biopolymers, 69(3), 363-385 (2003-07-02)
Biologically active cyclic tetrapeptides, usually found among fungi metabolites, exhibit phytotoxic or cytostatic activities that are likely to be governed by specific conformations adopted in solution. For conformational studies and drug design, there is a strong interest in using fast
Jose C Jiménez et al.
Organic letters, 5(12), 2115-2118 (2003-06-07)
[reaction: see text] A solid-phase method for the synthesis of tentoxin has been developed. Two key steps-dehydration and N-alkylation-are carried out while the peptide is anchored to the resin. The method, which has been validated by the preparation of a
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