Abstract
Tentoxin 1 (TTX)1 is a natural cyclic tetrapeptide (cyclo(L-NMeAla-L-LeuNMeiΔ(Z)Phe-Gly)) produced by the phytopathogenic fungus Alternaria alternata. This cyclopeptide is a selective weedkiller which causes the chlorosis of some higher plants2. A possible mechanism involves the inhibition of photophosphorylation in the chloroplasts. In vitro and at low concentrations (10-8-10-7), TTX inhibits the F1 moiety of H+ATPsynthase, but at higher concentrations it stimulates the ATPase activity3. 4. TTX is the only natural effector known to inhibit the catalytic part of chloroplast ATP-synthase, and is noncompetitive for nucleotide binding. In order to understand this mechanism we developed a large number of TTX analogues, either by total synthesis and chemical modification, or by biotransformation. This report describes the study of two close analogues: dihydro-tentoxin (DH-TTX)2 a metabolite also isolated from Alternaria alternata and presumably precursor of TTX during its biosynthesis, and iso-tentoxin (Iso-TTX)3 a photochemical derivative of TTX.
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Loiseau, N. et al. (2001). Structure-Activity Relationships of Cyclotetrapeptides: Interaction of Tentoxin Derivatives with Three Membrane Proteins. In: Dansette, P.M., et al. Biological Reactive Intermediates VI. Advances in Experimental Medicine and Biology, vol 500. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-0667-6_55
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DOI: https://doi.org/10.1007/978-1-4615-0667-6_55
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