l-Canavanine: a higher plant insecticidal allelochemical

@article{Rosenthal2001lCanavanineAH,
  title={l-Canavanine: a higher plant insecticidal allelochemical},
  author={G. Rosenthal},
  journal={Amino Acids},
  year={2001},
  volume={21},
  pages={319-330}
}
Summary.l-Canavanine, l-2-amino-4-(guanidinooxy)butyric acid, is a potentially toxic nonprotein amino acid of certain leguminous plants. Many species are prolific canavanine producers; they divert enormous nitrogen resource to the storage of this single natural product. Canavanine, a highly effective protective allelochemical, provides a formidable chemical barrier to predation and disease.The accumulated experimental evidence leaves little doubt that the key element in the ability of… Expand
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L-Canavanine, a nonprotein amino acid of certain leguminous plants, manifests potent insecticidal properties in a canavanine-sensitive insect such as the tobacco hornworm Manduca sexta (L.)Expand
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The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability, and it was revealed that these esters are less toxic thanCanavanine ; the ethyl ester disrupted larval growth more than did the methyl analogue. Expand
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Feeding studies revealed H. virescens to be resistant to the potentially insecticidal effects of this allelochemical in larval stages and could not cope with all potentially toxic nonprotein amino acids. Expand
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TLDR
Experimental evidence is presented that the innocuous nature of homoarginine results from the elevated pKa value of its guanidino group which arguably exceeds even that of arginine, and as a result, homo arginine does not disrupt essential residue interactions. Expand
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TLDR
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