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Synthetic Analogues to the Spermidine‐Spermine Alkaloid Tenuilobine
Author(s) -
Popaj Kasim,
Guggisberg Armin,
Hesse Manfred
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001108)83:11<3021::aid-hlca3021>3.0.co;2-e
Subject(s) - chemistry , spermidine , spermine , polyamine , moiety , spider toxin , stereochemistry , alkaloid , biochemistry , peptide , amino acid , receptor , glutamate receptor , enzyme
Naturally occurring spider and wasp toxins are potent inhibitors of glutamate receptors in the central nervous system. They consist of a polyamine backbone and carboxylic acids or amino acids linked by peptide bonds. In some respects, the plant alkaloid tenuilobine, a derivative of spermine and spermidine, shows structural similarities to these toxins. In the present paper, the synthesis of the five tenuilobine analogs 12 , 13 , 15 , 24 , and 25 is described. These derivatives differ in their aromatic carboxylic acid subunits and in the polyamine moiety.