Amino Acids 2003-04-01

Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins.

T Shinada, Y Nakagawa, K Hayashi, G Corzo, T Nakajima, Y Ohfune

Index: Amino Acids 24(3) , 293-301, (2003)

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Abstract

Eight analogs 4A-7A and 4B-7B of philanthotoxin (PhTX) from wasp venom and nephilatoxin-8 (NPTX-8) from spider venom whose tyrosine or asparagine linker is replaced by squaryl (sq) amino acid or 4-amino squaryl (4-asq) amino acid have been synthesized in an efficient manner via coupling of N-acyl squaryl amino acid intermediate 19 or 26 with the corresponding polyamine part. Preliminary bioassay using crickets revealed that the analogs substituted by glutamate-type squaryl amino acid-containing NPTX 7A and 7B showed more potent paralytic activities than that of NPTX-8.


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