Total synthesis of nstx-3, spider toxin of nephila maculata

✍ Scribed by Tadashi Teshima; Takahiro Matsumoto; Tateaki Wakamiya; Tetsuo Shiba; Yoshio Aramaki; Terumi Nakajima; Nobufumi Kawai

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 544 KB
• Volume: 47
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86395-x

✦ Synopsis

A spider toxin NSTX-3 obtained from the venom of Papua New Guinean spider, Nephila muculata was synthesized in order to confirm its proposed structure and to supply the sample for the biological tests. The structure of NSTX-3 is now established as 2,4dihydroxyphenylacetyl-I,-Asn-tCadcPuatL-Arg, where Cad stands for cadaverine and Pua for putreanine. From the venom of a Papua New Guinean spider Nephila maculata, a new neurotoxin NSTX-3 was isolated which showed an irreversible suppression of the excitatory postsynaptic potential (RPSP) as well as the glutamate potential in the lobster neuromuscular junction. The structure of NSTX-3 was proposed as shown in Fig. lt), and established by our total synthesisz). The structure of JSTX3,l) a similar toxin obtained from the venom of Joro spider Nephilu cluvutu, was also proposed and confirmed by synthesis?)

After those synthetic studies, recently another synthesis of NSTX-3 as well as JSTX-3 were presented.4) Moreover, a variety of other spider toxins such as argiopin5). argiotoxina), and nephilatoxin7) were reported to have similar blocking action on the glutamate receptor. We wish to present now the details of our synthetic study of NSTX-3 which was undertaken to confirm the proposed structure and to supply the