Tetrahedron p. 4503 - 4510 (1986)
Update date:2022-07-30
Topics:
Plate, Ralf
Nivard, Rutger J. F.
Ottenheijm, Harry C. J.
The 3-S-(cysteinyl)indoles 8a and 8b, easily derived (ca 95percent yield) from indole and the sulfenyl chlorides 7a and 7b, respectively, have been converted (ca 50percent) into oximino derivatives of tryptophan 9a,b.Reduction gave a mixture of two diastereomeric 2-S-(cysteinyl)tryptophan derivatives - i.e. 10 and its H2N-C(α)epimer - which could be separated.One of these is a derivative of tryptathionine, the characterictic structural element of toxic principles (e.g.Phalloin (5)) of members of the genus Amanita.
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