ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Optimization of the Synthesis of 2-Indole Thioethers from Derivatives of Tryptophan ond CysteineThe coupling reaction between cysteine-sulfur and the 2-position of the indole nucleus of tryptophan that yields tryptathionine (4), the chromophoric system fo the phallotoxines, has been made reproducible and profitable by using glacial acetic acid as solvent. The formation of the intermediate S-chloride from cysteine derivative and N-chlorosuccinimide at room temperature is followed colorimetrically, and the tryptophan derivative is added at the moment of maximum extinction (table 1).
Notes:
Die Verknüpfung des Cystein-Schwefels mit der 2-Stellung des Tryptophan-indols zum Thioäther Tryptathionin (4), dem Chromophor der Phallotoxine, wird zu einer reproduzierbaren, ertragreichen Reaktion, wenn man ohne äußere Kühlung die Bildung des S-Chlorids aus dem Cystein-Derivat mit N-Chlor-succinimid in Eisessig unter kolorimetrischer Kontrolle vornimmt und zum Zeitpunkt der maximalen Extinktion das Tryptophan-Derivat zusetzt (Tab. 1).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.19697270117
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