Acid-catalysed conversion of triethyleneimine thiophosphoramide (thio-TEPA) to an SH compound

Acid-catalysed conversion of triethyleneimine thiophosphoramide (thio-TEPA) to an SH compound

The behaviour of triethyleneimine thiophosphoramide (thio-TEPA) in acid medium has been studied. Evidence is presented of an intramolecular alkylation of the sulfur on protonation of the molecule. The five-membered ring formed in this way is hydrolyzed slowly in neutral solution at room temperature,...

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Veröffentlicht in:Biochemical pharmacology 1968, Vol.17 (1), p.55-64
1. Verfasser: Benckhuijsen, C.
Format: Artikel
Sprache:eng
Schlagworte:
Acids
Benzoates
Catalysis
Chromatography, Thin Layer
Cysteamine
Cysteine
Ethylenes
Ethylmaleimide
Hydrogen-Ion Concentration
Imines
Nitrobenzenes
Phenols
Pyridines
Sulfhydryl Compounds
Sulfur
Thiotepa
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Zusammenfassung:The behaviour of triethyleneimine thiophosphoramide (thio-TEPA) in acid medium has been studied. Evidence is presented of an intramolecular alkylation of the sulfur on protonation of the molecule. The five-membered ring formed in this way is hydrolyzed slowly in neutral solution at room temperature, liberating an SH group. In the SH derivative two ethyleneimine rings are retained, which were demonstrated to be more reactive towards water and sulfhydryl than were those of thio-TEPA.
ISSN:0006-2952
1873-2968
DOI:10.1016/0006-2952(68)90157-3