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Formation of Potentially Prebiotic Amphiphiles by Reaction of β‐Hydroxy‐ n ‐alkylamines with Cyclotriphosphate
Author(s) -
Mullen Lee B.,
Sutherland John D.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200700394
Subject(s) - prebiotic , amphiphile , pulmonary surfactant , chemistry , reactivity (psychology) , phosphate , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry , copolymer , medicine , alternative medicine , pathology , polymer
The long and the short of it : In water, long‐chain β‐hydroxy‐ n ‐alkylamines are converted to their O ‐monophosphates by reaction with cyclotriphosphate. With short‐chain β‐hydroxy‐ n ‐alkylamines, N ‐triphosphates are formed instead. The difference results from the formation of surfactant assemblies from the long‐chain compounds. This surfactant control of reactivity may be of relevance to the prebiotic formation of amphiphiles. (P): phosphate unit.