A new class of sulfoxide surfactants derived from Tris. Synthesis and preliminary assessments of their properties

A new class of non-ionic amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins, is reported. Such surfactants were prepared in two steps : addition of alkyl or fluoroalkyl mercaptan on Tris(hydroxymethyl)acrylamidomethane (THAM) derivatives, followed by t...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 1998-06, Vol.8 (12), p.1559-1562
Hauptverfasser: Barthélémy, Philippe, Maurizis, Jean Claude, Lacombe, Jean Michel, Pucci, Bernard
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container_issue 12
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container_title Bioorganic & medicinal chemistry letters
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creator Barthélémy, Philippe
Maurizis, Jean Claude
Lacombe, Jean Michel
Pucci, Bernard
description A new class of non-ionic amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins, is reported. Such surfactants were prepared in two steps : addition of alkyl or fluoroalkyl mercaptan on Tris(hydroxymethyl)acrylamidomethane (THAM) derivatives, followed by the oxydation of sulfide group in sulfoxide moiety in order to provide water solubility to the molecule. The detergent efficiency of these new surfactants were assayed on rat liver cells. Ionic or free radical addition of alkyl or fluoroalkyl mercaptan (RSH) on Tris(hydroxymethyl)acrylamidomethane, then oxydation of sulfide in sulfoxide moiety lead to new non ionic surfactants which could be used for protein solubilization.
doi_str_mv 10.1016/S0960-894X(98)00263-7
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source MEDLINE; Access via ScienceDirect (Elsevier)
subjects Animals
Biological and medical sciences
Biotechnology
Cell Nucleus - drug effects
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Microsomes, Liver - drug effects
Mitochondria, Liver - drug effects
non-ionic surfactant
Others
perfluoroalkyl surfactant
protein extraction
Rats
sulfoxide
Sulfoxides - chemical synthesis
Sulfoxides - chemistry
Sulfoxides - pharmacology
Surface-Active Agents - chemical synthesis
Surface-Active Agents - chemistry
Surface-Active Agents - pharmacology
Tris
Tromethamine - chemistry
Various methods and equipments
title A new class of sulfoxide surfactants derived from Tris. Synthesis and preliminary assessments of their properties
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