Telomers of Tris(hydroxymethyl)-acrylamidomethane, a new class of non-ionic surfactants: Synthesis and assessment of their properties

Article abstract of DOI:10.1016/0040-4039(91)80351-6

A new class of amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins and/or glycoproteins, is reported. These compounds were prepared by telomerization of a Tris-(hydroxymethyl)-acrylamidomethane monomeric unit in the presence of an alkyl thiol as transfer reagent and of α,α'-(azobis)-isobutyronitrile (AIBN) as initiator. These compounds show similar or better detergent properties than commercially available surfactants.

Full text of DOI:10.1016/0040-4039(91)80351-6

Tet,~hcdton Letters, Vul.32, No,l 1, pp 1437 1440. 1991
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TELOMERS OF TRIS(IIYDROXYMETHYL)-ACRYLAMIDOMETHANE,
A NEW CLASS OF NON-IONIC
SURFACTANTS : SYNTIIESIS AND ASSESSMENT OF THEIR PROPERTIES.
BernardPucel and Andre A. Pavia*
Laboratoirc de Chimie Bioorganique, Faeult~ des Sciences d'Avignon,
33, rue Louis Pasteur, 84000 Avignon, France.
Abstract :
A new class of amphiphilic molecules suitable for biological purposes, especially extraction of
membrane proteins and/or glycoproteins, is reported These compounds were prepared by telomerization of a
Tris-(hydroxymethyl) acrylamidomethane monomeric unit in the presence of an alkyl thiol as transfer reagent
and of t~,tz' (azobis)-isobutyronittile (AIBN) as initiator. These compounds show similar or better detergent
properties than commercially available surtactants.
The study of the various intramembraneous cell compoaents, especially proteins and/t~r glycoproteins,
requires their extraction from the mmnbrane. The key-step in this process, the so called "solubilization" of the
membrane, is achieved by using detergents. Moreover, removal of the detergent is necessary for the assay of
ptutein and further investigations. Ideally, the detergent should achieve ma×imum dissimulation of the
rnembrane while mnintaining the enzymic, antigenic or other biological activities of the component extracted.
Therefore, suitable detergents should possess several properties : 1) electrical neutrality, 2) high water
solubility, 3) high critical miccllat concentration (CMC), 4) optical transparency in the UV region where the
presence of proteins is monitored, 5) no side effect in other assays, 6) ease of preparation and cheapness. Very
few comnmicially available detergents meet all these requirements. Some absorb intensely at 280 nm (Triton
XI00, Nonidet P40), others have low CMC values (Tween 20 and 80) or are poor solubilizing agents
(alkylpolyoxyethylenes), or are rather expensive (alkyl [~-glucosides). eB)day, only the N-gluco-N-
t
1
methylalkanamide derivatives seem to encompass r~ost of the properties mentionned above .
The work presented in this report deals with the syn01esis and assessment of a novel class of non-ionic
detergents that fulfill most of the requirements quoted previously. These compounds were obtail,,ed by
telomerization 2.3 of a tris(hydroxymethyl)-acrylamidomethane monomeric unit 1, in the presence of an aIkyl
thin as chain transfer reagent.
The general sn'ucture of these compounds is 2.
CIt 2 - CH
H --(CH-- CH2)n- S- (CH2)nr- CH3
t
I
CO
i
,
CO
I
NH
NH
I
I
C(CH2OII)3
C(CH~OH)3
I
2
1437