Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants

Article abstract of DOI:10.1016/j.tetlet.2021.153113

Three families of anionic sugar-based surfactants bearing a sulfate functional group on the primary position of a monosaccharide were synthesized and their physicochemical properties were compared. The first family corresponds to 6-sulfate derivatives of commercially available octa- and dodecyl β-D-gluco- and galactopyranosides. The second and the third families contain an amide linker between the sulfated monosaccharide (galactose, glucose or xylose) and the hydrophobic alkyl chain. Twelve of the as-synthesized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good ability to reduce surface tension. The obtained results confirm the interest in these new bio-based molecules for potential substitution of anionic surfactants in various formulations.

Full text of DOI:10.1016/j.tetlet.2021.153113

Tetrahedron Letters 74 (2021) 153113
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Synthesis and interfacial properties of new 6-sulfate sugar-based anionic
surfactants
a
b
a
a
a
a
Bemba Abdellahi , Rémy Bois , Sema Golonu , Gwladys Pourceau , David Lesur , Vincent Chagnault ,
b
b
b
a,
⇑
Audrey Drelich , Isabelle Pezron , Alla Nesterenko , Anne Wadouachi
a
Laboratoire de Glycochimie des Antimicrobiens et des Agroressources (LG2A), UMR CNRS 7378, Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne,
3 rue St Leu, FR-80039 Amiens Cedex, France
Université de Technologie de Compiègne, ESCOM, TIMR (Transformations Intégrées de la Matière Renouvelable), Centre de recherche Royallieu, CS60319 - 60203 Compiègne Cedex,
3
b
France
a r t i c l e i n f o
a b s t r a c t
Article history:
Three families of anionic sugar-based surfactants bearing a sulfate functional group on the primary posi-
tion of a monosaccharide were synthesized and their physicochemical properties were compared. The
first family corresponds to 6-sulfate derivatives of commercially available octa- and dodecyl b-D-gluco-
and galactopyranosides. The second and the third families contain an amide linker between the sulfated
monosaccharide (galactose, glucose or xylose) and the hydrophobic alkyl chain. Twelve of the as-synthe-
sized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface
activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants
show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good abil-
ity to reduce surface tension. The obtained results confirm the interest in these new bio-based molecules
for potential substitution of anionic surfactants in various formulations.
Received 22 February 2021
Revised 13 April 2021
Accepted 19 April 2021
Available online 22 April 2021
Keywords:
Anionic surfactant
Carbohydrate
Glycolipid
Interfacial properties
Sulfated sugar
Ó 2021 Elsevier Ltd. All rights reserved.
Introduction
and properties characterization of anionic sugar derivatives; these
molecules showed good adsorption properties similar to other
Sugar-based surfactants are surface-active agents that are gain-
ing more and more attention due to their valuable properties, mak-
ing them interesting for a wide range of applications in industrial
fields such as food, detergents and cosmetics [1]. They exhibit
major advantages regarding their performance, relatively low cyto-
toxicity, higher biodegradability [2–4] and environmental compat-
ibility [5] making them promising alternatives to petroleum-based
surfactants [6].
Compared to other types of surfactants, anionic molecules are
the most consumed on a worldwide scale because of their interest-
ing properties and low cost [7]. Nevertheless, the use of these sur-
factants in cosmetics, detergents and toiletries is limited by their
high skin and eye irritation potential [8]. The development of
new anionic surfactants is an important priority in the field of col-
loid science. To the best of our knowledge, only a limited number
of studies have reported the production of anionic surfactants from
sugars and the characterization of their physicochemical proper-
ties. Among them, several articles have reported the synthesis
ionic surfactants [9].
For example, N-dodecyl-N-(3-propanoate)-b -
D
-glucosylamine
nanoparticles for
enhanced oil recovery [10], as did the derivative with an ethylsul-
showed
a synergetic effect with Ag-TiO
2
fate group on the nitrogen atom of N-dodecyl- b -D-glucosylamine
[11].
The synthesis of sugar-based surfactants with phosphate groups
as hydrophilic moieties, exhibiting surface activities superior to
those of classical surfactants containing only one non-polar or
hydrophobic moiety and one polar head unit, was also described
[12]. As a representative example, dodecyl b -D-glucopyranoside-
6-phosphate has been successfully used as a chiral selector for
the enantiomeric separation of analytes and enantiomers in micel-
lar electrokinetic capillary chromatography [13,14].
Surfactant synthesis involves the combination of a polar head
and a hydrophilic part. A large number of studies have been
focused on the understanding of relationships between the chem-
ical structure of surfactants and their surface properties [15–17].
The main challenge remains their synthesis, in particular the con-
nection of the hydrophilic group (carbohydrate) to the alkyl chain
by a linker. Another challenge is to anticipate the trends between
the sugar-based structure and their properties, to produce greener
⇑
Corresponding author.
E-mail address: anne.wadouachi@u-picardie.fr (A. Wadouachi).
https://doi.org/10.1016/j.tetlet.2021.153113
040-4039/Ó 2021 Elsevier Ltd. All rights reserved.
0

B. Abdellahi, Rémy Bois, S. Golonu et al.
Tetrahedron Letters 74 (2021) 153113
surfactants for specific applications. Sugar-based surfactants, com-
prising of glyco-amides, glyco-esters, glycosides and other deriva-
tives can exhibit various physicochemical properties depending on
their molecular structure.
In previous work [18], we synthesized N-octyl-glycosylamines
(
sugar-NH-CO-R) derived from glucose and maltose, 6-amino-
deoxy-N-octanoyl- -glucose (sugar-NH-CO-R) and N-octyl- -glu-
D
D
curonamide (sugar-CO-NH-R). The surface-active properties of
these nonionic glycolipids (bearing an amide linker) were com-
pared to those of Tween 20 and Hecamed. We observed differ-
Scheme 1. Sulfation of alkyl D-glycopyranosides.
Ò
Some alkyl 6-O-sulfo- b -D-glycopyranosides have previously
ences in their solubility and ability to form micelles as a function
of temperature. They were also evaluated for their cytotoxicity
on mouse fibroblasts with N-acyl-glycosylamines presenting the
lowest cytotoxic effect. The results revealed significant differences
in both the physicochemical properties and cytotoxic effects
depending on structural features, such as the position of the link-
age on the sugar head-group, or the orientation of the amide
linkage.
According to the literature, introduction of an anionic site
should enhance the water-solubility and detergent performance
of the surfactant [19]. Herein, we have introduced a sulfate group
at the primary position of the monosaccharides. Thanks to the
enhanced solubility, we can extend the study to glyco-amide
derivatives bearing a longer (dodecyl) alkyl chain in order to iden-
tify sugar-based surfactants which could be potential candidates
for the replacement of widely used petroleum-based molecules
such as sodium dodecyl sulfate (SDS), sodium laureth sulfate
been reported in the literature. Compound 4 was studied as a
potential inhibitor of trehalose 6-phosphate phosphatase, which
is involved in microbial and nematodal human pathogens [21].
Compound 5 was reported as an effective chiral selector for micel-
lar electrokinetic capillary chromatography resolution of a variety
of enantiomeric mixtures [22]. Its low CMC (1 mM) and its high
hydrosolubility are given as advantages for this application.
The second and third families of sulfated glycolipids involve an
amide linker between the sugar and lipid moieties. Depending on
the direction of this linker, cyclic (N-acyl-6-O-sulfo- b -
D
-glycopy-
ranosylamines) or acyclic (N-alkyl-6-O-sulfo-D-glyconamides)
structures were synthesized.
The preparation of the second family followed a three-step
strategy, with the preparation of a glycosylamine carbamate salt
intermediate [18,23] which was then treated with an acyl choride
and then sulfated at the primary position (Scheme 2).
The carbamate salts of gluco- and galactosylamine were
obtained in good to excellent yields (80–97%). According to the
Plusquellec [24] or Lubineau [25] protocols, subsequent acylation
(
SLES) or sodium dodecylbenzene sulfonate (SDBS).
Results and discussion
gave the corresponding N-acyl b -D-glycopyranosylamines deriva-
tives 11–13 which were directly engaged in the next reaction. As
previously observed, the sulfation led to monosulfated compounds
14–16 as the major products in 54–65% yield. The formation of
disulfated derivatives was also observed as mixture of isomers
which have not been identified. The desired compounds 14–16
were easily purified by reverse phase flash chromatography. These
compounds correspond to cyclic sugar derivatives in which the
sugar is linked by an NH-CO bond to the alkyl chain.
A
library of sulfated glycolipids was prepared following
three main structures: alkyl 6-O-sulfo- b -D-glycopyranosides,
N-acyl-6-O-sulfo- b -
sulfo- -glyconamides. The physicochemical properties of these
anionic glycolipids were compared to those of two commercially
available standard anionic surfactants, sodium laureth sulfate
D-glycopyranosylamines and N-alkyl-6-O-
D
(
SLES) and sodium dodecylsulfate (SDS) (Fig. 1).
First, sulfation of commercially available octyl b -
D
-glucopyra-
The third family is designated as an acyclic sugar with a CO-NH-
linkage between the sugar and the alkyl chain, in which the amide
carbonyl is the anomeric carbon of the sugar (Scheme 3). First,
nucleophilic addition of the alkylamine was carried out on
commercially available glucono- and galactono-1,5-lactone. The
glyconolactone solubilized in methanol (0.42 M) was stirred in
the presence of 1.1 equivalents of octyl- or decylamine until
disappearance of the starting material, giving the corresponding
noside 1, and octyl and dodecyl b -
was carried out using 2 equivalents of SO
D
-galactopyranoside 2 and 3
.pyr according to litera-
3
ture procedures [20]. After purification by reverse flash chromatog-
raphy, the corresponding sulfated glycolipids 4–6 were obtained in
6%, 67% and 63% yield, respectively (Scheme 1). In each case,
small amounts of disulfated glycolipids were observed by reverse
phase TLC (disulfated compound Rf = 0.7, monosulfated compound
7
Rf = 0.3, H
isomers. In the H NMR spectrum, for monosulfated compounds
–6, a downfield shift for the protons of the primary alcohol
4.15 ppm) was observed.
2
O/CH
3
CN 6/4) and isolated as mixtures of inseparable
N-(alkyl)-
D-glyconamide that precipitated from solution and was
1
separated by filtration. These acyclic glyconamides 19–22,
4
(
Fig. 1. General structures of sulfated glycolipids and commercially available
surfactants studied.
Scheme 2. Synthesis of sulfated N-alkyl b -
14–16.
D-glycopyrano-sylamine compounds
2

B. Abdellahi, Rémy Bois, S. Golonu et al.
Tetrahedron Letters 74 (2021) 153113
By comparing the obtained curves for four families of surfac-
tants (sugar-based surfactants and SDS/SLES), it was observed that
the minimum at the break point, corresponding to self-assembling
of molecules, for surfactants with a shorter alkyl chain (C8) occurs
at significantly higher concentration compared to surfactants with
a long chain (C12). This observation can be explained by the
stronger contribution of the hydrophobic forces occurring during
micellization. Surfactants with a longer hydrophobic chain can
self-assemble to form micelles easier and at lower concentration.
This behavior is in agreement with results usually observed for
conventional surfactants [31–34]. Overall, the CMC values of
glycolipids with a C8 chain were between 25.3 and 75.5 mM,
whereas for glycolipids with a C12 chain, the CMC varied from
Scheme 3. Synthesis of sulfated N-octyl and N-dodecyl-
amides derivatives 23–26.
D-gluco- and D-galacton-
obtained in 82–95% yield, were then sulfated following the same
protocol used for the glycoside and glycosylamine derivatives.
The corresponding 6-O-sulfate compounds were obtained in
4
2–69% isolated yield. As previously observed, the disulfate
2
.1 to 10.2 mM. The CMC of 14 GlcNC8S could not be determined
mixtures were separated from the monosulfated compounds by
reverse flash chromatography.
because of its high value and its limited quantity (Table 1). It can
also be noted that the ratio of CMC(C8)/CMC(C12) for different
families of surfactants, except XylCCnS, were of the same order
of magnitude, between compounds 11 and 16. This constant ratio
indicates the systematic and significant effect of the linear alkyl
chain length on the surface-active properties of the synthesized
surfactants, regardless of the structure of the hydrophilic sugar
part. This is comparable to the values of commercially available
anionic surfactants: CMC (sodium octyl sulfate, SOS)/CMC (sodium
dodecyl sulfate, SDS) is 15–16 [35].
For the synthesis of xylonamide derivatives 30 and 31, a prior
oxidation of xylose was carried out in the presence of hydrogen
peroxide catalyzed by gold nanoparticles supported on alumina
under microwave irradiation, as previously described for the syn-
thesis of glycobionate sodium salts [26]. These conditions gave a
good conversion of xylose into sodium xylonate (up to 85%), and
a moderate yield for isolated xylonolactone (51%). The basic condi-
tions used for the oxidation step catalyzed by gold nanoparticles
require subsequent treatment with an acidic resin (Amberlite
The data related to the surface tension at the CMC (cCMC) and
+
IR120 H ). Complete conversion of sodium xylonate into its lactone
the efficiency of surfactant adsorption (pC20) indicate that anionic
glycolipids have high efficiency in lowering the surface tension of
water comparable to commercially available molecules (Table 1).
Surfactants with a long alkyl chain possess higher ability for the
reduction of surface tension of aqueous solutions (higher pC20 val-
ues) compared to those with a short alkyl chain. This assumes that
the energy needed to bring C12 surfactant molecule from the bulk
to the air/water interface is lower. As can be seen, for glycolipids
form is difficult to accomplish, and a mixture of xylonic acid and
xylonolactone was obtained, thus giving a moderate yield for lac-
tone 27 [27].
The aminolysis of 27 with octylamine and dodecylamine in
methanol proceeded at reflux to afford xylonamides 28 and 29 in
7
6% and 65% yield, respectively, which were sulfated following
the general sulfation procedure to afford acyclic 6-sulfate xylon-
amides 30 and 31 in 64% and 69% yield, respectively (Scheme 4).
All of the sulfated compounds were evaluated for their interfa-
cial properties (described in the ESI). The surface-active data are
summarized in Table 1.
with the same hydrophobic chain length, the
cCMC varied notice-
ably. For example, this minimum surface tension changes from
À1
À1
2
8 mN.m (16: GalNC12S) to 43 mN.m (5: GlcOC12S) for C12
surfactants. This variation is undoubtedly related to the structure
of the polar part of the glycolipid (cyclic or open chain sugar)
and the nature of the linker between the hydrophilic and
hydrophobic parts. In fact, the change in flexibility of the hydrophi-
lic part can lead to various molecular configurations of the surfac-
tant. The structure of the surfactant layer adsorbed at the air/water
interface as well as the surface properties is also influenced [36].
If we compare the properties of glycolipids with C12 anionic
commercial surfactants, SLES shows the highest efficacy character-
ized by the lowest CMC. However, several glycolipids bearing a C12
chain (5: b GlcOC12S, 24: GlcCC12S, 26: GalCC12S, 31: XylCC12S)
possess lower CMC values than SDS. Furthermore, according to
the literature, the CMC of sodium octyl sulfate (SOS) is equal to
The most important applications of surfactants are related to
their surface-activity and self-organization in solution. Knowledge
of the adsorption properties allows evaluation of the efficiency and
performance of the surfactant system. The higher the level of sur-
factant performance, the lower the amount that is required and,
consequently, the lower the environmental and economic impact
produced. Detergents with low CMC, low cCMC and strong efficacy
in decreasing surface tension (pC20) are often considered as suit-
able for different applications.
The evolution of equilibrium air/liquid surface tension with
concentration of the studied anionic glycolipids is presented in
Fig. 2. A minimum was observed at the break point of surface ten-
sion-concentration curve for all anionic glycolipids. Usually, the
minimum in surface tension near CMC is related to the presence
of a small amount of residual impurities with amphiphilic proper-
ties participating in the surface tension reduction. For example,
this particularity is often noticed for SDS because of the presence
of residual dodecanol [28,29]. However, some authors claim that
the local minimum of the surface tension is mainly related to the
local maximum of the chemical potential, and does not necessarily
indicate the presence or absence of impurities [30].
1
20 mM [37] which is significantly higher than the CMC values
of anionic glycolipids bearing a C8 chain synthesized in this study.
Regarding the surface tension reduction ( CMC) surfactants 15
GlcNC12S), 24 (GlcCC12S) and 31 (XylCC12S) have similar perfor-
c
(
mance to SDS, whereas 15 (GlcNC12S) and 31 (XylCC12S) possess
equivalent performance to SLES. The data show that for studied
sugar-based anionic surfactants with
a C12 alkyl chain (5:
GlcOC12S, 15: GlcNC12S, 16: GalNC12S, 24: GlcCC12S, 26:
GalCC12S, 31: XylCC12S), the pC20 values are between those of
commercial anionic molecules with the same chain length (SLES
and SDS).
In conclusion, three sugar-based surfactants families, including
nine new sulfated compounds, were synthesized in one or three
steps and then compared with commercially available surfactants.
The synthesized sugar-based anionic surfactants were found to
exhibit interesting surface adsorption properties comparable to
those of commercially available anionic surfactants. As expected,
Scheme 4. Synthesis of sulfated N-octyl and N-dodecyl-
0 and 31.
D-xylonamides derivatives
3
3

B. Abdellahi, Rémy Bois, S. Golonu et al.
Tetrahedron Letters 74 (2021) 153113
Table 1
Physical parameters of surface activity for the studied sugar-based and commercially available reference surfactants SDS and SLES at 25 °C (except for 25 GalCC8S and 26
GalCC12S which were measured at 50 °C).
À1
À1
Compounds
Mw (g.mol
)
CMC (mM)*
c
CMC (mN.m )*
pC20*
SDS
SLES
288
370
8.0 ± 0.5
0.5 ± 0.15
45.2 ± 2.5
4.1 ± 0.4
25.3 ± 1.8
>70
10.0 ± 0.8
9.0 ± 0.6
50.4 ± 2.3
3.0 ± 0.4
43.2 ± 3.0
3.5 ± 0.3
75.5 ± 2.8
2.0 ± 0.3
35 ± 1.3
27 ± 1.8
42 ± 1.5
43 ± 2.5
37 ± 1.7
nd
29 ± 1.2
28 ± 1.2
40 ± 1.9
32 ± 2.8
40 ± 2.1
38 ± 1.7
39 ± 1.7
31 ± 2.2
2.52 ± 0.02
4.40 ± 0.01
1.73 ± 0.1
2.75 ± 0.03
2.27 ± 0.05
nd
2.89 ± 0.02
3.21 ± 0.02
2.52 ± 0.05
3.92 ± 0.05
2.55 ± 0.03
4.3 ± 0.04
1.82 ± 0.07
3.43 ± 0.06
4
5
6
1
1
1
2
2
GlcOC8S
396.4
452.5
396.4
407.4
463.5
463.5
409.4
465.5
409.4
465.5
379.4
436.5
GlcOC12S**
GalOC8S
4 GlcNC8S
5 GlcNC12S
6 GalNC12S
3 GlcCC8S
4 GlcCC12S
2
2
3
3
5 GalCC8S
6 GalCC12S
0 XylCC8S
1 XylCC12S
*
*
Standard deviation of each value corresponds to the precision of the graphical determination of the physicochemical parameter.
À1
*Values in reference [20] are 11.1 mM for CMC, and 34.5 mN.m for
CMC
c .
Fig. 2. Representative curves of surface tension vs. concentration for selected anionic glycolipids. Dotted lines are drawn as a visual guide only. Each point represents the
mean of three measurements. Error bars are smaller than the plot symbols.
the CMC values decreased with the increase in alkyl chain length.
Glycolipids with a longer chain (C12) were characterized by their
higher ability to reduce the surface tension. In addition, the func-
tional properties of three anionic glycolipids (15: GlcNC12S, 24:
GlcCC12S and 31: XylCC12S) were described in our recent study
human skin model. These promising results highlight the interest
in the development and characterization of anionic sugar-based
amphiphiles as potential candidates for the substitution of petro-
leum based anionic surfactants in cosmetic and personal care for-
mulations. Finally, these findings indicate a direction for future
studies, which will focus on the characterization of mono- and
disulfate mixtures, avoiding the separation step during synthesis.
[
38]. These surfactants have good foaming properties comparable
with commercial anionic molecules, and low irritant effect on a
4

B. Abdellahi, Rémy Bois, S. Golonu et al.
Tetrahedron Letters 74 (2021) 153113
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