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The presence of a Paba-linker should avoid decoupling of the amino acids under alkaline conditions
and an excess of sophorolipid ester is used to favor mono-acylation. FTIR analysis revealed that the
sophorolipids are mainly attached to the nanoparticle surface via the carboxylic acid function. No
inhibition was observed for acidic sophorolipids. When Lipase PS is used as catalyst, selective
acylation at the 6??-postion is obtained. Keywords Cheese Whey Hydroxy Fatty Acid Cytochrome
P450 Monooxygenase Candida Bombicola Sophorolipid Production These keywords were added by
machine and not by the authors. No cytotoxicity was observed against healthy peripheral blood
mononuclear cells. Shao et al. described the anticancer activity of different sophorolipid derivatives
against the esophageal cancer cell lines KYSE109 and KYSE450. 35 Diacetylated sophorolipid
lactone displayed the highest activity with complete inhibition of both cell lines at a concentration of
30 ?g mL ?1. MSLs incorporated in this invention also include those that result by performing
multiple modification chemistries on a natural sophorolipid precursor. Deprotection of the different
protecting groups yielded amino acid conjugated sophorolipids 119. The acute toxicity is determined
as the EC 50 after 48 h on Daphnia magna, Tetrahymena terhmophila and Pseudokirchneriella
subcapitata and proved to be ten times higher as compared to conventional surfactants. 4a,12 The
chronic toxicity was determined via a reproduction test on Daphnia magna. Chemical modifications
can also be done following sophorolipid extraction to alter the molecular structure. Particle size
distribution was determined via both transmission electron microscopy (TEM) and dynamic light
scattering measurements (DLS). Additionally, it is contemplated that esters of amino acids and
oligopeptides can be incorporated at the 6. The free carboxylic acid function offers the opportunity
for further derivatization towards polyesters. Diese Ertragssteigerung wurde sowohl in Kombination
mit Aktivstoffen als auch ohne Aktivstoffe erzielt. A specific cultivation experiment to investigate
this was set up as described under the methods and materials section. Christian V. Stevens
(SynBioC, Faculty of Bioscience Engineering) and Prof. Preferred esters are methyl (SLEM), ethyl
(SLEE), and hexyl (SLEH). Different enzymes were evaluated, of which only Novozym 435 was
successful for the formation of sophorolipid amides 95 in high yield. The grain yields of this legume
were weighed after harvesting the culture. His research interest focuses on synthetic heterocyclic
chemistry for agrochemical and medicinal applications, on chemical modification of renewable
resources and on the use of flow chemistry to scale-up organic reactions that are difficult to scale-up
in batch. The doxorubicin loaded nanoparticles performed better then both the sophorolipid-
conjugated nanoparticles and the free doxorubicin chloride 194 against both cell lines. Christian V.
Stevens at the Department of Sustainable Organic Chemistry and Technology. This revealed that the
growth of the mammalian cells was encouraged by the silver nanoparticle studded polyethylene
scaffolds and that the cells exhibited good viability. Improving the statistical power by increasing the
sample size might help if there was an undetected significant difference for the wild type (with and
without the addition of SLs) in this experiment. Multiple modifications of natural sophorolipids have
already been described, but were never combined in one review. The highest activity for the
conversion towards acetylated glucolipid acid 105 was obtained with pectolyase. Within six hours of
exposure, the silver nanoparticle studded polyethylene scaffolds displayed a broad activity against
both the Gram-positive and Gram-negative bacteria. Inedible Jatropha oil can be used as
fermentation feedstock in the production of sophorolipids by S. Diacetylated sophorolipid 17 was
acetylated with acetic anhydride towards the peracetylated sophorolipid 33. Microbial biosurfactants
generally have an amphiphilic structure, possessing a hydrophilic moiety, such as an amino acid,
peptide, sugar or oligosaccharide, and a hydrophobic moiety including saturated or unsaturated lipid
or fatty acids.
The 2-dodecyl sophorolipid 99 was also acylated at the 6?- and 6??-position with the unusual fatty
acids ( R )-3-hydroxy decanoic acid and ( S )-17-hydroxy stearic acid which are obtained via
hydrolysis of respectively rhamnolipids and sophorolipids. The sophorolipid free acid is transformed
into the sophorolipid benzyl ester 106b through esterification with benzyl alcohol. During cultivation
(24 or 48 h), growth was monitored by optical density measurements at 600 nm every 7 h (FLUOstar
OPTIMA FL, BMG Labtech). The fish Lateolabrax japonicas and Paralichthys olivaceus displayed
an EC 50 of respectively 60 and 110 ?g mL ?1 and the relative clearance rate of the mussel Mytilus
edulis decreased to 80% at a sophorolipid concentration of 20 ?g mL ?1. Cross-methathesis with
trans -3-hexene, 1-hexene and ethylene followed by ethanolysis and optional hydrogenation yielded
short-chain alkyl sophorolipids 146 and 147. As little as 25 h after the first metering in of the alcohol
it is possible to detect the novel sophorose lipid in the culture broth by the HPLC technique. This
results in linkage of the monomers via both the 6?-position and the 4??-position at the sugar moiety.
Although a rising pH promotes the solubilization of the precipitated SLs, a LC-MS analysis also
showed that the SL mixture became enriched in more hydrophilic compounds: after 15 days, mono-
acetylated lactonic SLs (24 min) and di-acetylated acidic SLs (23 min) appeared ( Figure 7 b), and
their concentration increased with time ( Figure 7 c: 40 days). Continuous flow synthesis of
sophorolipid-capped silver nanoparticles is described by Kumar et al. 81 Stearic acid based
sophorolipid 10 was used as reducing and capping agent for the continuous flow experiments since
the resulting nanoparticles were formed faster and featured a better size uniformity than those
synthesized with oleic acid based sophorolipid 2. Finally, degradation of the polymers in an
osteogenesis medium was determined. If documents are cited in the context of the present
description, their contents are intended to form part of the disclosure content of the present
invention. After conversion of the ester function of amine 150 into a carboxylic acid function, a
Curtius rearrangement with diphenylphosphorylazide and a Mitsonobu reaction were performed to
yield triamine 153. Moreover, the growth of the publications on sophorolipids has resulted in an
increased number of review articles. Finally, we do not make any chemical modifications—our
product is created only through natural processes. Sophorolipid-capped silver nanoparticles are thus
more effective against Gram-negative bacteria. Acid methanolysis of sophorolipid acids 2 and 10
resulted in the cleavage of fatty acid methyl esters 11 and 12 which were separated via fractional
crystallization. Additionally, due to the amphiphilic nature of biosurfactants, it reduces the interfacial
and surface tension between phases and results in micelle formation. Figure S4: TLC analysis of cell
culture broths of a S. Treatment with 1,2-dibromotetrachloroethane resulted in bromide 178.
Isolation and characterization of ?-glucose tetraacetate derivative 48 demonstrated that the fatty acid
tail is linked to the C4??-position in the diacetylated sophorolipid lactone 37. Gout, Urate, and
Crystal Deposition Disease (GUCDD). For example, in the synthesis of sophorolipid alkyl esters via
alkaline hydrolysis of di-acetylated sophorolipid lactone, the products are precipitated in water after
reaction. He is involved in on-line and off-line analysis of complex petrochemical and biochemical
samples using comprehensive two-dimensional gas chromatography. Years later, lactonic
sophorolipids and lactic acid were studied again for their synergism against L. Copolymers
containing both methacrylate and azide groups were also prepared. Singh et al. investigated the
antibacterial activities of these sophorolipid-capped silver nanoparticles. 80 For sophorolipids as
such, good inhibition was obtained against the Gram-positive bacteria Bacillus subtilis and
Staphylococcus aureus while there was only a faint inhibition against the Gram-negative bacterium
Pseudomonas aeruginosa. Use of sophorolipids according to any one of claims 1 to 5 in
compositions, characterized in that the compositions contain, in addition to sophorolipids, at least
one pesticide which is directed against phytopathogenic organisms, preferably against fungal
organisms. A specific cultivation experiment to investigate this was set up as described under the
methods and materials section. Adsorption studies were performed for the sophorolipid-capped iron
oxide nanoparticles with two lectines, namely Concanavalin A and lectin from Bandeiraea
simplicifolia. Subclasses of glycolipids include rhamnolipids, tehalolipids, and sophorolipids.
No melting transitions were observed for the mono- and non-acetylated sophorolipid polymers,
probably due to the absence of a crystalline phase caused by a restricted chain mobility. Upon
irradiation, sheet-like structures are formed initially which are converted into fully developed
spherical mesostructures after one hour. For example, in the synthesis of sophorolipid alkyl esters via
alkaline hydrolysis of di-acetylated sophorolipid lactone, the products are precipitated in water after
reaction. Only slight differences in the fatty acids in the side chain of the sophorose lipids are found.
The current published data highlights the importance of sophorolipids as natural compounds for
potential application in a wide range of sectors through sustainable technologies. Additionally, the
ability of producing SLs is clearly not sufficient to promote growth on rapeseed oil directly, as the
growth of the wild type is not surpassing that of the SL deficient. As biodegradable biosurfactants
they can be used in environmental protection. A further advantage of the use according to the
invention of the sophorolipids is that the use of pesticides, preferably fungicides, can be omitted
even if a corresponding clinical picture is formed, as is caused by harmful organisms, preferably
fungi, and yet an increase in yield is achieved. Increased mortality was observed for treatment with
purified diacetylated sophorolipid lactones. Sophorolipids also displayed anti-herpes virus activity
for which the Epstein-Bar virus was used as a model organism. 44 The EC 50 values for diacetylated
sophorolipid lactone and sophorolipid acid were respectively 25.8 and 49.2 ?M. Bromination
towards ?-acetobromosophorose 34 was followed by the synthesis of ?-octaacetyl sophorose 35.
Reductive amination with a variety of secondary amines furnished sophorolipid amines 139, which
were subsequently quaternized and deprotected to yield sophorolipid quaternary ammonium salts 140
and 141. C (double bond) in the lactonic and open chain forms. The DPMA assumes no liability for
any errors or omissions. Glycolipid biosurfactants, main classes, functional properties and related
potential applications in environmental biotechnology. Solid-state fermentation for the production of
biosurfactants and their applications. All tested derivatives displayed virus inactivation with EC 50
below 200 ?g mL ?1. A higher antimicrobial activity was observed against S. The antimicrobial
activities of the zinc oxide nanoparticles were evaluated against the Gram-negative bacterium
Salmonella enterica and the fungus Candida albicans. The enzymatic sophorolipid modifications
mostly enable selective transformations at the sugar head, whereas chemical modifications open up a
whole new range of possible sophorolipid analogues. Continuous flow synthesis of sophorolipid-
capped silver nanoparticles is described by Kumar et al. 81 Stearic acid based sophorolipid 10 was
used as reducing and capping agent for the continuous flow experiments since the resulting
nanoparticles were formed faster and featured a better size uniformity than those synthesized with
oleic acid based sophorolipid 2. Proving that several tested genera, next to three ecologically highly
relevant species ( H. alvei, F. fructosus, and Z. rouxii ) are inhibited by SLs correlates with the broad
antimicrobial activity that is needed to favor S. Peaks correspond to di-acetylated lactonic SLs C18:0
(29 min) and C18:1 (27 min), mono-acetylated lactonic SLs (23 and 24 min), di-acetylated acidic SLs
(23 and 24 min), mono-acetylated acidic SLs C18:1 (21 min), non-acetylated acids SLs C18:1 (20
min), and hydroxylated fatty acids (25 and 26 min). Subsequent treatment with silver acetate gave
the corresponding ?-bromosophorose hexaacetate derivative 41. Subsequent ethanolysis reaction
yielded the corresponding ethyl ester 144. It has not to date been possible to use more cost-effective
and more easily obtainable 1-alcohols because it is known that they are to a large extent converted
into the corresponding acids before they are transformed into glycolipids (see, for example, D. F.
Jones, R. Howe, J.Chem.Soc. -C-, (1968), 2801-2808). Figure S6: Scatterplots of the estimated
growth parameters of a sophorolipid deficient S. This is likely due to the higher effective area
occupied by the sophorose group. More broadly, research is needed to involve advanced technologies
in the production and applications of sophorolipids, as well as focus on exploring how sophorolipids
can be produced efficiently based on different production processes. The examples show that the use
of sophorolipids to increase the yield of agricultural crops for a variety of crops is possible.
According to Lachance et al., yeast strains of Starmerella bombicola were originally discovered in
concentrated grape juice in South Africa, suggesting that nectar-feeding insects were most likely
their dominant habitat of survival. Incubation of the lysate with the non-acetylated acidic SLs (19.7
min) for 9 days leads to clear degradation: the biggest peaks appearing correspond to C18:1
glucolipids (21.9 min) and C18:1 hydroxylated fatty acids (26.7 min). Other compounds include
other hydroxylated fatty acids derived from other SL variants present in the substrate, giving rise to
C18:0, C18:2, and C16:0 hydroxylated fatty acids ( Figure 10 a; and Table 3 ). In addition,
biological and physicochemical properties can be affected due to different forms and structures of
sophorolipids. Multiple enzymes were evaluated and the highest conversion was obtained with
Novozym 435. The copolymer composition was controlled by the monomer feed ratio. Amine 158
was also reacted with N -bromosuccinimide and sodium azide towards azide 163 and additionally
subjected to a Staudinger reaction and protection of the amine function towards Fmoc-protected
amine 164. SLs disappeared from the production medium during prolonged incubation and S.
Reaction with bromine delivered the second building block 78. The much higher increase of the
average particle size for the nanoparticles synthesized at room temperature indicated that
sophorolipids were more loosely bonded to the nanoparticle surface. Macrophages which were in
vitro cultured with lipopolysaccharides showed reduced nitrogen oxide production and induced
expression of several cytokines. Starmerella bombicola is the best known and preferred producing
strain with a production yield of more than 400 g L ?1. However, some observations indicate a less
important physiological function of SLs in the growth on hydrophobic substrates. Terminal amine
groups were introduced via an EDC-mediated amidation reaction with ethylenediamine prior to the
coupling of diacetylated sophorolipid acid 6. The anticancer activity of diacetylated sophorolipid
lactone and sophorolipid acid against human pancreatic cancer cells was also evaluated. 34 A
decreasing cytotoxicity of respectively 40.3 to 3.4% and 49 to 0% was observed with increasing
concentration from 500 to 2000 ?g mL ?1. The antimicrobial activities of the zinc oxide nanoparticles
were evaluated against the Gram-negative bacterium Salmonella enterica and the fungus Candida
albicans. Diacetylated sophorolipid 26 was further methylated towards sophorolipid methyl ester 36
and subsequently hydrolyzed into 2,3,4,6-tetra- O -methyl- D -glucose 24 and 3,4,6-tri- O -methyl-
D -glucose 25 which confirmed the 1,2-glycosidic link between the two glucose units. The mixture
of this short-chained sophorolipid acid and azelaic acid reduced the surface tension of water to 30
mN m ?1 and dynamic surface tension measurements indicated that the reduction of the surface
tension was faster compared to crude sophorolipids after fermentation. Methacrylate and butyrate
groups were introduced at the 6?-position through an enzyme-catalyzed acylation of the mono-
acetylated sophorolipid lactone 9 with the respective vinyl acylates. These results were confirmed by
fluorescence spectroscopy. The results show a significant impact of the modified head groups on the
surface tension-lowering properties. A second glucose molecule is linked to the 2?-position of the
first one by a glycosyltransferase II, yielding sophorolipid acid 2. Hydrogenation of unsaturated alkyl
sophorolipid 146 was not performed since this terminal double bond is valuable for further
functionalization. FTIR analysis revealed that the sophorolipids are mainly attached to the
nanoparticle surface via the carboxylic acid function. Critical micelle concentrations were
determined via the Wilhelmy plate method and n -dodecyl-?- D -maltoside was used as a reference
compound for comparison. Subsequently, this glucolipid was acylated at the 6?-position with sebacic
acid towards glucolipid 101. Like synthetic surfactants, biosurfactants are molecules that lower the
surface tension between two materials, either a gas and a liquid (e.g. water surface tension), two
liquids (e.g. water and oil), or a liquid and solid (water and dirt particles). It is reported that
Rhamnolipids show pesticidal activity due to their cell wall penetrating effect. Sophorolipid-capped
silver nanoparticles are thus more effective against Gram-negative bacteria. Upon irradiation, sheet-
like structures are formed initially which are converted into fully developed spherical mesostructures
after one hour. Moreover, SLs are also synthesized when only glucose is present in the medium (see
Figure S1 ).
Sophorolipids also displayed anti-herpes virus activity for which the Epstein-Bar virus was used as a
model organism. 44 The EC 50 values for diacetylated sophorolipid lactone and sophorolipid acid
were respectively 25.8 and 49.2 ?M. Rhamnolipids have been characterized in a recent study as
immunostimulants in plants ( Varnier et al., 2009: Bacterial rhamnolipids are novel MAMPs
conferring resistance to Botrytis cinerea in grapevine. Each species possibly has its own
overwintering strategy. Increasing the chain length results in a higher packing density and lower
minimum surface area, especially from alkyl sophorolipid 146 to alkyl sophorolipid 147a. It is also
defined by the contents of the patent claims. Similar antibacterial potentials were demonstrated by
Chen et al. The structure of a lactonic ( a ) and an acidic ( b ) sophorolipid (SL), produced by
(amongst others) Starmerella bombicola. Deacetylation at the 6??-position resulted in the formation
of 1,6??-sophorolipid lactone 88 (9%) and its 6?-acetylated analogue (14%) ( Scheme 11 ). The
aquatic toxicity is subdivided in acute and chronic toxicity. A second HPLC-MS method was used
for sophorose detection. The pH of the culture suspension decreases over the entire range of
cultivation. In this experiment, after treatment in the untreated controls, there was a moderate to
severe attack with various diseases of the barley, which were also scored at different times. No
growth inhibition was observed against the Gram-negative bacteria Escherichia coli and
Pseudomonas aeruginosa, the fungi Eurotium repens, Mycotypha microspora and Ustilago maydis,
and against the alga Chlorella fusca. Acid methanolysis of sophorolipid acids 2 and 10 resulted in the
cleavage of fatty acid methyl esters 11 and 12 which were separated via fractional crystallization.
The capacity of the three polymers to support the differentiation of the mesenchymal stem cells to an
osteoblast cell phenotype was evaluated, giving the best results for butyrated sophorolipid polymer
130c compared to the control TCPS. Multiple modifications of natural sophorolipids have already
been described, but were never combined in one review. The esterified derivatives 118 are more
potent than the corresponding non-esterified compounds 119. The fungicide Fung-5 had no
influence on these parameters. A higher antimicrobial activity was observed against S. All
hydrophobic carbon sources are converted into fatty acids, which contain in general 16 or 18 carbon
atoms with one or more double bonds. Besides moisturizing and skin-conditioning properties,
sophorolipid lactones proved active to eliminate dandruff. 16 Moreover, sophorolipids proved to
possess desquamating, depigmenting and melanogenesis inhibiting activity. 17 The desquamation is
achieved by detachment of the corneocytes and offers opportunities for the use of sophorolipids
against acne and as an anti-wrinkle product. No inhibition was observed for acidic sophorolipids. Use
of sophorolipids according to one of claims 1 to 3, characterized in that the sophorolipids are used in
dosages of 0.1 to 5 g, preferably 0.5 to 3 g, particularly preferably 0.7 to 1.5 g of active component
per kilogram of seed become. These studies have mainly involved the selective feeding of different
lipophilic substrates. The first question could be solved by performing proteomic studies combined
with knocking out the suspected genes. Antimicrobial activities of the derivatives were also
evaluated. It was observed that particle size decreased with increasing temperature and longer time is
needed at low temperatures to obtain complete particle formation and growth. An advantage of the
use according to the invention of sophorolipids is that yield increases in agricultural crops are
achieved even if the plant pathogen is not combated, or the clinical picture is not changed.
Additionally, inclusive of this invention are amides bearing at the sophorose head group ionic
moieties such as sulfate, sulfonate, phosphate, carboxylate and quarternary ammonium salts that
result in cationic or anionic charged head groups. Therefore, sophorolipids appear to be promising
compounds that can be used in substituting the usage of chemical surfactants in different industries
due to being Earth-friendly and safe for human use.
The disease infestation in% of each leaf is the sum of the infestation by both diseases. This fatty acid
could be used as a building block for the synthesis of pharmaceutically valuable products and for
polyester- and macrocyclic lactones. When Lipase PS is used as catalyst, selective acylation at the
6??-postion is obtained. After transformation towards sophorolipid esters 86d and 86e or
sophorolipid acid 2, the hydroxyalkyl-etherified sophorolipid esters 109 and 110 were produced
through reaction with alkylene oxides in the presence of an alkali catalyst. Growth evaluations were
made 21 days after application - during these 21 days the plants were in the above climatic chambers.
To investigate this, a prolonged combined production and catabolization experiment was performed:
S. Visit our dedicated information section to learn more about MDPI. No statement is made about
the production of biomass or fruit yield. When Fe 3 O 4 nanoparticles were added during the
synthesis, sophorolipid mesostructures embedded with iron oxide nanoparticles were obtained. Three
different ruthenium-based Grubbs catalysts were evaluated and the highest yields were obtained
with catalyst 128. These can be further categorized based chemical structure. Journal of Theoretical
and Applied Electronic Commerce Research (JTAER). The free carboxylic acid function offers the
opportunity for further derivatization towards polyesters. Glycosylation of the acetate protected
derivative 189a selectively led to ?-anomer 190a. These results thus not only affirm the
catabolization of SLs by S. By sophorolipidic acid (SLA) is meant the sophorose-fatty acid
conjugates having a free acid group. Inverting this rationale, one could theoretically imply a relief of
osmotic stress: the osmotically active, highly soluble, low molecular weight sugars outside the cell are
converted into high molecular weight and less soluble SLs, thereby alleviating the osmotic pressure
on the microbial cell. The ring-opening reaction of ( S )-propenoxide with Grignard reagent 68
yielded the enantiomerically pure alcohol 69. After drying, the sophorolipid mesostructures could
easily be redispersed in water. Sophorose is an unusual disaccharide that consists of two glucose
molecules linked ?-1,2. This lactone was subsequently used for the regioselective esterification at the
6?-position of the sugar head, yielding the monoacrylated sophorolipid lactone 89. The unsaturated
methyl ester 11 was oxidized with potassium permanganate and sodium periodate into azelaic acid
14 and 8-hydroxy-pelargonic acid 15, which enabled the determination of the double bond. He is a
former Fulbright Research Scholar of MIT and directs the Pilot plant for steam cracking and
pyrolysis. There have merely been indications of how to obtain these substances, which have never
been isolated or characterized in detail (Davila, A.-M., Marchal, R., Vandecasteele, J.-P., J. lndustr.
Microbiol., (1994) 249-257). This compound was also hydrogenated to the saturated sophorolipid N
?, N ?-dimethylethylamide 122 and subsequently quaternized to the saturated sophorolipid
quaternary ammonium salt 123. In New and Future Developments in Microbial Biotechnology and
Bioengineering. However, the possible enzymatic cleavage of the released sophorose could lead to an
underestimation of the total release of this disaccharide in the assays. Sophorolipids (SL) according
to the invention are mixtures of substances as set forth above. They have mild bactericidal effects,
inhibit the activity of lipase, and stimulate collagen synthesis, making them ideal for use in skincare
products. This adsorption behavior on hydrophilic solids is similar to that of sugar-based nonionic
surfactants and unlike that of nonionic ethoxylated surfactants.
Preferably, these application compositions are prepared by diluting the delivery compositions with
water. Therefore, the starting product was subjected to alkaline hydrolysis with sodium alkoxides,
yielding sophorolipid esters 86. An allylic substitution was used to introduce an amine function at
the allylic position of the double bond. The solid-state properties of this poly(sophorolipid) were
evaluated by Zini et al. 69 Both cis and trans double bonds are present in the poly(sophorolipid),
respectively in 90% and 10%. PhD-thesis, Faculty of Bioscience Engineering, Ghent University,
Ghent, Belgium. The culture is carried out under unchanged conditions between and after the
additions of the substrates. Additionally, the ability of producing SLs is clearly not sufficient to
promote growth on rapeseed oil directly, as the growth of the wild type is not surpassing that of the
SL deficient. A control was maintained for each bacterial culture without adding MSL into the
culture medium. This compound was also hydrogenated to the saturated sophorolipid N ?, N ?-
dimethylethylamide 122 and subsequently quaternized to the saturated sophorolipid quaternary
ammonium salt 123. The aquatic toxicity is subdivided in acute and chronic toxicity. Only di-
acylated sophorolipid 102 and the mixture of mono-acylated sophorolipid 103 and di-acylated
sophorolipid 104 showed inhibition against the Gram-positive bacteria Staphylococcus capitis.
Particle size distribution was determined via both transmission electron microscopy (TEM) and
dynamic light scattering measurements (DLS). After conversion of the ester function of amine 150
into a carboxylic acid function, a Curtius rearrangement with diphenylphosphorylazide and a
Mitsonobu reaction were performed to yield triamine 153. Sophorolipids (SL) according to the
invention are mixtures of substances as set forth above. On the other hand, several laboratory tools
were developed over the past decade, gradually turning S. Subsequent treatment with silver acetate
gave the corresponding ?-bromosophorose hexaacetate derivative 41. No melting transitions were
observed for the mono- and non-acetylated sophorolipid polymers, probably due to the absence of a
crystalline phase caused by a restricted chain mobility. Esterification of sophorolipids is achieved by
alcoholysis of natural sophorolipid mixtures. As one illustrative example, the cross metathesis of
lactonic sophorolipid with vinyl acrylate will produce a diester wherein each of the ester groups can
be converted into the corresponding amide derivative (Scheme 2). Peracetylation towards acetal 76
was followed by selective deprotection of the anomeric centre yielding reducing sugar 77. Acidolytic
or hydrogenolytic deprotection yields the water-soluble sophorolipids 108 with charged head groups.
C22) compared with conventional products while reducing the surface tension of water to a greater
extent. Microbial biosurfactants generally have an amphiphilic structure, possessing a hydrophilic
moiety, such as an amino acid, peptide, sugar or oligosaccharide, and a hydrophobic moiety
including saturated or unsaturated lipid or fatty acids. This procedure is familiar to the person skilled
in the art. Veresterungsreagenzien sind dem Fachmann bekannt, z. B. Saureanhydride, Saurechloride
oder aktivierte Sauren. The infestation in the completely untreated control was also scored. For di-
acetylated lactonic SLs, extracellular conversion into di-acetylated acidic and mono-acetylated
lactonic SLs was detected after 10 days (both compounds co-eluted at 23.4 min; see Figure 8 b). All
these intermediates already appeared after only 24 h of incubation, but the effects became more
pronounced upon longer incubation. A higher antimicrobial activity was observed against S. On
larger scale, physical separation methods such as centrifugation are applied for the isolation.