Lipase catalyzed solid phase synthesis of sugar fatty acid esters:
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| Format: | Thesis Book |
| Language: | English |
| Published: |
1997
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIX, 167 S. graph. Darst. |
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| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV011613438 | ||
| 003 | DE-604 | ||
| 007 | t| | ||
| 008 | 971106s1997 xx d||| m||| 00||| engod | ||
| 016 | 7 | |a 952056402 |2 DE-101 | |
| 035 | |a (OCoLC)49863852 | ||
| 035 | |a (DE-599)BVBBV011613438 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-91 |a DE-355 |a DE-188 | ||
| 100 | 1 | |a Cao, Linqiu |d 1964- |e Verfasser |0 (DE-588)115826491 |4 aut | |
| 245 | 1 | 0 | |a Lipase catalyzed solid phase synthesis of sugar fatty acid esters |c von Linqiu Cao |
| 246 | 1 | 3 | |a Lipase-catalyzed solid phase synthesis of sugar fatty acid esters |
| 264 | 1 | |c 1997 | |
| 300 | |a XIX, 167 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |a Stuttgart, Univ., Diss., 1997 | ||
| 650 | 0 | 7 | |a Festphasentechnik |0 (DE-588)4154192-3 |2 gnd |9 rswk-swf |
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| _version_ | 1823773596630122496 |
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| adam_text |
XII
CONTENT
ACKNOWLEDGEMENT
.
ILL
ABSTRACT
.
IV
ZUSAMMENFASSUNG
.
VI
ABBREVIATIONS
.
XVII
1.
INTRODUCTION
.
1
1.1
SUGAR
FATTY
ACID
ESTERS
OCCURRENCE,
IMPORTANCE
AND
APPLICATIONS
.
1
1.2
FUNCTION,
STRUCTURE
AND
CLASSIFICATION
OF
BIOSURFACTANTS
.
2
1.3
PROPERTIES
AND
CHARACTERISTIC
PARAMETERS
OF
SUGAR
FATTY
ACID
ESTERS
.
5
1.4
DEVELOPMENT
AND
PROBLEMS
IN
THE
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
7
1.4.1
GENERAL
CONSIDERATION
.
7
1.4.2
ENZYMATIC
METHODS
FOR
THE
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
9
1.4.2.1
ACYLATION
OF
NON-MODIFIED
SUGARS
.
9
1.4.2.2
ACYLATION
OF
MODIFIED
SUGARS
.
13
1.5
TARGET
.
17
2.
THEORETICAL
BASIS
OF
ENZYMATIC
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
18
2.1
GENERAL
CONSIDERATIONS
.
18
2.1.1
LIPASES
USED
FOR
THE
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
18
2.1.2
MECHANISM
OF
LIPASE-CATALYSED
REACTIONS
.
21
2.1.3
METHODS
FOR
IRREVERSIBLE
ENZYMATIC
REACTIONS
.
23
2.1.3.1
SOLVENT
EFFECTS
ON
THE
EQUILIBRIUM
POSITION
.
24
2.1.3.2
REMOVAL
OF
THE
PRODUCTS
.
24
2.1.3.3
MODIFICATION
OF
LIPASES
.
25
2.2
KINETICS
OF
LIPASE-CATALYSED
ESTERIFICATIONS
.
25
2.3
IMMOBILISATION
OF
ENZYMES
.
27
2.3.1
GENERAL
CONSIDERATION
.
27
2.3.2
IMMOBILISATION
METHODS
.
28
2.3.2.1
NONCOVALENT
BINDING
.
29
2.3.2.2
COVALENT
BINDING
.
29
2.3.2.3
PHYSICAL
ENTRAPMENT
.
30
3.
ENZYMATIC
REACTIONS
IN
NONCONVENTIONAL
MEDIA
.
31
3.1
GENERAL
CONSIDERATIONS
.
31
3.2
ENZYMATIC
REACTION
SYSTEMS
.
32
XIN
3.2.1
AQUEOUS-ORGANIC
SOLVENT
MIXTURES
(MONOPHASIC)
.
32
3.2.2
AQUEOUS-ORGANIC
TWO
PHASE
SYSTEMS
.
33
3.2.3
ANHYDROUS
ORGANIC
SOLVENTS/SOLID
ENZYMES
(MICROAQUEOUS
ORGANIC
SOLVENTS)
.
33
3.2.4
SOLVENT-FREE
SYSTEM
.
34
3.2.5
SOLID
PHASE
REACTION
SYSTEMS
.
34
3.2.6
SUPERCRITICAL
FLUIDS
.
35
3.2.7
GAS/SOLID
ENZYME
SYSTEM
.
35
3.3.
CRITERIA
FOR
THE
CHOICE
OF
ORGANIC
SOLVENTS
.
36
3.4.
MASS
TRANSFER
IN
ORGANIC
REACTION
MEDIA
.
37
3.4.1
GENERAL
CONSIDERATION
.
37
3.4.2
MASS-TRANSFER
IN
DIFFERENT
REACTION
SYSTEMS
.
38
3.4.2.1
ONE
PHASE
SYSTEMS
.
38
3.4.2.2
TWO
PHASE
SYSTEMS
.
38
3.4.2.3
HETEROGENEOUS
MIXTURE
OF
SUBSTRATES
.
39
3.4.2.3.1
SOLID
SUBSTRATES
AND
SOLID
PRODUCTS
.
39
3.4.2.3.2
TWO
IMMISCIBLE
LIQUIDS/INSOLUBLE
ENZYME
PARTICLES
.
40
4.
RESULTS
.
41
4.1
GENERAL
CONSIDERATIONS
.
41
4.2
SOLUBILITIES
AND
SOLUBILISATION
.
42
4.2.1
SOLUBILITIES
OF
FREE
SUGARS
AND
SUGAR
FATTY
ACID
ESTERS
.
42
4.2.2
SOLUBILISATION
RATE
AND
REACTION
RATE
.
45
4.3
SCREENING
OF
LIPASES
.
48
4.3.1
SCREENING
OF
FREE
LIPASES
.
48
4.3.2
SCREENING
OF
IMMOBILISED
LIPASES
.
50
4.4
ADJUVANT
.
53
4.4.1
SCREENING
OF
ADJUVANTS
.
53
4.4.2
OPTIMUM
ADJUVANT
CONCENTRATIONS
.
55
4.4.3
SOLIDIFICATION
OF
REACTION
MIXTURES
.
58
4.4.3.1
INFLUENCE
OF
ADJUVANTS
.
58
4.4.3.2
INFLUENCE
OF
ADJUVANT
CONCENTRATIONS
.
59
4.4.3.3
INFLUENCE
OF
FATTY
ACIDS
.
60
4.4.3.4
CRYSTALLISATION
OF
THE
PRODUCT
DURING
THE
REACTION
.
61
4.4.4
APPLICATION
OF
COLD
CRYSTALLISATION
TECHNIQUE
FOR
THE
SOLID
PHASE
SYNTHESIS
.
62
4.5
OPTIMUM
SUBSTRATE
RATIO
.
63
4.6
ACYL
DONORS
.
64
4.6.1
FATTY
ACIDS
.
64
4.6.2
COMPARISON
OF
DIFFERENT
ACYL
DONORS
.
66
4.7
ACYL
ACCEPTORS
.
68
XIV
4.8
REGIOSELECTIVITY
.
69
4.8.1
INFLUENCE
OF
LIPASES
.
69
4.8.2
SELECTIVITY
BY
USING
DIFFERENT
SUGARS
.
71
4.8.2.1
PYRANOSE
.
71
4.8.2.2
SUGAR
OR
SUGAR
ALCOHOLS
WITH
TWO
OR
MORE
PRIMARY
HYDROXYL
GROUPS
.
73
4.8.3.
SELECTIVITY
OF
FRUCTOSE
BY
USING
DIFFERENT
ACYL
DONORS
.
74
4.8.4
SELECTIVITY
BY
USING
DIFFERENT
ADJUVANTS
.
75
4.9
IMMOBILISATION
OF
LIPASES
.
76
4.9.1
INFLUENCE
OF
SUPPORT
PROPERTIES
.
76
4.9.2
INFLUENCE
OF
ENZYME
CONCENTRATION
.
77
4.9.3
INFLUENCE
OF
SURFACTANTS
ON
THE
ADSORPTION
OF
LIPASE
ONTO
THE
SUPPORT
.
78
4.10
INFLUENCE
OF
THE
REACTION
TEMPERATURE
.
79
4.10.1
RELATIONSHIP
BETWEEN
TEMPERATURE
AND
CONVERSIONS
.
79
4.10.2
EFFECT
OF
TEMPERATURE
ON
PRODUCT
SOLUBILITY
AND
INHIBITION
.
80
4.11
OPTIMUM
ENZYME
CONCENTRATION
.
82
4.12
ENZYME
STABILITY
.
83
4.12.1
INFLUENCE
OF
FATTY
ACIDS
.
83
4.12.2
INFLUENCE
OF
TEMPERATURES
.
86
4.12.3
INFLUENCE
OF
ADJUVANTS
.
86
4.12.4
OPERATIONAL
STABILITY
.
87
4.13
FURTHER
OPTIMISATION
INVESTIGATION
.
88
4.13.1
INFLUENCE
OF
WATER
ACTIVITY
.
88
4.13.2
INFLUENCE
OF
WATER
MIMICS
.
89
4.13.3
WATER
BINDING
MATERIALS
.
91
4.14
SURFACTANT
PROPERTIES
OF
SUGAR
FATTY
ACID
ESTERS
.
93
4.14.1
HYDROPHILIC-LIPOPHILIC
BALANCE
(HLB)
.
93
4.14.1.1
HLB-VALUE
OF
MONOACYLATED
MONOSACCHARIDE
FATTY
ACID
ESTERS
.
93
4.14.1.2
HLB
VALUES
OF
DIACYLATED
SUGAR
FATTY
ACID
ESTERS
.
94
4.14.2
DETERMINATION
OF
CRITICAL
MICELLAR
CONCENTRATION
(CMC)
.
95
4.14.2.1
SURFACE
TENSION
.
95
4.14.2.2
DETERMINATION
OF
CRITICAL
MICELLAR
CONCENTRATION
(CMC)
.
97
4.14.2.3
COMPARISON
OF
CMC-VALUE
AND
STRUCTURE
OF
SUGAR
FATTY
ACID
ESTER
.
98
4.15
LIPASE-MEDIATED
HYDROLYSIS
OF
SUGAR
FATTY
ACID
ESTERS
.
100
4.15.1
GENERAL
CONSIDERATION
.
100
4.15.2
SCREENING
OF
LIPASE
FOR
THE
HYDROLYSIS
OF
SUGAR
FATTY
ACID
ESTERS
.
100
4.15.3
IMMOBILISATION
OF
LIPASE
FOR
THE
USE
IN
LIPID
RECONSTITUTION
.
101
5.
DISCUSSION
.
103
5.1
GENERAL
DISCUSSION
.
103
XV
5.2
SOLUBILITIES
.
105
5.3
SOLUBILISATION
RATE
AND
REACTION
RATE
.
106
5.4
ADJUVANT
.
107
5.5
LIPASES
.
108
5.6
SUGARS
.
110
5.7
ACYL
DONORS
.
ILL
5.8
INFLUENCE
OF
SUBSTRATE
RATIO
.
ILL
5.9
REGIOSELECTIVITY
.
112
5.9.1
INTERACTION
OF
SUBSTRATES
AND
LIPASE
.
112
5.9.2
INTERACTION
OF
LIPASE
AND
ADJUVANTS
.
113
5.9.3
INTERACTION
BETWEEN
THE
SUBSTRATES
AND
SOLUBILITIES
OF
THE
PRODUCT
.
114
5.10
WATER,
WATER
MIMICS
AND
DRYING
AGENTS
.
115
5.11
ENZYME
STABILITY
.
115
5.12
ADVANTAGES
OF
LIPASE-CATALYSED
SOLID
PHASE
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
117
5.13
SUMMARY
.
118
6.
MATERIALS
AND
METHODS
.
120
6.1
CHEMICALS
.
120
6.1.1
SUGARS
.
120
6.1.2
FATTY
ACIDS
AND
OTHER
ACYL
DONORS
.
121
6.1.3
ORGANIC
SOLVENTS
.
121
6.1.4
MISCELLANEOUS
CHEMICALS
.
123
6.2
EQUIPMENTS
.
124
6.3
SCREENING
OF
LIPASES
.
126
6.3.1
SCREENING
OF
FLEE
AND
IMMOBILISED
LIPASES
.
126
6.3.2
SCREENING
OF
LIPASE
FOR
THE
HYDROLYSIS
OF
SUGAR
FATTY
ACID
ESTERS
.
128
6.3.3
SCREENING
OF
IMMOBILISED
LIPASES
FOR
THE
HYDROLYSIS
OF
SUGAR
FATTY
ACID
ESTERS
.
129
6.3.4
DETERMINATION
OF
HYDROLYTIC
ACTIVITY
OF
LIPASES
.
129
6.3.5
DETERMINATION
OF
SYNTHETIC
ACTIVITY
OF
IMMOBILISED
LIPASES
.130
6.4
DETERMINATION
OF
SOLUBILITY,
SOLUBILISATION
RATE
AND
REACTION
RATE
.
130
6.4.1
DETERMINATION
OF
THE
SOLUBILITY
OF
SUGARS
.
130
6.4.2
DETERMINATION
OF
THE
SOLUBILITY
OF
THE
SUGAR
FATTY
ACID
ESTERS
.
130
6.4.3
DETERMINATION
OF
THE
SOLUBILISATION
RATE
.
130
6.4.4
DETERMINATION
OF
THE
REACTION
RATE
IN
A
SOLUTION
SATURATED
WITH
GLUCOSE
.
131
6.5
DETERMINATION
OF
SATURATION
CONCENTRATIONS
OF
SUGAR
FATTY
ACID
ESTERS
.
131
6.6
SCREENING
OF
WATER
BINDING
MATERIALS
.
131
6.7
INVESTIGATION
OF
ENZYME
STABILITY
.
132
6.7.1
ENZYME
STABILITY
BY
USING
DIFFERENT
FATTY
ACIDS
.
132
6.7.2
ENZYME
STABILITY
BY
USING
DIFFERENT
ADJUVANTS
.
132
XVI
6.7.3
ENZYME
STABILITY
AT
DIFFERENT
REACTION
TEMPERATURES
.
132
6.7.4
OPERATIONAL
STABILITY
OF
IMMOBILISED
LIPASE
.
133
6.8
ENZYMATIC
REACTIONS
.
133
6.8.1
GENERAL
PROCEDURES
FOR
ENZYMATIC
REACTIONS
.
133
6.8.2
GENERAL
PROCEDURES
FOR
PREPARATIVE
SYNTHESIS
OF
SUGAR
FATTY
ACID
ESTERS
.
133
6.9
TLC-ANALYSIS
.
134
6.10
HPLC-ANALYSIS
.
134
6.11
NMR-SPECTRA
.
134
6.12
GENERAL
PROCEDURE
FOR
THE
PURIFICATION
OF
SUGAR
FATTY
ACID
ESTERS
.
135
6.12.1
GLUCOSE
FATTY
ACID
ESTERS
.
136
6.12.2
FRUCTOSE,
MANNOSE,
SORBITOL
AND
MANNITOL
FATTY
ACID
ESTERS
.
136
6.13
IMMOBILISATION
OF
LIPASES
.
136
6.13.1
DEPOSITION
OF
LIPASES
ON
CELITE
AND
HYFLO-SUPER-CEL
.
136
6.13.2
ADSORPTION
OF
LIPASE
ON
EP
100
AND
AMBERLITE
XAD-7
.
136
6.13.3
IMMOBILISATION
OF
LIPASE
ON
ACTIVATED
SILICA
GEL
.
137
6.13.4
MODIFICATION
OF
LIPASE
B
WITH
ACTIVATED
PEG
.
137
6.13.5
IMMOBILISATION
OF
LIPASE
ON
MAGNETIC
POLYPROPYLENE
POLYMER
.
137
6.13.6
IMMOBILISATION
OF
LIPASE
ON
ANION-EXCHANGE
RESIN
.
138
6.14
ADJUSTMENT
OF
WATER
ACTIVITY
.
139
6.15
DETERMINATION
OF
WATER
CONTENT
.
139
6.16
DETERMINATION
OF
AQUAPHILICITY
.
140
6.17
DETERMINATION
OF
HYDROLYTIC
ACTIVITY
OF
LIPASES
.
140
6.18
DETERMINATION
OF
SURFACE
TENSION
AND
CRITICAL
MICELLAR
CONCENTRATIONS
.
141
6.19
DETERMINATION
OF
MELTING
POINTS
.
141
6.20
CHARACTERISATION
OF
SUGAR
FATTY
ACID
ESTERS
.
141
6.20.1
GLUCOSE
FATTY
ACID
ESTERS
.
141
6.20.2
FRUCTOSE
FATTY
ACID
ESTERS
.
147
620.3
MANNOSE
FATTY
ACID
ESTERS
.
148
6.20.4
SUGAR
ALCOHOL
FATTY
ACID
ESTERS
.
149
7.
REFERENCES
.
152
CURRICULUM
VITAE
.
167 |
| any_adam_object | 1 |
| author | Cao, Linqiu 1964- |
| author_GND | (DE-588)115826491 |
| author_facet | Cao, Linqiu 1964- |
| author_role | aut |
| author_sort | Cao, Linqiu 1964- |
| author_variant | l c lc |
| building | Verbundindex |
| bvnumber | BV011613438 |
| ctrlnum | (OCoLC)49863852 (DE-599)BVBBV011613438 |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV011613438 |
| illustrated | Illustrated |
| indexdate | 2025-02-11T15:00:37Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-007822977 |
| oclc_num | 49863852 |
| open_access_boolean | |
| owner | DE-91 DE-BY-TUM DE-355 DE-BY-UBR DE-188 |
| owner_facet | DE-91 DE-BY-TUM DE-355 DE-BY-UBR DE-188 |
| physical | XIX, 167 S. graph. Darst. |
| publishDate | 1997 |
| publishDateSearch | 1997 |
| publishDateSort | 1997 |
| record_format | marc |
| spelling | Cao, Linqiu 1964- Verfasser (DE-588)115826491 aut Lipase catalyzed solid phase synthesis of sugar fatty acid esters von Linqiu Cao Lipase-catalyzed solid phase synthesis of sugar fatty acid esters 1997 XIX, 167 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Stuttgart, Univ., Diss., 1997 Festphasentechnik (DE-588)4154192-3 gnd rswk-swf Lipasen (DE-588)4167788-2 gnd rswk-swf Enzymkatalyse (DE-588)4152480-9 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Zuckertensid (DE-588)4486434-6 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Zuckertensid (DE-588)4486434-6 s Chemische Synthese (DE-588)4133806-6 s Enzymkatalyse (DE-588)4152480-9 s Lipasen (DE-588)4167788-2 s Festphasentechnik (DE-588)4154192-3 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007822977&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Cao, Linqiu 1964- Lipase catalyzed solid phase synthesis of sugar fatty acid esters Festphasentechnik (DE-588)4154192-3 gnd Lipasen (DE-588)4167788-2 gnd Enzymkatalyse (DE-588)4152480-9 gnd Chemische Synthese (DE-588)4133806-6 gnd Zuckertensid (DE-588)4486434-6 gnd |
| subject_GND | (DE-588)4154192-3 (DE-588)4167788-2 (DE-588)4152480-9 (DE-588)4133806-6 (DE-588)4486434-6 (DE-588)4113937-9 |
| title | Lipase catalyzed solid phase synthesis of sugar fatty acid esters |
| title_alt | Lipase-catalyzed solid phase synthesis of sugar fatty acid esters |
| title_auth | Lipase catalyzed solid phase synthesis of sugar fatty acid esters |
| title_exact_search | Lipase catalyzed solid phase synthesis of sugar fatty acid esters |
| title_full | Lipase catalyzed solid phase synthesis of sugar fatty acid esters von Linqiu Cao |
| title_fullStr | Lipase catalyzed solid phase synthesis of sugar fatty acid esters von Linqiu Cao |
| title_full_unstemmed | Lipase catalyzed solid phase synthesis of sugar fatty acid esters von Linqiu Cao |
| title_short | Lipase catalyzed solid phase synthesis of sugar fatty acid esters |
| title_sort | lipase catalyzed solid phase synthesis of sugar fatty acid esters |
| topic | Festphasentechnik (DE-588)4154192-3 gnd Lipasen (DE-588)4167788-2 gnd Enzymkatalyse (DE-588)4152480-9 gnd Chemische Synthese (DE-588)4133806-6 gnd Zuckertensid (DE-588)4486434-6 gnd |
| topic_facet | Festphasentechnik Lipasen Enzymkatalyse Chemische Synthese Zuckertensid Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007822977&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT caolinqiu lipasecatalyzedsolidphasesynthesisofsugarfattyacidesters |