Modularisation of novel multi-enzyme cascades and synthesis strategy development
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| 008 | 200827s2019 gw a||| m||| 00||| eng d | ||
| 015 | |a 20,H06 |2 dnb | ||
| 020 | |c Broschur | ||
| 035 | |a (OCoLC)1157256371 | ||
| 035 | |a (DE-599)DNB1207482595 | ||
| 040 | |a DE-604 |b ger |e rda | ||
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| 049 | |a DE-355 |a DE-83 | ||
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| 084 | |a 660 |2 sdnb | ||
| 100 | 1 | |a Fischöder, Thomas |e Verfasser |0 (DE-588)1202357113 |4 aut | |
| 245 | 1 | 0 | |a Modularisation of novel multi-enzyme cascades and synthesis strategy development |c vorgelegt von Thomas Fischöder (M. Sc.) Biotechnologie |
| 264 | 1 | |a Aachen |c [2019] | |
| 300 | |a XIV, 215 Seiten |b Illustrationen, Diagramme |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c RWTH Aachen University |d 2019 | ||
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 856 | 4 | 2 | |m B:DE-101 |q application/pdf |u https://d-nb.info/1207482595/04 |3 Inhaltsverzeichnis |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032280072&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-032280072 | |
Datensatz im Suchindex
| _version_ | 1819772025426673664 |
|---|---|
| adam_text | CHAPTER
1:
INTRODUCTION
......................................................................................................
-1
-
1.1
CARBOHYDRATES,
GLYCANS
AND
GLYCOCONJUGATES:
CARRIER
OF
COMPLEX
3D
INFORMATION
PATTERN
............................................................................................
-
2
-
1.2
LELOIR-G
LYCOSYITRANSFERASES
:
VALUABLE
CONSTRUCTORS
OF
DIVERSITY
.......................
-
5
-
1.3
NUCLEOTIDE
SUGARS:
THE
ESSENTIAL
BUILDING
BLOCKS
............................................
-
8
-
1.4
MODULAR
DESIGN:
A
POWERFUL
CONCEPT
...............................................................
-11-
1.5
GALECTINS:
IMPORTANT
MEDIATORS
AND
DECODER
OF
THE
GLYCO-INFORMATION
PATTERN
.............................................................................................................
-11
-
1.6
HMOS:
SO
MUCH
MORE
THAN
JUST
NUTRITION
........................................................
-13-
1.7
AIMS
AND
OUTLINE
OF
THIS
THESIS
..........................................................................
-17
-
1.8
REFERENCES
.......................................................................................................
-19-
CHAPTER
2:
REPETITIVE
BATCH
MODE
FACILITATES
ENZYMATIC
SYNTHESIS
OF
THE
NUCLEOTIDE
SUGARS
UDP-GAL,
UDP-GICNAC
AND
UDP-GALNAC
ON
A
MULTI-GRAM
SCALE
......................................................................
-
31
-
2.1
ABSTRACT
............................................................................................................
-32-
2.2
INTRODUCTION
.......................................................................................................
-32-
2.3 RESULTS
AND
DISCUSSION
....................................................................................
-
35
-
2.3.1
MP-CE
BASED
STY
OPTIMIZATION
OF
THE
NOVEL
ENZYME
MODULE
(EM
UDP-HEXNAC)
.................................................................................................
-
35
-
2.3.2
A
NOVEL
REPETITIVE
BATCH
WORKFLOW
FOR
AN
EFFICIENT
NUCLEOTIDE
SUGAR
PRODUCTION
........................................................................................................
-
36
-
2.3.3
SUBSTRATE
AND
PRODUCT
ACCUMULATION
DURING
THE
SYNTHESIS
WORKFLOW
............
-
38
-
2.3.4
EFFECTIVE
SYNTHESIS
OF
NUCLEOTIDE
SUGARS
IN
AN
APPLICATION-BASED
WORKFLOW
...........................................................................................................
-
39
-
2.3.5
CRITICAL
COMPARISON
WITH
CHEMICAL
SYNTHESIS
STRATEGIES
................................
-
47
-
2.4
CONCLUSION
......................................................................................................
-
48
-
2.5
MATERIALS
AND
METHODS
...................................................................................
-
49
-
2.5.1
RECOMBINANT
ENZYME
PRODUCTION
AND
PURIFICATION
........................................
-
49
-
2.5.2
MULTIPLEXED
CAPILLARY
ELECTROPHORESIS
(MP-CE)
WITH
UV-VIS
DETECTION
........
-
50
-
2.5.3
ACTIVITY
ASSAY
FOR
RECOMBINANT
KINASES
AND
PYROPHOSPHORYLASES
................
-
50
-
2.5.4
REPETITIVE
BATCH
SYNTHESIS
OF
UDP-GAL
(20
ML
SCALE)
..................................
-
51
-
2.5.5
REPETITIVE
BATCH
SYNTHESIS
OF
UDP-GICNAC
AND
UDP-GALNAC
(20
ML
SCALE)
...............................................................................................................
-
51
-
2.5.6
REPETITIVE
BATCH
SYNTHESIS
OF
UDP-GALNAC
(200
ML
SCALE)
........................
-
52
-
2.5.7
ESI-MS
PRODUCT
VERIFICATION
............................................................................
-
52
-
2.5.8
AVERAGE
YIELD
CALCULATION
...............................................................................
-
52
-
2.6
CONTRIBUTIONS
...................................................................................................
-
52
-
2.7
REFERENCES
.....................................................................................................
-
53
-
CHAPTER
3:
ENZYMATIC
SYNTHESIS
OF
N-ACETYILACTOSAMINE
(LACNAC)
TYPE
1
OLIGOMERS
AND
CHARACTERIZATION
AS
MULTIVALENT
GALECTIN
LIGANDS
............
-
57
-
3.1
ABSTRACT
............................................................................................................
-58-
3.2
INTRODUCTION
.......................................................................................................
-58-
3.3
RESULTS
AND
DISCUSSION
....................................................................................
-
60
-
3.3.1
NOVEL
ENZYME
MODULE
P3GALT
(EM
|33GALT)
FOR
AN
EFFICIENT
GLYCAN
TAILORING
.............................................................................................................
-
60
-
3.3.2
TAILORING
NEO-
GLYCOPROTEINS
.............................................................................
-
65
-
3.3.3
GALECTIN
BINDING
STUDIES
USING
THE
NOVEL
NEO-
GLYCOPROTEINS
.........................
-
68
-
3.4
CONCLUSION
........................................................................................................
-70-
3.5
MATERIALS
AND
METHODS
.....................................................................................
-
70
-
3.5.1
ENZYMATIC
SYNTHESIS
OF
UDP-GAL
AND
UDP-GICNAC
AND
THEIR ANALYSIS
.........
-
70
-
3.5.2
CLONING
OF
A
NOVEL
DESIGNED
P3-GALT
FUSION
CONSTRUCT
.................................
-
71
-
3.5.3
PREPARING
HUMAN
GALECTINS
AND
RECOMBINANT
ENZYMES
................................
-
71
-
3.5.4
CONDITIONS
OF
THE
ENZYME
ACTIVITY
ASSAYS
.......................................................
-
72
-
3.5.5
POLY-
LACNAC
TYPE
1
OLIGOMER
SYNTHESIS
IN
A
ONE-POT
APPROACH
...................
-
73
-
3.5.6
POLY-
LACNAC
TYPE
1
OLIGOMER
TAILORING
IN
A
SEQUENTIAL
MODE
........................
-
73
-
3.5.7
HPLC
AND
ESI-MS
ANALYSIS
............................................................................
-74
-
3.5.8
TAILORING
NOVEL
NEO-GLYCOPROTEINS
....................................................................
-
74
-
3.5.9
BINDING
ASSAYS
AND
STATISTICAL
EVALUATION
FOR
GAL-3
AND
GAL-3A
...................
-
75
-
3.6
CONTRIBUTIONS
.....................................................................................................
-
76
-
3.7
REFERENCES
.......................................................................................................
-
76
-
CHAPTER
4:
ENZYMATIC
CASCADE
SYNTHESIS
PROVIDES
NOVEL
LINEAR
HUMAN
MILK
OLIGOSACCHARIDES
AS
REFERENCE
STANDARDS
FOR
XCGE-LIF
BASED
HIGH-THROUGHPUT
ANALYSIS
.......................................................
-
81
-
4.1
ABSTRACT
............................................................................................................
-82-
4.2
INTRODUCTION
.......................................................................................................
-
82
-
4.3
RESULTS
AND
DISCUSSION
....................................................................................
-
84
-
4.3.1
SEMI-SEQUENTIAL
ONE-POT
SYNTHESIS
OF
LONG-CHAINED
HMOS
LIKE
OLIGOMERS
..........................................................................................................
-
84
-
4.3.2
EVALUATION
OF
NOVEL
OLIGOMERIC
STRUCTURES
.......................................................
-
86
-
4.3.3
DETECTING
LOW
ABUNDANT
OLIGOSACCHARIDES
OF
LARGER
CHAIN
LENGTH
.................
-
88
-
4.3.4
CRITICAL
RESULT
VALUATION
WITH
THE
LITERATURE
STATE
FOR
ALTERNATIVE
SYNTHETIC
ROUTES
................................................................................................................
-
90
-
4.4
CONCLUSION
........................................................................................................
-91-
4.5
MATERIALS
AND
METHODS
.....................................................................................
-
92
-
4.5.1
PREPARING
RECOMBINANT
ENZYMES
.....................................................................
-
92
-
4.5.2
CE-LIF
METHOD
.......................................................................
-92-
VI
4.5.3
ENZYME
ACTIVITY
ASSAY
USING
UNMODIFIED
SUBSTRATES
......................................
-
92
-
4.5.4
CE-LIF
SAMPLE
PREPARATION
...........................................................................
-
92
-
4.5.5
GICNAC
TERMINATED
LNNT
OLIGOMER
SYNTHESIS
(UNEVEN)
................................
-
93
-
4.5.6
P4GAL
TERMINATED
LNNT
OLIGOMER
SYNTHESIS
(EVEN)
......................................
-
93
-
4.5.7
P3GAL
TERMINATED
LNT
OLIGOMER
SYNTHESIS
(EVEN)
........................................
-
93
-
4.5.8
XCGE-LIF
METHOD
...........................................................................................
-
94
-
4.5.9
SPECIFIC
EXOGLYCOSIDASE
DIGEST
.......................................................................
-
94
-
4.5.10
IN-DEPTH
SAMPLE
CLEAN-UP
BY
COTTON
HILIC-SPE
............................................
-
95
-
4.5.11
MASS
SPECTROMETRY
(MALDI-TOF)
..................................................................
-
95
-
4.5.12
HPLC-ELDS/UV/ESI-MS
................................................................................
-
95
-
4.6
CONTRIBUTIONS
...................................................................................................
-
96
-
4.7
REFERENCES
......................................................................................................
-
96
-
CHAPTER
5:
NOVEL
ENZYMATIC
CASCADES
FOR
TAILORED
13
C
6
AND
15
N
ENRICHED
HUMAN
MILK
OLIGOSACCHARIDES
..............................................
-103
-
5.1
ABSTRACT
..........................................................................................................
-104-
5.2
INTRODUCTION
....................................................................................................
-104-
5.3
RESULTS
AND
DISCUSSION
.................................................................................
-107
-
5.3.1
REPETITIVE
BATCH
SYNTHESIS
OF
ISOTOPIC-LABELLED
NUCLEOTIDE
SUGARS
..............
-107
-
5.3.2
SEQUENTIAL
SYNTHESIS
OF
13
C
6
LABELLED
HMOS
...............................................
-108
-
5.3.3
MS-BASED
ABSOLUTE
COMPOUND
QUANTIFICATION
IN
MILK
..................................
-113
-
5.4
CONCLUSION
.....................................................................................................
-118-
5.5
MATERIALS
AND
METHODS
..................................................................................
-119
-
5.5.1
PRODUCTION
AND
PURIFICATION
OF
RECOMBINANT
ENZYMES
.................................
-119-
5.5.2
ACTIVITY
ASSAY
FOR
THE
RECOMBINANT
ENZYMES
................................................
-119-
5.5.3
CE-LIF
AND
XCGE-LIF
METHODS
FOR
HMOS
ANALYSIS
....................................
-119
-
5.5.4
REPETITIVE
BATCH
BASED
ENZYMATIC
NUCLEOTIDE
SUGAR
SYNTHESIS
...................
-119
-
5.5.5
SEQUENTIAL
SYNTHESIS
OF
NATIVE
AND
13
C
6
ENRICHED
HMOS
............................
-120
-
5.5.6
ENZYMATIC
TAILORING
OF
[
13
C6/
15
N]LACTO-/V-NEO-TETRAOSE
................................
-120
-
5.5.7
TOC
BASED
PURITY
EVALUATION
OF
THE
TAILORED
[
13
C6/
15
N]LACTO-/V-NEO-
TETRAOSE
...........................................................................................................
-121
-
5.5.8
MASS
SPECTROMETRY-BASED
PRODUCT
EVALUATION
.............................................
-121
-
5.5.9
ESI-MS
ANALYSIS
OF
THE
NUCLEOTIDE
SUGARS
AND
HMOS
................................
-122
-
5.5.10
OLIGOSACCHARIDE
EXTRACTION
FROM
MILK
AS
A
COMPLEX
SAMPLE
MATRIX
............
-122
-
5.5.11
MALDI-TOF-MS
BASED
ABSOLUTE
QUANTIFICATION
APPROACH
...........................
-123
-
5.6
CONTRIBUTIONS
..................................................................................................
-123
-
5.7
REFERENCES
....................................................................................................
-124-
CHAPTER
6:
CONCLUDING
REMARKS
AND
OUTLOOK
.............................................................
-131
-
VII
6.1
REFERENCES
....................................................................................................
-135
-
CHAPTER
7:
SUPPORTING
INFORMATION
FOR
CHAPTER
2
......................................................
-140
-
7.1
ENZYME
CASCADE
PARAMETER
SCREENING
(M.
SC.
CHRISTIAN
ZERHUSEN
AND
DR.
RER
NAT.
CLAUDIA
WAHL)
.............................................................................
-141
-
7.1.1
KINETIC
DATA
OF
AGX1
......................................................................................
-141
-
7.1.2
SCREENING
FOR
OPTIMIZED
METAL
ION
RATIOS
(EM-UDP-HEXNAC)
....................
-142
-
7.1.3
SCREENING
FOR
OPTIMIZED
ENZYME
RATIOS
(AGX1
:PP,ASE)
..............................
-143
-
7.1.4
EM
UDP-HEXNAC
SYNTHESIS
SCALE-UP
FOR
UDP-GALNAC
..............................
-143
-
7.2 MASS
SPECTROMETRY
(ESI-MS)
........................................................................
-144
-
7.3
REPETITIVE
BATCH
WORKFLOW
SCALE-UP
(200
ML)
..............................................
-146
-
CHAPTER
8:
SUPPORTING
INFORMATION
FOR
CHAPTER
3
......................................................
-148
-
8.1
NOVEL
P3GALT
CONSTRUCT
DESIGN
....................................................................
-149
-
8.2
BIOCHEMICAL
CHARACTERIZATION
FOR
A
NOVEL
P3GALT
CONSTRUCT
(M.
SC.
CARINA
DEY)
....................................................................................................
-150
-
8.3
ENZYME
MODULES
(EM
P4GALT
AND
EM
P3GLCNACT)
..................................
-152-
8.4
NUCLEOTIDE
SUGAR
QUANTIFICATION
ON
A
SINGLE
CAPILLARY
CE-UV
.....................
-153
-
8.5 GLYCAN
SYNTHESIS
ANALYZED
BY
RP-HPLC-UV
(DR.
RER
NAT
DOMINIC
LAAF)....
-156
-
8.6 ISOLATION
OF
SQUARATE
MONOAMIDE
ESTERS
IN
A
PREPARATIVE
SCALE
VIA
HPLC
(DR.
RER
NAT
DOMINIC
LAAF)
..................................................................
-160
-
8.7
GALECTIN
3
AND
GALECTIN
3A
BINDING
ASSAYS
(DR.
RER
NAT
DOMINIC
LAAF)
.....
-162
-
6.8
ESI-MS
COMPOUND
ANALYSIS
..........................................................................
-163
-
8.9
REFERENCE
DATA
FOR
THE
P3GALT
CONSTRUCT
EVALUATION
(M.SC.
CARINA
DEY)
..
-168
-
8.10
SUPPORTING
REFERENCES:
................................................................................
-170
-
CHAPTER
9:
SUPPORTING
INFORMATION
FOR
CHAPTER
4
......................................................
-171
-
9.1
MALDI-TOF-MS
PRODUCT
ANALYSIS
................................................................
-172
-
9.2
SPECIFIC
DIGEST
OF
THE
SYNTHESIZED
HMOS
.....................................................
-175
-
9.3
HPLC-ELDS/UV/ESI-MS
...............................................................................
-
178
-
CHAPTER
10:
SUPPORTING
INFORMATION
FOR
CHAPTER
5
......................................................
-182
-
10.1
REPETITIVE
BATCH
SYNTHESIS
OF
ISOTOPIC
NUCLEOTIDE
SUGARS
............................
-183
-
10.2
CE-UV
ANALYSIS
-
NUCLEOTIDE
SUGAR
SYNTHESIS
..............................................
-184
-
10.3
CE-LIF
ANALYSIS
.............................................................................................
-185-
10.4
ESI-MS
COMPOUND
ANALYSIS
..........................................................................
-191
-
10.5
MALDI-TOF-MS
COMPOUND
ANALYSIS
............................................................
-
200
-
10.6
PURITY
EVALUATION
OF
COMPOUND
25
VIA
TOC
ANALYTIC
....................................
-
204
-
10.7
RAPID
ABSOLUTE
QUANTIFICATION
OF
(MILK
OS)
TETRAOSE
IN
COMPLEX
(MILK)
MATRIX
SAMPLES
...............................................................................................
-
206
-
CHAPTER
11:
APPENDIX
.......................................................................................................
-
208
-
VIII
11.1
LIST
OF
EQUIPMENT
...........................................................................................
-
208
-
11.2
LIST
OF
SOFTWARE
..............................................................................................
-
209
-
11.3
LIST
OF
FIGURES
.................................................................................................
-
210
-
11.4
LIST
OF
SCHEMES
..............................................................................................
-210-
11.5
LIST
OF
TABLES
..................................................................................................
-211
-
11.6
LIST
OF
EQUATIONS
.............................................................................................
-211-
11.7
LIST
OF
SUPPORTING
FIGURES
.............................................................................
-211-
11.8
LIST
OF
SUPPORTING
TABLES
...............................................................................
-213-
11.9
LIST
OF
SUPPORTING
SCHEMES
..........................................................................
-213-
11.10
REPRINT
PERMISSION
.........................................................................................
-213-
11.11
EIDESSTATTLICHE
ERKLARUNG
...............................................................................
-
214
-
IX
|
| any_adam_object | 1 |
| author | Fischöder, Thomas |
| author_GND | (DE-588)1202357113 |
| author_facet | Fischöder, Thomas |
| author_role | aut |
| author_sort | Fischöder, Thomas |
| author_variant | t f tf |
| building | Verbundindex |
| bvnumber | BV046869911 |
| ctrlnum | (OCoLC)1157256371 (DE-599)DNB1207482595 |
| discipline | Chemie / Pharmazie Biologie |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV046869911 |
| illustrated | Illustrated |
| indexdate | 2024-12-24T08:18:25Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-032280072 |
| oclc_num | 1157256371 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-83 |
| owner_facet | DE-355 DE-BY-UBR DE-83 |
| physical | XIV, 215 Seiten Illustrationen, Diagramme 21 cm |
| publishDate | 2019 |
| publishDateSearch | 2019 |
| publishDateSort | 2019 |
| record_format | marc |
| spellingShingle | Fischöder, Thomas Modularisation of novel multi-enzyme cascades and synthesis strategy development |
| subject_GND | (DE-588)4113937-9 |
| title | Modularisation of novel multi-enzyme cascades and synthesis strategy development |
| title_auth | Modularisation of novel multi-enzyme cascades and synthesis strategy development |
| title_exact_search | Modularisation of novel multi-enzyme cascades and synthesis strategy development |
| title_full | Modularisation of novel multi-enzyme cascades and synthesis strategy development vorgelegt von Thomas Fischöder (M. Sc.) Biotechnologie |
| title_fullStr | Modularisation of novel multi-enzyme cascades and synthesis strategy development vorgelegt von Thomas Fischöder (M. Sc.) Biotechnologie |
| title_full_unstemmed | Modularisation of novel multi-enzyme cascades and synthesis strategy development vorgelegt von Thomas Fischöder (M. Sc.) Biotechnologie |
| title_short | Modularisation of novel multi-enzyme cascades and synthesis strategy development |
| title_sort | modularisation of novel multi enzyme cascades and synthesis strategy development |
| topic_facet | Hochschulschrift |
| url | https://d-nb.info/1207482595/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032280072&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT fischoderthomas modularisationofnovelmultienzymecascadesandsynthesisstrategydevelopment |