Selective modifications of the antibiotic moenomycin A: new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
2001
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Leipzig, Univ., Diss., 2001 |
| Beschreibung: | 167 Bl. graph. Darst. : 30 cm |
Internformat
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| 245 | 1 | 0 | |a Selective modifications of the antibiotic moenomycin A |b new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A |c vorgelegt von Andrij Buchynskyy |
| 246 | 1 | 1 | |a Selektive Modifizierungen des Antibiotikums Moenomycin A |
| 264 | 1 | |c 2001 | |
| 300 | |a 167 Bl. |b graph. Darst. : 30 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
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Datensatz im Suchindex
| _version_ | 1812460652400214016 |
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| adam_text |
CONTENTS
PAGE
1 INTRODUCTION. 1
1.1 PEPTIDOGLYCAN BIOTHYNSESIS AS A TARGET FOR ANTIBIOTICS. 1
1.2 INHIBITION OF EXTRACELLULAR STEPS OF PEPTIDOGLYCAN BIOTHYNTHESIS. 2
2 AIM OF THE WORK. 7
3 PREVIOUS WORK. 8
4 RESULTS AND DISCUSSION. 10
4.1 INTRODUCTION OF AN ALIPHATIC AMINO GROUP INTO MOENOMYCIN A
VIA
THE DIAZONIUM SALT ROUTE. 10
4.1.1 SYNTHESIS OF THE HETEROBIFUNCTIONAL REAGENT 2. 10
4.1.2 REACTION OF MOENOMYCIN A WITH THE DIAZONIUM SALT OBTAINED FROM 2.
10
4.2 SELECTIVE REACTION OF MOENOMYCIN-NH
2
(5) WITH ISOTHIOCYANATES. 13
4.2.1 SYNTHESIS OF COUMARIN ISOTHIOCYANATE (9). 13
4.2.2 SYNTHESIS OF 6-AMINOTETRAMETHYLRHODAMINE (13). 15
4.2.3 OTHER FLUORESCENCE LABELS USED FOR COUPLING TO 5. 17
4.2.4 SELECTIVE ATTACHING OF FLUORESCENT LABELS TO MOENOMYCIN-NH
2. 17
4.3 SELECTIVE ACYLATION OF AN AMINO GROUP OF 5 BY A N-HYDROXYSUCCINIMIDE
ACTIVATED CARBOXYLIC ACID. 20
4.3.1 COMPOUND 19 AS THE MODEL ACYLATION REAGENT. 20
4.3.2 ACYLATION OF THE AMINO GROUP OF 5 WITH 19. 21
4.3.3 PREPARATION OF MODEL COMPOUND 21. 22
4.3.4 FORMATION OF 20 BY REACTION OF 3 WITH THE DIAZONIUM SALT DERIVED
FROM 21. 22
4.4 SELECTIVE REACTION OF MOENOMYCIN-NH
2
WITH SQUARIC ACID DERIVATIVES. 23
4.4.1 SELECTIVE REACTION OF 5 WITH SQUARIC ACID DIETHYL ESTER (22). 23
4.4.2 COUPLING OF FLUORESCENT LABELS TO MOENOMYCIN USING THE SQUARIC
ACID LINKER. 25
4.4.3 FIRST ATTEMPTS ON THE SYNTHESIS OF MOENOMYCIN-AMPICILLIN CONJUGATE
33. 29
4.4.4 PREPARATION OF BSA-MOENOMYCIN CONJUGATES USING A SQUARIC ACID
LINKER. 31
4.5
IN-VIVO ANTIBIOTIC ACTIVITY OF 5 AND ITS DERIVATIVES. 34
4.6 APPLICATIONS OF THE PREPARED MOENOMYCIN DERIVATIVES IN
BIOCHEMICAL AND BIOPHYSICAL INVESTIGATIONS. 36
4.6.1 AFFINITY CHROMATOGRAPHY. 36
4.6.2 PHOTOAFFMITY LABELING. 37
BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/963437917
4.6.3 SPR (SURFACE PLASMON RESONANCE, BIACORE). 38
4.6.4 MEMBRANE ANCHORING AND INTERVESICLE TRANSFER EXPERIMENTS, FRET
(FLUORESCENCE RESONANCE ENERGY TRANSFER). 40
4.6.5 FCS (FLUORESCENCE CORRELATION SPECTROSCOPY). 41
4.6.6 IMMUNOLOGICAL EXPERIMENTS TO RAISE ANTI-MOENOMYCIN ANTIBODIES. 41
4.7 A NEW APPROACH FOR THE INTRODUCTION OF AN ORTHOGONAL AMINO
GROUP INTO MOENOMYCIN A. 42
4.7.1 SYNTHESIS OF 2-[(E)-3-(4-METHOXYPHENYL)-2-BUTENYL]THIOURONIUM
ACETATE (37). 42
4.7.2 REACTION OF THIOURONIUM ACETATE
40 WITH MODEL COMPOUNDS 41 AND 42. 43
4.7.3 REACTION OF MOENOMYCIN A WITH
40. 44
4.7.4 WHAT ARE THE STRUCTURAL REQUIREMENTS OF THE THIOURONIUM SALTS TO
REACT WITH
MOENOMYCIN A?. 45
4.7.5 METHOD FOR THE SYNTHESIS OF THE NEW AMINO-MOENOMYCIN DERIVATIVE.
50
4.7.6 ANTIBIOTIC ACTIVITY OF THE MOENOMYCIN DERIVATIVES PREPARED
VIA THE
THIOURONIUM SALT ROUTE. 57
4.8 SELECTIVE REMOVAL OF THE LIPID PART FROM MOENOMYCIN A. 58
4.8.1 CLEAVAGE OF THE LIPID PART FROM MOENOMYCIN A. 58
4.8.2 INTRODUCTION OF ALIPHATIC AMINO GROUP INTO DELIPIDO-MOENOMYCIN 70.
60
5 OUTLOOK. 63
6 SUMMARY. 64
7 ZUSAMMENFASSUNG (SUMMARY IN GERMAN LANGUAGE). 66
8 EXPERIMENTAL PART. 68
8.1 GENERAL. 68
8.2 SYNTHESIS OF MOENOMYCIN-NIL (5). 72
8.2.1 PREPARATION OF DIAMINE
2. 72
8.2.2 REACTION OF DIAZONIUM SALT OBTAINED FROM 2 WITH MOENOMYCIN A. 73
8.3 PREPERATION OF FLUORESCENT ISOTHIOCYANATES. 75
8.3.1 SYNTHESIS OF COUMARIN ISOTHIOCYANATE 9. 75
8.3.2 SYNTHESIS OF AMINO-TETRAMETHYLRHODAMINE
14. 78
8.4 SELECTIVE ATTACHING OF FLUORESCENT ISOTHIOCYANATES TO MOENOMYCIN-NH
2 (5). 83
8.4.1 COUPLING OF COUMARIN ISOTHIOCYANATE 9 TO 5. 83
8.4.2 COUPLING OF TETRAMETHYLRHODAMINE ISOTHIOCYANATE TO 5. 85
8.4.3 COUPLING OF FLUORESCEIN ISOTHIOCYANATE TO 5. 87
8.4.4 COUPLING OF SITS TO 5. 88
8.5 SELECTIVE REACTION OF 5 WITH NHS-DERIVATIVE OF CARBOXYLIC ACID. 90
8.5.1 PREPARATION OF PHENYLACETIC ACID 2,5-DIOXO PYRROLIDIN-L-YL ESTER
(19). 90
8.5.2 FORMATION OF
21 FROM 2 AND 19. 91
8.5.3 SYNTHESIS OF COMPOUND 20 BY SELECTIVE REACTION OF 5 WITH 19. 92
8.5.4 SYNTHESIS OF 20 BY REACTION OF 3 WITH DIAZONOUM SALT DERIVED FROM
21. 93
8.6 SELECTIVE REACTION OF AMINE 5 WITH SQUARIC ACID DERIVATIVES. 95
8.6.1 REACTION OF 5 WITH SQUARIC ACID DIETHYL ESTER 22. 95
8.6.2 REACTION OF 5 WITH SQUARIC ACID AMIDE ESTERS OF FLUORESCENT
LABELS. 97
8.6.3 SYNTHESIS OF MOENOMYCIN-AMPICILLIN CONJUGATE 33. 107
8.6.4 COUPLING OF
23 TO SOLID SUPPORT (LYSINE-SEPHAROSE 4B). 111
8.6.5 PREPARATION OF BSA-MOENOMYCIN CONJUGATES
37. 112
8.7 NEW METHOD FOR SELECTIVE MODIFICATION OF MOENOMYCIN A
VIA THIOURONIUM
SALTS. 116
8.7.1 REACTION OF THIOURONIUM ACETATE 40 WITH MODEL COMPOUNDS AND
MOENOMYCIN A 116
8.7.2 SYNTHESIS OF OTHERS THIOURONIUM SALTS AND THEIR REACTION WITH
MOENOMYCIN A. 122
8.7.3 SYNTHESIS OF THIOURONIUM BROMIDE
48. 126
8.7.4 TREATMENT OF THIOURONIUM BROMIDE
48 WITH MOENOMYCIN A. 129
8.7.5 PREPARATION OF THIOURONIUM SALT
50. 131
8.7.6 TREATMENT OF 50 WITH MOENOMYCIN A. 132
8.7.7 SYNTHESIS OF AMINO-THIOURONIUM SALT
64. 134
8.7.8 REACTION OF MOENOMYCIN A WITH THIOURONIUM SALT
63. 140
8.7.9 REACTION OF MOENOMYCIN A WITH THIOURONIUM SALT 64. 144
8.7.10 PREPARATION OF A NEW MOENOMYCIN-RHODAMINE 6G DERIVATIVE 69. 149
8.8 SYNTHESIS OF DELIPIDO-MOENOMYCIN DERIVATIVES 70 AND 74. 151
8.8.1 HYDROLYTIC CLEAVAGE OF THE LIPID PART IN MOENOMYCIN A. 151
8.8.2 REACTION OF 70 WITH DIAZONIUM SALT. 154
8.8.3 PREPARATION OF
74 FROM 70 AND THIOURONIUM SALT 64. 155
8.8.4 LIPID PRODUCTS BY REMOVING OF THE LIPID PART FROM MOENOMYCIN A.
157
9 ABBREVIATION. 160
10 REFERENCES. 162 |
| any_adam_object | 1 |
| author | Buchynskyy, Andrij 1973- |
| author_GND | (DE-588)123430488 |
| author_facet | Buchynskyy, Andrij 1973- |
| author_role | aut |
| author_sort | Buchynskyy, Andrij 1973- |
| author_variant | a b ab |
| building | Verbundindex |
| bvnumber | BV014132377 |
| ctrlnum | (OCoLC)634119354 (DE-599)BVBBV014132377 |
| format | Book |
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| id | DE-604.BV014132377 |
| illustrated | Illustrated |
| indexdate | 2024-10-09T18:06:12Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009684947 |
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| owner_facet | DE-91 DE-BY-TUM DE-355 DE-BY-UBR |
| physical | 167 Bl. graph. Darst. : 30 cm |
| publishDate | 2001 |
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| publishDateSort | 2001 |
| record_format | marc |
| spelling | Buchynskyy, Andrij 1973- Verfasser (DE-588)123430488 aut Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A vorgelegt von Andrij Buchynskyy Selektive Modifizierungen des Antibiotikums Moenomycin A 2001 167 Bl. graph. Darst. : 30 cm txt rdacontent n rdamedia nc rdacarrier Leipzig, Univ., Diss., 2001 Aromatische Verbindungen (DE-588)4129374-5 gnd rswk-swf Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Murein (DE-588)4126234-7 gnd rswk-swf Diazoniumverbindungen (DE-588)4192798-9 gnd rswk-swf Moenomycin A (DE-588)4272680-3 gnd rswk-swf Modifizierung (DE-588)4299539-5 gnd rswk-swf Moenomycinderivate (DE-588)4422043-1 gnd rswk-swf Aminogruppe (DE-588)4326843-2 gnd rswk-swf Regioselektivität (DE-588)4307782-1 gnd rswk-swf Biosynthese (DE-588)4006902-3 gnd rswk-swf Chemische Reaktion (DE-588)4009853-9 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Moenomycin A (DE-588)4272680-3 s Modifizierung (DE-588)4299539-5 s Chemische Reaktion (DE-588)4009853-9 s Diazoniumverbindungen (DE-588)4192798-9 s Aromatische Verbindungen (DE-588)4129374-5 s DE-604 Moenomycinderivate (DE-588)4422043-1 s Aminogruppe (DE-588)4326843-2 s Regioselektivität (DE-588)4307782-1 s Murein (DE-588)4126234-7 s Biosynthese (DE-588)4006902-3 s Reaktionsmechanismus (DE-588)4177123-0 s DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009684947&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Buchynskyy, Andrij 1973- Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A Aromatische Verbindungen (DE-588)4129374-5 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Murein (DE-588)4126234-7 gnd Diazoniumverbindungen (DE-588)4192798-9 gnd Moenomycin A (DE-588)4272680-3 gnd Modifizierung (DE-588)4299539-5 gnd Moenomycinderivate (DE-588)4422043-1 gnd Aminogruppe (DE-588)4326843-2 gnd Regioselektivität (DE-588)4307782-1 gnd Biosynthese (DE-588)4006902-3 gnd Chemische Reaktion (DE-588)4009853-9 gnd |
| subject_GND | (DE-588)4129374-5 (DE-588)4177123-0 (DE-588)4126234-7 (DE-588)4192798-9 (DE-588)4272680-3 (DE-588)4299539-5 (DE-588)4422043-1 (DE-588)4326843-2 (DE-588)4307782-1 (DE-588)4006902-3 (DE-588)4009853-9 (DE-588)4113937-9 |
| title | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A |
| title_alt | Selektive Modifizierungen des Antibiotikums Moenomycin A |
| title_auth | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A |
| title_exact_search | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A |
| title_full | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A vorgelegt von Andrij Buchynskyy |
| title_fullStr | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A vorgelegt von Andrij Buchynskyy |
| title_full_unstemmed | Selective modifications of the antibiotic moenomycin A new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A vorgelegt von Andrij Buchynskyy |
| title_short | Selective modifications of the antibiotic moenomycin A |
| title_sort | selective modifications of the antibiotic moenomycin a new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis selektive modifizierungen des antibiotikums moenomycin a |
| title_sub | new tools for the investigation of the transglycosylation step of peptidoglycan biosynthesis = Selektive Modifizierungen des Antibiotikums Moenomycin A |
| topic | Aromatische Verbindungen (DE-588)4129374-5 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Murein (DE-588)4126234-7 gnd Diazoniumverbindungen (DE-588)4192798-9 gnd Moenomycin A (DE-588)4272680-3 gnd Modifizierung (DE-588)4299539-5 gnd Moenomycinderivate (DE-588)4422043-1 gnd Aminogruppe (DE-588)4326843-2 gnd Regioselektivität (DE-588)4307782-1 gnd Biosynthese (DE-588)4006902-3 gnd Chemische Reaktion (DE-588)4009853-9 gnd |
| topic_facet | Aromatische Verbindungen Reaktionsmechanismus Murein Diazoniumverbindungen Moenomycin A Modifizierung Moenomycinderivate Aminogruppe Regioselektivität Biosynthese Chemische Reaktion Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009684947&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT buchynskyyandrij selectivemodificationsoftheantibioticmoenomycinanewtoolsfortheinvestigationofthetransglycosylationstepofpeptidoglycanbiosynthesisselektivemodifizierungendesantibiotikumsmoenomycina AT buchynskyyandrij selektivemodifizierungendesantibiotikumsmoenomycina |