Carbohydrate mimics concepts and methods
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1998
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| 245 | 1 | 0 | |a Carbohydrate mimics |b concepts and methods |c ed. by Yves Chapleur |
| 264 | 1 | |a Weinheim [u.a.] |b Wiley-VCH |c 1998 | |
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| 650 | 7 | |a Glucides - Synthèse |2 ram | |
| 650 | 7 | |a Glucides |2 ram | |
| 650 | 4 | |a Carbohydrates |v Congresses | |
| 650 | 4 | |a Carbohydrates |x Synthesis |v Congresses | |
| 650 | 4 | |a Carbohydrates |x chemical synthesis |v Congresses | |
| 650 | 4 | |a Carbohydrates |x chemistry |v Congresses | |
| 650 | 4 | |a Mimicry (Chemistry) |v Congresses | |
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| adam_text | CARBOHYDRATE MIMICS CONCEPTS AND METHODS EDITED BY YVES CHAPLEUR WITH
COLLABORATION OF HANS-JOSEF ALTENBACH, FRANCOISE CHRETIEN, JOSE MARCO
CONTELLES, FRANCESCO NICOTRA, AMELIA P. RAUTER AND STANLEY M. ROBERTS
WILEY-VCH WEINHEIM * BERLIN * NEW YORK * CHICHESTER * TORONTO * BRISBANE
* SINGAPORE CONTENTS FOREWORD V LIST OF CONTRIBUTORS XIX 1 RECENT
ADVANCES IN THE SYNTHESIS OF CYCLIC POLYETHER MARINE NATURAL PRODUCTS 1
K. C. NICOLAOU, M. H. D. POSTEMA AND N. D. MILLER 1.1 INTRODUCTION 1 1.2
SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF CYCLIC ETHERS 3 1.3 TOTAL
SYNTHESIS OF BREVETOXIN B 3 1.4 RECENT DEVELOPMENTS IN POLYETHER
SYNTHESIS 4 1.4.1 RADICAL-BASED REDUCTION OF THIONOLACTONES TO CYCLIC
ETHERS 4 1.4.2 SYNTHESIS OF L,L -BISTETRAHYDROPYRAN SYSTEMS VIA
COPPER(I)- PROMOTED STILLE COUPLING 7 1.4.3 THE OLEFIN METATHESIS
APPROACH TO CYCLIC ENOL ETHER CONSTRUCTION 11 1.5 CONCLUSION 14 1.6
REFERENCES 15 2 STEREOSELECTIVE SYNTHESIS OF C-DISACCHARIDES, AZA-C-
DISACCHARIDES AND C-GLYCOSIDES OF CARBAPYRANOSES USING THE NAKED
SUGARS 19 P. VOGEL, R. FERRITTO, K. KRAEHENBUEHL AND A. BAUDAT 2.1
INTRODUCTION 19 2.2 SYNTHETIC METHODS 20 2.3 THE NAKED SUGAR APPROACH
29 2.3 C-GLYCOSIDES OF CARBAPYRANOSES AND ANALOGUES 35 2.4
BRANCHED-CHAIN CARBOHYDRATES THROUGH CROSS-ALDOLISATIONS 38 2.5
SYNTHESIS OF AN AZA-C(L* 3)-DISACCHARIDE 40 2.6 CONCLUSION 42 2.7
REFERENCES 42 XVIII 3 THE NITRILE OXIDE/ISOXAZOLINE ROUTE TO
C-DISACCHARIDES 49 R. M. PATON 3.1 INTRODUCTION . 49 3.2 GENERATION OF
NITRILE OXIDES 51 3.3 (L- 2)- AND (L- 3)-CARBONYL-LINKED DISACCHARIDES
52 3.4 (1 * 6)-HYDROXYMETHY LENE-LINKED DISACCHARIDES 56 3.5
HIGHER-CARBON DIALDOSES 60 3.6 CONCLUSION 63 3.7 REFERENCES 64 4
SYNTHESIS OF GLYCOSYL PHOSPHATE MIMICS 67 F. NICOTRA 4.1 INTRODUCTION 67
4.2 ROLES OF GLYCOSYL PHOSPHATES 67 4.3 MIMICS OF NATURAL PHOSPHATES 68
4.4 MIMICS OF GLYCOSYL PHOSPHATES 69 4.4.1 DIRECT METHODS OF GLYCOSYL
METHYLPHOSPHONATE SYNTHESIS 70 4.4.2 INDIRECT METHODS OF GLYCOSYL
METHYLPHOSPHONATE SYNTHESIS 72 4.4.2.1 SYNTHESIS OF C-GLYCOSYL HALIDES
73 4.4.2.2 CONVERSION OF C-GLYCOSYL HALIDES INTO PHOSPHONATES 75 4.5
MIMICS OF N-ACETYL-A-D-GLUCOSAMINE 1-PHOSPHATE AND N-
ACETYL-A-D-MANNOSAMINE 1-PHOSPHATE 77 4.5.1 THE BIOLOGICAL ROLES 77
4.5.2 SYNTHESIS 79 4.6 CONCLUSION 83 4.7 REFERENCES 83 5 SYNTHETIC
STUDIES ON GLYCOSIDASE INHIBITORS COMPOSED OF 5A-CARBA-SUGARS 87 S.
OGAWA 5.1 INTRODUCTION 87 5.2 SYNTHESIS OF BIOLOGICALLY ACTIVE NATURAL
COMPOUNDS CONTAINING 5A-CARBA-SUGARS 89 5.2.1 SYNTHESIS OF VALIDAMYCINS
89 5.2.2 SYNTHESIS OF ACARBOSE 90 5.2.3 SYNTHESIS OF SALBOSTATIN 91
5.2.4 STRUCTURE-ACTIVITY RELATIONSHIP OF NATURALLY OCCURRING GLYCOSIDASE
INHIBITORS COMPOSED OF 5A-CARBA-SUGARS 92 5.3 SYNTHESIS OF
CARBA-OLIGOSACCHARIDES OF BIOLOGICAL INTERESTS 94 XIX 5.3.1
5A -CARBA-MALTOSES LINKED BY IMINO, ETHER, AND SULFIDE LINKAGES 94 5.3.2
SEVERAL CARBA-OLIGOSACCHARIDES: CORE-STRUCTURES OF CELL SURFACE GLYCANS
95 5.4 SYNTHESIS OF GLYCOLIPID ANALOGUES CONTAINING 5A-CARBA- SUGARS 97
5.4.1 GLYCOSYLAMIDE ANALOGUES 97 5.4.2 GLYCOSYLCERAMIDE ANALOGUES 98
5.4.3 GLYCOCEREBROSIDASE INHIBITORS 99 5.5 DEVELOPMENT OF NEW-TYPES OF
GLYCOSIDASE INHIBITORS 100 5.5.1 CHEMICAL MODIFICATION OF THE TREHALASE
INHIBITOR TREHAZOLIN 100 5.5.2 DEVELOPMENT OF
5-AMINO-L,2,3,4-CYCLOPENTANETETRAOL DERIVATIVES AS NEW POTENT
GLYCOSIDASE INHIBITORS 102 5.5.3 JV-ALKYL AND IV-PHENYL CYCLIC ISOUREA
DERIVATIVES OF 5- AMINOCYCLOPENTANEPOLYOL DERIVATIVES: NEW TYPES OF
POTENT A-GLUCOSIDASE INHIBITORS 103 5.6 REFERENCES 104 6 THE DITHIANE
ROUTE FROM CARBOHYDRATES TO CARBOCYCLES 107 K. KROHN, G. BORNER AND S.
GRINGARD 6.1 INTRODUCTION 107 6.2 THREE- TO FIVE-MEMBERED CARBOCYCLIC
RINGS FROM 2-DEOXY RIBOSE 109 6.2.1 FIVE-MEMBERED RING 109 6.2.2
THREE-MEMBERED RINGS 109 6.2.3 FOUR-MEMBERED RING ILL 6. 3 THREE- TO
SEVEN-MEMBERED CARBOCYCLIC RINGS FROM MANNOSE 112 6.3.1 CYCLOPROPANE
DERIVATIVES 112 6.3.2 CYCLOBUTANE DERIVATIVES 113 6.3.3 CYCLOHEXANES AND
CYCLOHEPTANES 114 6.4 APPLICATION TO NATURAL PRODUCT SYNTHESIS 115 6.4.1
VALIDATOL 115 6.4.2 CALCITRIOL 117 6.5 REFERENCES 120 7 NEW REDUCTIVE
CARBOCYCLISATIONS OF CARBOHYDRATE DERIVATIVES PROMOTED BY SAMARIUM
DIIODIDE 123 J. L. CHIARA 7.1 INTRODUCTION 123 XX 7.2 RESULTS AND
DISCUSSION 125 7.2.1 INTRAMOLECULAR C=O/C=O REDUCTIVE COUPLING 125 7.2.2
INTRAMOLECULAR C=O/C=N-OR REDUCTIVE CROSS-COUPLING 131 7.2.3 RING
CONTRACTION OF 6-DEOXY-6-IODO-HEXOPYRANOSIDES 135 7.3 CONCLUSIONS 138
7.4 REFERENCES 139 8 A CONCISE ROUTE TO CARBA-HEXOPYRANOSES AND CARBA-
PENTOFURANOSES FROM SUGAR LACTONES 143 F. CHRETIEN, M. KHALDI AND Y.
CHAPLEUR 8.1 INTRODUCTION 143 8.2 RESULTS 144 8.2.1 CARBAHEXOPYRANOSES
144 8.2.2 CARBAPENTOFURANOSES 152 8.2.3 EPILOGUE 153 8.3 CONCLUSION 154
8.4 REFERENCES 154 9 ASYMMETRIC SYNTHESIS OF AMINOCYCLOPENTITOLS VIA
FREE RADICAL CYCLOISOMERIZATION OF ENANTIOMERICALLY PURE ALKYNE-TETHERED
OXIME ETHERS DERIVED FROM CARBOHYDRATES 157 J. MARCO-CONTELLES 9.1
INTRODUCTION 157 9.2 RESULTS AND DISCUSSION 159 9.2.1 SYNTHESIS AND
RADICAL CYCLIZATION OF D-MANNO DERIVATIVES 6- 8 161 9.2.2 SYNTHESIS AND
RADICAL CYCLIZATION OF D-RIBO DERIVATIVES 16 AND 17 163 9.2.3 SYNTHETIC
ELABORATION OF THE CARBOCYCLIC VINYLTIN DERIVATIVES. SYNTHESIS OF
AMINOCYCLOPENTITOLS 165 9.3 CONCLUSION... 167 9.4 REFERENCES 168 10
CARBOHYDRATES AS SOURCES OF CHIRAL INOSITOL POLYPHOSPHATES AND THEIR
MIMICS 171 D. J. JENKINS, A. M. RILEY AND B. V. L POTTER* 10.1
INTRODUCTION 171 XXI 10.2 SYNTHESIS OF D-2-DEOXY-MYO-INOSITOL
1,3,4,5-TETRAKIS- PHOSPHATE 173 10.2.1 IMPROVED PREPARATION OF METHYL
4,6-0-BENZYLIDENE-A-D- GLUCOPYRANOSIDE AND METHYL
4,6-O-BENZYLIDENE-A-D-MANNO- PYRANOSIDE 176 10.2.2 BENZYLATION OF METHYL
4,6-O-BENZYLIDENE-A-D-GLUCO- PYRANOSIDE AND RELATED REACTIONS 178 10.2.3
PREPARATION OF METHYL 3,4-DI-0-BENZOYL-2-0-BENZYL-6-DEOXY-
A-D-XY/O-HEX-5-ENOPYRANOSIDE 30 180 10.2.4 FERRIER CARBOCYCLISATION OF
30 180 10.2.5 ATTEMPTED INVERSION OF STEREOCHEMISTRY AT POSITION 5 OF 32
181 10.2.6 SYNTHESIS OF D-2-DEOXY-/NYO-INOSITOL 1,3,4,5 TETRAKISPHOS-
PHATE5 183 10.3 SYNTHESIS OF RING-CONTRACTED ANALOGUES OF INS(L,4,5)P3
184 10.3.1 PREPARATION OF METHYL 2-0-BENZYL-3,4-DI-0-(P-METHOXY-
BENZYL)-OC-D-GLUCOPYRANOSIDE 58 185 10.3.2 PREPARATION OF (IR, 2R, 35,
4R, 5S)-3-HYDROXY-1,2,4- TRISPHOSPHO-5-VINYL CYCLOPENTANE 53B 187 10.3.3
PREPARATION OF (IR, 2R, 3S, 4R, 55)-3-HYDROXY-5- HYDROXYMETHYL-1,2,4
TRISPHOSPHO CYCLOPENTANE 75 189 10.4 SYNTHESIS OF A CARBOHYDRATE-BASED
INOSITOL POLYPHOS-PHATE MIMIC BASED ON ADENOPHOSTIN A 191 10.4.1
SYNTHESIS OF 2,6-DI-0-BENZYL-3,4-DI-0-(P-METHOXYBENZYL) -D-
GLUCOPYRANOSE 93 193 10.4.2 SYNTHESIS OF
(2-HYDROXYETHYL)-2 ,3,4-TRISPHOSPHATE-A-D- GLUCOPYRANOSIDE 88 : 197
10.4.3 PREPARATION OF A FLUORESCENT LABEL BASED UPON (2-HYDROXY- ETHYL)-
2 ,3,4-TRISPHOSPHATE-A-D-GLUCOPYRANOSIDE 199 10.5 CONCLUSION 201 10.6
REFERENCES 201 11 CHEMO-ENZYMATIC TOTAL SYNTHESIS OF SOME CONDURITOLS,
CARBASUGARS AND (+)-FORTAMINE 209 L. DUMORTIER, P. LIU, J. VAN DER
EYCKEN AND M. VANDEWALLE * 11.1 INTRODUCTION 209 11.2 RESULTS 209 11.2.1
SUBSTRATES AND ENANTIOSELECTIVE ENZYMATIC HYDROLYSIS 209 11.2.2 THE
SYNTHESIS OF SOME ADVANCED INTERMEDIATES 212 XXII 11.2.3 SYNTHESIS OF
CONDURITOLS 213 11.2.4 SYNTHESIS OF CARBA-SUGARS 214 11.2.5 SYNTHESIS OF
(+)-FORTAMINE (78) 218 11.3 REFERENCES 220 12 CHEMO-ENZYMATIC APPROACHES
TO ENANTIOPURE CARBASUGARS AND CARBANUCLEOSIDES 223 J. BAUMGARTNER AND
H. GRIENGL 12.1 INTRODUCTION 223 12.2 ENANTIOPURE CARBAHEXO- AND
PENTOFURANOSES 225 12.3 INTRODUCTION OF THE BASE 229 12.4 CARBAULOSES
231 12.5 REFERENCES 235 13 GLYCOMIMETICS THAT INHIBIT CARBOHYDRATE
METABOLISM 239 BRUCE GANEM 13.1 INTRODUCTION 239 13.2 STUDIES ON
MANNOSTATIN 241 13.3 ELECTROPHILIC ADDITIONS TO SUBSTITUTED
CYCLOPENTENES 247 13.4 STUDIES ON ALLOSAMIZOLINE: AN AMINOCYCLOPENTITOL
FROM ALLOSAMIDIN 249 13.5 STUDIES ON TREHAZOLIN AND KERRUFARIDE 252 13.6
REFERENCES 255 14 TOWARD AZAGLYCOSIDE MIMICS: AZA-C-GLYCOSYL COMPOUNDS
AND HOMOAZAGLYCOSIDES 259 O. R. MARTIN 14.1 INTRODUCTION , 259 14.2
AZA-C-GLYCOSYL COMPOUNDS 262 14.3 HOMOAZAGLYCOSIDES 270 14.4
1-DEOXYAZASEPTANOSES 276 14.5 CONCLUSION... 279 14.6 REFERENCES 279 15
TOTAL SYNTHESIS AND CHEMICAL DESIGN OF USEFUL GLYCOSIDASE INHIBITORS 283
K. TATSUTA 15.1 INTRODUCTION 283 15.2 RESULTS 284 15.2.1 CYCLOPHELLITOLS
284 XXIII 15.2.2 NAGSTATINS 290 15.2.3 GUALAMYCIN 298 15.3
CONCLUSION.... 304 15.4 REFERENCES 304 16 SYNTHESIS OF ENANTIOPURE
AZASUGARS FROM D-MANNITOL: CARBOHYDRATE AND PEPTIDE MIMICS 307 J. -C.
DEPEZAY 16.1 INTRODUCTION 307 16.2 RESULTS 308 16.2.1 TO AZASUGARS VIA
BIS-AZIRIDINES 308 16.2.1.1 NUCLEOPHILIC OPENING OF BIS-AZIRIDINES 308
16.2.1.2 BIS-AZIRIDINES PRECURSORS OF AZADISACCHARIDES 310 16.2.2 TO
AZASUGARS VIA BIS-EPOXIDES 314 16.2.2.1 NUCLEOPHILIC OPENING OF
BIS-EPOXIDES 314 16.2.2.2 ISOMERISATION OF POLYHYDROXYLATED PIPERIDINES
317 16.2.3 ISOMERISATION OF POLYHYDROXYLATED AZEPANES 320 16.2.4
INHIBITION STUDIES 322 16.2.5 SYNTHESIS OF NON-PEPTIDE MIMICS OF
SOMATOSTATIN 322 16.3 CONCLUSION 325 16.4 REFERENCES 325 17 FURAN-,
PYRROLE-, AND THIOPHENE-BASED SILOXYDIENES EN ROUTE TO CARBOHYDRATE
MIMICS AND ALKALOIDS 327 G. CASIRAGHI, G. RASSU AND F. ZANARDI 17.1
INTRODUCTION 327 17.2 OUTLINE OF THE STRATEGY 328 17.3 SYNTHETIC
APPLICATIONS 330 17.3.1 AMINOSUGAR DERIVATIVES 330 17.3.2
HYDROXYLATEDOC-AMINOACIDS.... 332 17.3.3 BICYCLIC HYDROXYLATED ALKALOIDS
336 17.3.4 NUCLEOSIDES AND NUCLEOSIDE MIMETICS 341 17.4 CONCLUSION 346
17.5 REFERENCES 346 18 TRAVELLING THROUGH THE POTENTIAL ENERGY SURFACE
OF SIALYL LEWIS X 349 A. IMBERTY AND S. PEREZ 18.1 INTRODUCTION 349 XXIV
18.2 COMPUTATIONAL METHODS 351 18.2.1 NOMENCLATURE 351 18.2.2 RELAXED
MAPS OF DISACCHARIDES 351 18.2.3 CALCULATION OF POTENTIAL ENERGY SURFACE
USING CICADA 351 18.2.4 DETERMINATION OF FAMILY OF LOW ENERGY CONFORMERS
352 18.2.5 FLEXIBILITY INDEXES 352 18.2.6 CALCULATING MOLECULAR
PROPERTIES 352 18.3 RESULTS AND DISCUSSION 352 18.3.1 ANALYSIS OF THE
LINKAGES CONFORMATION 353 18.3.2 FAMILIES OF CONFORMERS AND ENERGY
MINIMA 356 18.3.3 FLEXIBILITY 359 18.3.4 MOLECULAR PROPERTIES 360 18.4
CONCLUSION 362 18.5 REFERENCES 362 19 SYNTHESES OF SULFATED DERIVATIVES
AS SIALYL LEWIS 3 AND SIALYL LEWIS X ANALOGUES 365 C. AUGE, F. DAGRON,
R. LEMOINE, C. LE NARVOR AND A. LUBINEAU 19.1 INTRODUCTION 365 19.2
SYNTHESIS OF 3 -SULFATED LEWIS A TRISACCHARIDE AND PENTASACCHARIDE 367
19.2.1 3 -SULFATED LEWIS A TRISACCHARIDE 367 19.2.2 3 -SULFATED LEWIS A
PENTASACCHARIDE 368 19.3 REGIOSELECTIVE SULFATION 369 19.3.1 STANNYLENE
METHODOLOGY 369 19.3.2 CYCLIC SULFATES 371 19.4 POLYSULFATED
OLIGOSACCHARIDES IN THE LEWIS X SERIES 372 19.4.1 INTRODUCTION 372
19.4.2 6 -SULFATED, 3 -SULFATED, 3 ,6 -DISULFATED LEWIS X PENTASACCHA-
RIDES 373 19.4.3 3 ,6-DISULFATED LEWIS X PENTASACCHARIDE 376 19.5
IMMUNOLOGICAL STUDIES 379 19.5.1 SPECIFICITY OF THE E-SELECTIN 379
19.5.2 SPECIFICITY OF THE L-SELECTIN 381 19.6 REFERENCES 382 20
ARCHITECTONIC NEOGLYCOCONJUGATES: EFFECTS OF SHAPES AND VALENCIES IN
MULTIPLE CARBOHYDRATE-PROTEIN INTERACTIONS 385 XXV D. ZANINI AND R. ROY
20.1 INTRODUCTION 385 20.2 NEOGLYCOPROTEINS AND GLYCOPOLYMERS 387 20.3
GLYCOTELOMERS 390 20.4 GLYCOPEPTOIDS 391 20.5 GLYCOCLUSTERS 393 20.6
CYCLIC GLYCOPEPTIDES 395 20.7 GLYCODENDRIMERS 397 20.8 SPHERICAL
GLYCODENDRIMERS 402 20.9 CYCLODEXTRINS AND GLYCOCALIXARENES 407 20.10
BIOLOGICAL TESTING 409 20.11 CONCLUSION 410 20.12 REFERENCES 410 21 FROM
GLYCOSAMINOGLYCANS TO HEPARINOID MIMETICS WITH ANTIPROLIFERATIVE
ACTIVITY 417 H. P. WESSEL, A. CHUCHOLOWSKI, J. FINGERLE, N. IBERG, H. P.
MDRKI, R. MIILLER, M. PECH, M. PFISTER-DOWNAR, M. ROUGE, G. SCHMID AND
T. TSCHOPP 21.1 INTRODUCTION 417 21.2 SULFATED CARBOHYDRATES 417 21.3
SPACED SUGARS 424 21.4 A NEW APPROACH TO OLIGOSACCHARIDE MIMETICS 428
21.5 REFERENCES 429 22 CONDURITOLS AND ANALOGUES AS INSULIN MODULATORS
433 D.C. BILLINGTON, F. PERRON-SIERRA, I. PICARD, S. BEAUBRAS, J.
DUHAULT, J. ESPINAL AND S. CHALLAL 22.1 INTRODUCTION 433 22.2 RESULTS
434 22.3 REFERENCES AND NOTES 440 23 STRATEGIES FOR THE SYNTHESIS OF
INOSITOL PHOSPHO-GLYCAN SECOND MESSENGERS 443 N. KHIAR AND M.
MARTIN-LOMAS 23.1 INTRODUCTION 443 23.2 THE STRUCTURE OF THE INOSITOL
PHOSPHOGLYCAN WHICH MEDIATES THE INTRACELLULAR POST-RECEPTOR ACTION OF
INSULIN 446 XXVI 23.3 THE SYNTHESIS OF BUILDING BLOCKS FOR THE
PREPARATION OF INOSITOLPHOSPHOGLYCAN SECOND MESSENGERS 447 23.3.1
SYNTHESIS OF CONVENIENTLY FUNCTIONALISED ENANTIOMERICALLY PURE D-MYO OR
D-CHIRO INOSITOL DERIVATIVES 447 23.3.2 SYNTHESIS OF CONVENIENTLY
FUNCTIONALISED GLUCOSAMINE UNIT 450 23.3.3 SYNTHESIS OF
6-O-GLYCOSYL-D-C/Z/RO AND D-WYO-INOSITOL DERIVATIVES 450 23.4 EVALUATION
OF THE INSULIN-LIKE ACTIVITY OF 4-0-GLUCO-SAMINE- MYO-INOSITOL-
1-PHOSPHATE, 6-O-GLUCOSAMINE-MYO-INOSITOL-1- PHOSPHATE,
6-0-GLUCOSAMINE-/NYO-INOSITOL-1,2-CYCLIC PHOSPHATE 452 23.5 TOWARD THE
TOTAL SYNTHESIS OF THE PSEUDO OCTA-SACCHARIDE V, PUTATIVE SECOND
MESSENGER OF THE HORMONE INSULIN 454 23.5.1 SYNTHESIS OF THE
TETRASACCHARIDE VII [31] 454, 23.5.2 SYNTHESIS OF THE TETRASACCHARIDE
VII 457 23.6 CONCLUSION 459 23.7 REFERENCES 460 24 THE CATALYTIC
EFFICIENCY OF GLYCOSIDE HYDROLASES AND MODELS OF THE TRANSITION STATE
BASED ON SUBSTRATE RELATED INHIBITORS 463 G. LEGLER 24.1 INTRODUCTION
463 24.2 CATALYTIC EFFICIENCY AND THE TRANSITION STATE 464 24.2 EVIDENCE
FOR A GLYCOSYL CATION-LIKE TRANSITION STATE 468 24.3 EVIDENCE FOR ACTIVE
SITE CARBOXYLATE GROUPS 472 24.4 INTERACTIONS WITH THE AGLYCON SITE 481
24.5 NL-ALKYL GLUCONAMINIDINES AS PERFECT TRANSITION STATE MIMICS? 483
24.6 CONCLUSION 485 24.7 REFERENCES 487 25 DESIGN AND SYNTHESIS OF
POTENTIAL FUCOSYL TRANSFERASE INHIBITORS 491 G. A. VAN DER MAREL, B. M.
HESKAMP, G. H. VEENEMAN, C. A. A. VAN BOECKEL AND J. H. VAN BOOM* 25.1
INTRODUCTION 491 25.1.1 ROLE OF SELECTINS IN LEUCOCYTE EXTRAVASATION 491
25.2 RECEPTOR-BASED ADHESION INHIBITION 494 XXVII 25.2.1 LIGAND-BASED
ADHESION INHIBITION 494 25.2.2 FUCOSYLTRANSFERASE INHIBITORS 498 25.3
CONCLUSION 505 25.4 REFERENCES 506 26 ENZYMATIC SYNTHESIS OF LACTOSE
ANALOGUES USING GLYCOSIDASES 511 A. FERNANDEZ-MAYORALAS 26.1
INTRODUCTION 511 26.2 RESULTS AND DISCUSSION 514 26.4 CONCLUSION 521
26.5 REFERENCES 521 27 SYNTHESIS OF NITROGEN CONTAINING LINKERS FOR
ANTISENSE OLIGONUCLEOTIDES 523 YOGESH S. SANGHVI 21. INTRODUCTION 523
27.2 RESULTS 524 27.2.1 3 -C-N-0 LINKED BACKBONES 524 27.2.1.1 SYNTHESIS
OF OXIME DIMER 5 525 27.2.1.2 SYNTHESIS OF MI DIMER 6 526 27.2.1.3
SYNTHESIS OF MMI DIMER 7 527 27.2.2 3 -C-N-N LINKED BACKBONE 527
27.2.2.1 SYNTHESIS OF MDH DIMER 8 527 27.2.3 3 -C-O-N LINKED BACKBONE
528 27.2.3.1 SYNTHESIS OF MOMIDIMER 9 528 27.2.4 3 -O-N-C LINKED
BACKBONE 529 27.2.4.1 SYNTHESIS OF HMIM DIMER 10 529 27.2.5 3 -C-N-C AND
C-C-N LINKED BACKBONE 531 27.2.5.1 SYNTHESIS OF AMINE 1 AND 2 DIMERS (11
AND 12) 531 27.2.6 2 -OME 3 - C-N-0 LINKED BACKBONE 532 27.2.6.1
SYNTHESIS OF BIS 2 -OME MMI LINKED DIMER 13 532 27.3 CONCLUSION 534 27.4
REFERENCES 535 28 NUCLEOSIDES AND NUCLEOTIDES CONTAINING 5-ALKYL
PYRIMIDINES. CHEMISTRY AND MOLECULAR PHARMACOLOGY 537 L. OTVOS 28.1
CHEMISTRY 537 XXVIII 28.1.1 SYNTHETIC METHODS 538 28.1.2 DEACYLATION OF
DERIVATIVES IN THE SUGAR MOIETY 540 28.2 BIOORGANIC CHEMISTRY 542 28.2.1
SUBSTRATE SPECIFICITY IN POLYMERASE CATALYSED REACTIONS 542 28.2.1.1
5-N-ALKYL-, 5-(N-L-ALKENYL)- AND 5-(N-L-ALKYNYL)DUTPS 543 28.2.1.2
DEOXYURIDINES CONTAINING BRANCHED SUBSTITUENTS IN POSITION 5 547 28.2.2
STRUCTURAL PROPERTIES AND STABILITY OF POLYNUCLEOTIDES CONTAINING
5-ALKYL-2 -DEOXYURIDINES 548 28.3 MOLECULAR PHARMACOLOGY 549 28.3.1
MOLECULAR PHARMACOLOGY OF THE ANTIHERPETIC ACTIVITY OF 5-
ISOPROPYL-2 -DEOXYURIDINE 549 28.3.2 ANTISENSE DRUG PROPERTIES OF
OLIGONUCLEOTIDES CONTAINING 5- ALKYL-2 -DEOXYURIDINES 550 28.4
REFERENCES 551 29 ANHYDROHEXITOLS AS CONFORMATIONALLY CONSTRAINED
FURANOSE MIMICS, DESIGN OF AN RNA-RECEPTOR 553 P. HERDEWIJN 29.1
INTRODUCTION 553 29.2 DOUBLE STRANDED RNA STRUCTURE 556 29.3 DESIGN OF
OLIGONUCLEOTIDES WITH A SIX MEMBERED CARBOHYDRATE MOIETY 558 29.4
SYNTHESIS OF 2 ,3 -DIDEOXY-3 -C-HYDROXYMETHYL-A-L-F/IREO- PENTOPYRANOSYL
NUCLEOSIDE AND L,5-ANHYDRO-2,3-DIDEOXY-D- ARABINO-HEXITOL NUCLEOSIDE 562
29.5 OLIGONUCLEOTIDE BUILT UP FROM NUCLEOSIDES WITH A SIX- MEMBERED
CARBOHYDRATE-LIKE MOIETY 569 29.6 1,5-ANHYDROHEXITOL NUCLEOSIDE AS A
MIMIC OF A FURANOSE NUCLEOSIDE IN ITS 2 -ENDO/3 -EXO CONFORMATION 573
29.7 REFERENCES 579 INDEX 581
|
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| genre_facet | Konferenzschrift |
| id | DE-604.BV011663256 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T18:13:40Z |
| institution | BVB |
| isbn | 3527295267 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-007863521 |
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| spelling | Carbohydrate mimics concepts and methods ed. by Yves Chapleur Weinheim [u.a.] Wiley-VCH 1998 XVIII, 604 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Glucides - Synthèse ram Glucides ram Carbohydrates Congresses Carbohydrates Synthesis Congresses Carbohydrates chemical synthesis Congresses Carbohydrates chemistry Congresses Mimicry (Chemistry) Congresses Kohlenhydrate (DE-588)4164517-0 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Modifizierte Verbindungen (DE-588)4483702-1 gnd rswk-swf (DE-588)1071861417 Konferenzschrift gnd-content Kohlenhydrate (DE-588)4164517-0 s Modifizierte Verbindungen (DE-588)4483702-1 s Chemische Synthese (DE-588)4133806-6 s DE-604 Chapleur, Yves Sonstige oth HEBIS Datenaustausch Darmstadt application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007863521&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Carbohydrate mimics concepts and methods Glucides - Synthèse ram Glucides ram Carbohydrates Congresses Carbohydrates Synthesis Congresses Carbohydrates chemical synthesis Congresses Carbohydrates chemistry Congresses Mimicry (Chemistry) Congresses Kohlenhydrate (DE-588)4164517-0 gnd Chemische Synthese (DE-588)4133806-6 gnd Modifizierte Verbindungen (DE-588)4483702-1 gnd |
| subject_GND | (DE-588)4164517-0 (DE-588)4133806-6 (DE-588)4483702-1 (DE-588)1071861417 |
| title | Carbohydrate mimics concepts and methods |
| title_auth | Carbohydrate mimics concepts and methods |
| title_exact_search | Carbohydrate mimics concepts and methods |
| title_full | Carbohydrate mimics concepts and methods ed. by Yves Chapleur |
| title_fullStr | Carbohydrate mimics concepts and methods ed. by Yves Chapleur |
| title_full_unstemmed | Carbohydrate mimics concepts and methods ed. by Yves Chapleur |
| title_short | Carbohydrate mimics |
| title_sort | carbohydrate mimics concepts and methods |
| title_sub | concepts and methods |
| topic | Glucides - Synthèse ram Glucides ram Carbohydrates Congresses Carbohydrates Synthesis Congresses Carbohydrates chemical synthesis Congresses Carbohydrates chemistry Congresses Mimicry (Chemistry) Congresses Kohlenhydrate (DE-588)4164517-0 gnd Chemische Synthese (DE-588)4133806-6 gnd Modifizierte Verbindungen (DE-588)4483702-1 gnd |
| topic_facet | Glucides - Synthèse Glucides Carbohydrates Congresses Carbohydrates Synthesis Congresses Carbohydrates chemical synthesis Congresses Carbohydrates chemistry Congresses Mimicry (Chemistry) Congresses Kohlenhydrate Chemische Synthese Modifizierte Verbindungen Konferenzschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007863521&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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