Biosynthesis of heterocycles : from the isolation to gene cluster

783 Pages·2015·23.841 MB·English

by  Cirrincione, Girolamo, Diana, Patrizia

BIOSYNTHESIS OF
HETEROCYCLES

BIOSYNTHESIS OF
HETEROCYCLES
From Isolation to Gene Cluster
PATRIZIADIANA
GIROLAMOCIRRINCIONE
DipartimentodiScienzeeTecnologieBiologicheChimichee
Farmaceutiche(STEBICEF)UniversitàdegliStudidiPalermo
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LibraryofCongressCataloging-in-PublicationData:
Diana,Patrizia.
Biosynthesisofheterocycles:fromtheisolationtogenecluster/PatriziaDiana,GirolamoCirrincione.
pagescm
“AJohnWiley&Sons,Inc.,publication.”
Includesbibliographicalreferencesandindex.
ISBN978-1-118-02867-4(cloth)
1.Heterocycliccompounds–Synthesis.2.Biosynthesis.I.Cirrincione,Girolamo.II.Title.
QD400.5.S95D532015
547’.59–dc23
2014023088
Typesetin10/12ptTimesLTStdbyLaserwordsPrivateLimited,Chennai,India
PrintedintheUnitedStatesofAmerica
10987654321
1 2015
ToGabriella,Giovanni,andlittleVincenzo.

CONTENTS
PREFACE xiii
ACKNOWLEDGMENTS xv
1 Introduction 1
1.1 NaturalProducts:PrimaryandSecondaryMetabolites, 4
1.2 CommonReactionsinSecondaryMetabolites, 6
1.2.1 Alkylations, 6
1.2.2 Wagner–MeerweinRearrangements, 16
1.2.3 AldolandClaisenReactions, 17
1.2.4 SchiffBaseFormationandMannichReactions, 23
1.2.5 Transaminations, 25
1.2.6 Decarboxylations, 26
1.2.7 OxidationandReductionReactions, 31
1.2.8 Dehalogenation/HalogenationReactions, 39
1.2.9 GlycosylationReactions, 46
References, 48
2 TechniquesforBiosynthesis 51
2.1 IsotopicLabeling, 52
2.1.1 StableIsotopes, 52
2.1.2 RadioactiveIsotopes, 61
2.2 GeneCodingforEnzymes, 62
2.3 CombinatorialBiosynthesis, 63
References, 70
vii
viii CONTENTS
3 Three-MemberedHeterocyclicRingsandTheirFusedDerivatives 73
3.1 AziridinesandAzirines, 73
3.1.1 Azicemicins, 73
3.1.2 Miraziridine, 74
3.1.3 Maduropeptin, 75
3.1.4 Azinomycins, 79
3.1.5 Ficellomycin, 87
3.1.6 Mitomycins, 89
3.1.7 AzirinomycinandRelatedAzirines, 101
3.2 OxiranesandOxirenes, 104
3.2.1 Fosfomycin, 104
3.2.2 AK,HC,andAFtoxins, 111
3.2.3 Cerulenin, 117
3.2.4 Polyhydroxyalkanoates, 118
3.2.5 Epoxyrollins, 118
3.2.6 Asperlactone,Aspyrone,Asperline, 121
3.2.7 Tajixanthone, 129
3.2.8 Cyclomarin, 133
3.2.9 Cyclopenin, 139
3.2.10 OvalicinandFumagillin, 141
3.2.11 MethylenomycinA, 143
3.2.12 AntibioticLL-C10037, 147
3.2.13 Manumycins, 151
3.2.14 Scopolamine, 164
3.2.15 IridoidGlucosides, 169
3.2.16 Cordiaquinone, 172
3.2.17 CyclizidineandIndolizomycin, 172
3.2.18 EnediyneAntibiotics, 175
3.2.19 Macrolides, 195
3.2.20 Epothilones, 225
3.2.21 Pimaricin, 233
3.2.22 Hypothemycin, 240
3.2.23 RadicicolandMonocillinI, 243
3.2.24 Trichothecenes, 248
3.2.25 SporolidesAandB, 255
References, 258
4 Four-MemberedHeterocyclicRingsandTheirFusedDerivatives 277
4.1 AzetidineandAzetines, 277
4.1.1 Azetidine-2-carboxylicacid, 277
4.1.2 Polyoxins, 280
4.1.3 MugineicAcids, 288
4.1.4 TabtoxinandTabtoxinine-β-lactam, 293