Plant nucleotide metabolism biosynthesis, degradation and alkaloid formation

455 Pages·2020·10.409 MB·English

by  Ashihara, Hiroshi, Crozier, Alan, Ludwig, Iziar A

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PlantNucleotideMetabolism–Biosynthesis,
Degradation,andAlkaloidFormation
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Plant Nucleotide Metabolism – Biosynthesis,
Degradation, and Alkaloid Formation
HiroshiAshihara
OchanomizuUniversity
Bunkyo-ku,Tokyo,Japan
IziarA.Ludwig
UniversityRoviraI
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Virgili
Reus,Spain
AlanCrozier
UniversityofCalifornia
Davis,CA,USA
UniversityofGlasgow
Glasgow,UK
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Thiseditionfirstpublished2020
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LibraryofCongressCataloging-in-PublicationData
Name:Ashihara,Hiroshi,author.
Title:Plantnucleotidemetabolism:biosynthesis,degradation,andalkaloidformation/HiroshiAshihara,
EmeritusProfessor,OchanomizuUniversity,Tokyo,Japan,IziarA.Ludwig,UniversityRoviraI,Virgili,
Spain,AlanCrozier,UniversityofCalifornia,DavisandUniversityofGlasgow,UK.
Description:Firstedition.|Hoboken:Wiley,2020.|Includesbibliographicalreferencesandindex.
Identifiers:LCCN2019047672(print)|LCCN2019047673(ebook)|ISBN9781119476122(hardback)|
ISBN9781119476108(adobepdf)|ISBN9781119476078(epub)
Subjects:LCSH:Plants–Metabolism.|Nucleotides–Metabolism.
Classification:LCCQK881.A742020(print)|LCCQK881(ebook)|DDC572/.42–dc23
LCrecordavailableathttps://lccn.loc.gov/2019047672
LCebookrecordavailableathttps://lccn.loc.gov/2019047673
CoverDesign: Wiley
CoverImage: ©MazurTravel/Shutterstock
Setin10/12ptWarnockProbySPiGlobal,Chennai,India
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Contents
Preface xv
PartI GeneralAspectsofNucleotideMetabolism 1
1 StructuresofNucleotide-RelatedCompounds 3
1.1 Introduction 3
1.2 NomenclatureandAbbreviationsofNucleotide-RelatedCompounds 3
1.3 ChemicalStructuresofNucleotide-RelatedCompounds 5
1.3.1 Purines 5
1.3.1.1 PurineBases 5
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1.3.1.2 PurineNucleosides 6
1.3.1.3 PurineNucleotides 7
1.3.2 Pyrimidines 8
1.3.2.1 PyrimidineBases 9
1.3.2.2 PyrimidineNucleosides 9
1.3.2.3 PyrimidineNucleotides 10
1.3.3 Pyridines 11
1.4 Summary 11
References 11
2 OccurrenceofNucleotidesandRelatedMetabolitesinPlants 13
2.1 PurinesandPyrimidines 13
2.1.1 ConcentrationofPurineandPyrimidineNucleotides 14
2.1.2 ConcentrationofPurineandPyrimidineBasesandNucleosides 16
2.2 PyridineNucleotides 17
2.2.1 ConcentrationofPyridineNucleotides 17
2.2.2 ConcentrationofNicotinateandNicotinamide 18
2.3 ConcentrationofCytokinins 18
2.4 AlkaloidsDerivedfromNucleotides 18
2.5 Summary 19
References 19
3 GeneralAspectsofNucleotideBiosynthesis
andInterconversions 21
3.1 Introduction 21
3.2 DeNovoBiosynthesisofRibonucleosideMonophosphates 21
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3.3 InterconversionofNucleosideMonophosphates,NucleosideDiphosphates,
andTriphosphates 23
3.3.1 Nucleoside-MonophosphateKinase 23
3.3.2 SpecificNucleoside-MonophosphateKinases 24
3.4 ConversionofNucleosideDiphosphatestoNucleosideTriphosphates 24
3.4.1 ATPSynthesisbyElectronTransferSystems 25
3.4.2 Substrate-LevelATPSynthesis 26
3.4.3 Nucleoside-DiphosphateKinase 26
3.5 BiosynthesisofDeoxyribonucleotides 29
3.6 NucleicAcidBiosynthesis 29
3.7 Supplyof5-Phosphoribosyl-1-Pyrophosphate 30
3.8 SupplyofAminoAcidsforNucleotideBiosynthesis 33
3.9 NitrogenMetabolismandAminoAcidBiosynthesisinPlants 33
3.10 Summary 34
References 35
PartII PurineNucleotideMetabolism 39
4 PurineNucleotideBiosynthesisDeNovo 41
4.1 Introduction 41
4.2 ReactionsandEnzymes 43
(cid:2) 4.2.1 SynthesisofPhosphoribosylamine 44 (cid:2)
4.2.2 SynthesisofGlycineamideRibonucleotide 46
4.2.3 SynthesisofFormylglycineamideRibonucleotide 46
4.2.4 SynthesisofFormylglycinamidineRibonucleotide 47
4.2.5 SynthesisofAminoimidazoleRibonucleotide 47
4.2.6 SynthesisofAminoimidazoleCarboxylateRibonucleotide 48
4.2.7 SynthesisofAminoimidazoleSuccinocarboxamideRibonucleotide 48
4.2.8 SynthesisofAminoimidazoleCarboxamideRibonucleotide 49
4.2.9 SynthesisofIMPviaFormamidoimidazoleCarboxamideRibonucleotide 49
4.2.10 SynthesisofAMP 50
4.2.11 SynthesisofGMP 51
4.3 Summary 52
References 52
5 SalvagePathwaysofPurineNucleotideBiosynthesis 55
5.1 Introduction 55
5.2 CharacteristicsofPurineSalvageinPlants 56
5.3 PropertiesofPurinePhosphoribosyltransferases 59
5.3.1 AdeninePhosphoribosyltransferase 59
5.3.2 Hypoxanthine/GuaninePhosphoribosyltransferase 59
5.3.3 XanthinePhosphoribosyltransferase 62
5.4 PropertiesofNucleosideKinases 62
5.4.1 AdenosineKinase 62
5.4.2 Inosine/GuanosineKinase 64
5.4.3 DeoxyribonucleosideKinases 64
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5.5 PropertiesofNucleosidePhosphotransferase 65
5.6 RoleofPurineSalvageinPlants 66
5.7 Summary 66
References 66
6 InterconversionofPurineNucleotides 71
6.1 Introduction 71
6.2 DeaminationReactions 71
6.2.1 RoutesofDeaminationofAdenineRing 73
6.2.2 AMPDeaminase 73
6.2.3 RoutesofDeaminationofGuanineRing 74
6.2.4 GuanosineDeaminase 75
6.3 DephosphorylationReactions 75
6.4 GlycosidicBondCleavageReactions 76
6.4.1 AdenosineNucleosidase 76
6.4.2 Inosine/GuanosineNucleosidase 78
6.4.3 Non-specificPurineNucleosidases 78
6.4.4 RecombinantNon-SpecificNucleosidases 78
6.5 InSituMetabolismof14C-LabelledPurineNucleotides 79
6.5.1 MetabolismofAdenineNucleotides 79
6.5.2 MetabolismofGuanineNucleotides 80
6.6 InSituMetabolismofPurineNucleosidesandBases 80
(cid:2) 6.6.1 MetabolismofAdenineandAdenosine 82 (cid:2)
6.6.2 MetabolismofGuanineandGuanosine 83
6.6.3 MetabolismofHypoxanthineandInosine 84
6.6.4 MetabolismofXanthineandXanthosine 84
6.6.5 MetabolismofDeoxyadenosineandDeoxyguanosine 85
6.7 Summary 88
References 89
7 DegradationofPurineNucleotides 95
7.1 Introduction 95
7.2 (S)-AllantoinBiosynthesisfromXanthine 97
7.2.1 XanthineDehydrogenase 99
7.2.2 UrateOxidase 100
7.2.3 AllantoinSynthase 101
7.3 Catabolismof(S)-Allantoin 101
7.3.1 Allantoinase 103
7.3.2 AllantoateAmidohydrolase 104
7.3.3 (S)-UreidoglycineAminohydrolase 104
7.3.4 AllantoateAmidinohydrolase 105
7.3.5 UreidoglycolateAmidohydrolase 105
7.3.6 (S)-Ureidoglycolate-ureaLyase 105
7.3.7 Urease 105
7.4 PurineNucleotideCatabolisminPlants 106
7.5 AccumulationandUtilizationofUreidesinPlants 107
7.5.1 UreidesinPlantTissuesandXylemSap 107
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7.5.2 RoleofUreidesinNitrogenStorageandTransport 109
7.5.3 RoleofUreidesinGerminationandDevelopmentofSeeds 109
7.5.4 UreideFormationinNodulesofTropicalLegumes 110
7.5.5 OtherRoleofUreidesinPlants 110
7.6 Summary 111
References 111
PartIII PyrimidineNucleotideMetabolism 117
8 PyrimidineNucleotideBiosynthesisDeNovo 119
8.1 Introduction 119
8.2 ReactionsandEnzymesoftheDeNovoBiosynthesis 121
8.2.1 SynthesisofCarbamoyl-phosphate 121
8.2.2 FormationofCarbamoyl-aspartate 123
8.2.3 FormationofDihydroorotasefromCarbamoyl-aspartate 123
8.2.4 FormationofOrotatefromDihydroorotate 124
8.2.5 SynthesisofUMPfromOrotate 125
8.2.6 SynthesisofCTPfromUTP 126
8.3 ControlMechanismofDeNovoPyrimidineRibonucleotide
Biosynthesis 127
8.3.1 FineControloftheDeNovoPathway 127
(cid:2) 8.3.2 CoarseControloftheDeNovoPathway 129 (cid:2)
8.4 BiosynthesisofThymidineNucleotide 129
8.4.1 FormationofdUMP 129
8.4.2 ConversionofUMPtodUMPviadUTP 130
8.4.3 ConversionofdUMPtodTMP 130
8.4.4 ThymidineMonophosphateKinase 131
8.5 Summary 131
References 131
9 SalvagePathwaysofPyrimidineNucleotideBiosynthesis 137
9.1 Introduction 137
9.2 CharacteristicsofPyrimidineSalvageinPlants 137
9.3 EnzymesofPyrimidineSalvage 139
9.3.1 UracilPhosphoribosylTransferase 140
9.3.2 Uridine/CytidineKinase 142
9.3.3 ThymidineKinase 143
9.3.4 DeoxyribonucleosideKinase 144
9.3.5 NucleosidePhosphotransferase 144
9.4 RoleofPyrimidineSalvageinPlants 145
9.5 Summary 146
References 146
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