Methods in Chromatography - Vol 2 : Porphyrins

Porphyrins

By: Chang-Kee Lim

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Hardcover | 1 December 2008

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The porphyrins, chlorophylls, bilins and related tetrapyrroles are vital for all living organisms. Natural and synthetic tetrapyrroles are used extensively in foods, cosmetics, biotechnology, pharmaceuticals, diagnostics and medicine. Methods for their separation and characterization therefore, have a very wide area of applications. Yet, there is a dearth of books dedicated to HPLC and HPLC/MS of tetrapyrroles. Lim addresses this problem admirably by providing practical HPLC and HPLC/MS protocols coupled with in-depth chromatographic and mass spectrometric reference data. These are invaluable in the analysis, identification and characterization of porphyrins, chlorophylls, bilins and other related compounds found in biological and clinical materials. HPLC method development and optimization for coupling to mass spectrometry are also described in rich detail. Sample preparation, and suggestions for avoiding procedural artifacts during extraction of clinical and biological samples are discussed. Clinical biochemists involved in biochemical diagnosis of human porphyrias will find this monograph assuredly helpful, as would analysts, biochemists and chemists involved in the separation, isolation and characterization of natural and synthetic tetrapyrroles. Undoubtedly, Lim has contributed a master-piece containing sufficient background material for beginners and up-to-date references for all researchers in the field. Book jacket.

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Preface	p. v
Structure, Distribution, Biosynthesis and Function	p. 1
Introduction	p. 1
Nomenclature	p. 2
Biosynthesis of Porphyrins, Haem and Chlorophyll	p. 3
Biosynthesis of Bilins in Animals and Plants	p. 9
Degradation of haem to bile pigments	p. 9
Biosynthesis of bilins in plants, algae and cyanobacteria	p. 11
Degradation of chlorophyll in senescent higher plants	p. 13
Function of Porphyrins and Other Tetrapyrroles	p. 15
High-Performance Liquid Chromatography of Porphyrins	p. 25
Introduction	p. 25
HPLC of Porphyrin Methyl Esters	p. 26
HPLC of Porphyrin Free Acids	p. 27
Stationary phases for reversed-phase HPLC of porphyrins	p. 28
Mobile phases for reversed-phase HPLC of porphyrins	p. 29
Procedure for optimisation of porphyrin separation by reversed-phase HPLC	p. 32
Retention behaviour of porphyrins in reversed-phase HPLC	p. 34
HPLC of Porphyrinogens	p. 40
Mass Spectrometry of Porphyrins	p. 51
Introduction	p. 51
Fast Atom Bombardment (FAB) Mass Spectrometry of Porphyrins	p. 52
Laser Desorption/lonisation Time-of-Flight (LDI-TOF) Mass Spectrometry of Porphyrins	p. 52
Electrospray lonisation Mass Spectrometry (ESI-MS) and HPLC/ESI-MS of Porphyrins	p. 56
HPLC/ESI-MS of porphyrins	p. 58
ESI-MS/MS fragmentation of porphyrins	p. 64
ESI-MS/MS production spectrum and fragmentation pathways of uroporphyrin	p. 65
ESI-MS/MS fragmentation of hydroxyuroporphyrins	p. 65
ESI-MS/MS product ion spectrum and fragmentation pathways of meso-hydroxyuroporphyrin	p. 67
ESI-MS/MS product ion spectrum of hydroxyacetic acid uroporphyrin	p. 69
ESI-MS/MS product ion spectrum of ¿-hydroxypropionic acid uroporphyrin	p. 71
ESI-MS/MS product ion spectrum and fragmentation pathways of ß-hydroxypropionic acid uroporphyrin	p. 71
ESI-MS/MS product ion spectra and fragmentation pathways of cis- and trans- hydroxyspirolactoneurochlorins	p. 74
ESI-MS/MS product ion spectra and fragmentation pathways of cis- and trans-dihydroxyurochlorins	p. 75
Characteristic ESI-MS/MS productions of hydroxyuroporphyrins	p. 80
ESI-MS/MS product ion spectra of ketoacid uroporphyrins	p. 80
ESI-MS/MS of heptacarboxylic porphyrin	p. 83
ESI-MS/MS of hydroxyheptacarboxylic porphyrins	p. 86
ESI-MS/MS of ketoacid heptacarboxylic porphyrins and formyl heptacarboxylic porphyrin	p. 86
ESI-MS/MS product ion spectrum and fragmentation pattern of coproporphyrin	p. 89
ESI-MS/MS of hydroxymethylcoproporphyrin	p. 93
ESI-MS/MS of ß-ketopropionic acid coproporphyrin and formylcoproporphyrin	p. 93
ESI-MS/MS product ion spectrum and fragmentation pattern of protoporphyrin	p. 93
HPLC/ESI-MS and MS/MS of meso-tetraphenylporphyrin derivatives	p. 97
Porphyrin Profiles in Blood, Urine and Faeces by HPLC and HPLC/ESI-MS	p. 107
Introduction	p. 107
Sample Collection and Preparation	p. 108
Preparation of urine samples	p. 109
Preparation of faecal sample	p. 110
Extraction of porphyrins in plasma	p. 111
Extraction of red blood cell porphyrins	p. 112
Porphyrin Excretion Patterns and Enzyme Assays in the Porphyrias	p. 113
Aminolaevulinic acid dehydratase deficiency porphyria (ADP)	p. 113
Determination of ALA and PBG	p. 113
Determination of erythrocyte Zn-protoporphyrin by HPLC	p. 119
Acute intermittent porphyria (AIP)	p. 119
Congenital erythropoietic porphyria (CEP)	p. 123
Porphyria cutanea tarda (PCT)	p. 127
Determination of uroporphyrinogen decarboxylase activity in erythrocytes by HPLC	p. 133
Hereditary coproporphyria (HCP)	p. 135
HPLC assay of coproporphyrinogen oxidase activity in peripheral leucocytes	p. 140
Variegate porphyria (VP)	p. 143
Determination of protoporphyrinogen oxidase by HPLC	p. 144
Erythropoietic protoporphyria (EPP)	p. 146
HPLC assay for ferrochelatase in leucocytes or lymphocytes	p. 147
Mixed porphyria	p. 149
Isolation and Characterisation of Protoporphyrin Glycoconjugates from Harderian Glands of Rodents by HPLC and HPLC/ESI-MS	p. 155
Introduction	p. 155
Extraction of Porphyrins from Harderian Glands	p. 159
HPLC Separation of Porphyrins from Rat Harderian Gland Extract	p. 160
Identification of Protoporphyrin Glycoconjugates from Rat Harderian Glands by Capillary Electrophoresis and HPLC/ESI-MS	p. 162
Characterisation of protoporphyrin xyloside isolated from Harderian glands	p. 166
Characterisation of protoporphyrin monoglucoside isolated from Harderian glands of the rat	p. 172
Origin and Function of Protoporphyrin Glycoconjugates in Harderian Glands of Rodents	p. 173
HPLC and HPLC/MS of Chlorophyll and Related Compounds	p. 177
Introduction	p. 177
Reversed-Phase HPLC of Chlorophyll and Related Compounds in Plant Extracts	p. 177
Normal-Phase HPLC of Chlorophyll and Related Compounds	p. 181
HPLC Separation of Fluorescent and Non-Fluorescent Chlorophyll Catabolites	p. 183
HPLC/MS and MS/MS of Chlorophyll and Related Compounds	p. 185
HPLC and HPLC/MS of Bilins of Animal and Plant Origin	p. 191
Introduction	p. 191
HPLC Separation of Bilirubin III¿, IX¿ and XIII¿ Isomers	p. 191
HPLC Separation of Bilirubin Conjugates	p. 194
HPLC of Biliverdins	p. 195
HPLC of Biliviolins	p. 198
HPLC of Urobilinoids	p. 198
Analysis and Determination of Bile Pigments in Biological and Clinical Samples by HPLC	p. 201
HPLC methods for the determination of conjugated and unconjugated bilirubin in serum	p. 202
Extraction and determination of conjugated and unconjugated bilirubin in serum following trans-esterification	p. 203
Solid-phase extraction (SPE) and determination of conjugated and unconjugated bilirubin in serum	p. 204
Simultaneous determination of conjugated bilirubin, unconjugated bilirubin and biliprotein or ¿-bilirubin by direct injection HPLC	p. 207
HPLC/ESI-MS and MS/MS of Bile Pigments	p. 208
Characterisation of Tetrapyrrole Pigments in Avian Eggshells	p. 212
Extraction of pigments from eggshells	p. 213
HPLC and HPLC/MS of Phycobilins	p. 217
HPLC separation of Phycobiliproteins	p. 217
Future Directions of HPLC and Mass Spectrometry of Tetrapyrroles	p. 223
Index	p. 227
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Methods in Chromatography - Vol 2 : Porphyrins

Porphyrins

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Hardcover

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