INDEX 365 Dihydrokaempferol, and isoflavone Electrocyclic addition, in nonadride biosynthesis, 73, 74 biosynthesis, 188 3,10 - Dihydroperylene - 4,9 - quinone, Electronic spectra of annulenes, and biosynthesis of, 119 conjugation in cyclo-octatetra• 3,4-Dihydroxybenzoic acid, inac• ene,297,298 tivity of, in vitamin K2 biosyn• Franck-Condon effect in, 307 thesis, 164 influence of bond-alternation, 2,4 -Dihydroxy - 5,6 -dimethylbenzoic 305-9 acid, in aurantiogliocladin bio• Eleodes longicollis, benzoquinone bio• synthesis, II 0 synthesis in, 112 in flavipin biosynthesis, 91 Emodin, 180 incorporation into, 84 lloc,15 - Dihydroxy - 9 -ketoprost - 5- Enamines, in synthesis of bicyclic enoic acid, biosynthesis of, 179 compounds, 203-5,238 1,8-Dihydroxynaphthalene, in phenol -lactones, in synthesis of bicyclic coupling reactions, 119 compounds,209-10 1,3-Dihydroxy-2-propanone phos- Ergochrome AB, biosynthesis of, 97 phate, in biosyn• Ergosterol, biosynthesis of, 170 thesis, 132 Ergot, ergo chrome biosynthesis in, 97, 3,6 -Dihydroxy -2,5 -toluquinone, bio• 198a synthesis of, III D-Erythrose 4-phosphate, in shikimic Dimethylacetothetin, methylations acid biosynthesis, 132 by,85 Escherichia coli, mutants of, in studies 3,3-Dimethylallyl diphenyl phos• of biosynthesis, 128 ff phate, alkylation of phenols, by vitamin K2 biosynthesis in, 164 161 Ethionine, suppression of tropolone Dimethylallyl pyrophosphate, in ter• biosynthesis by, 105 pene and steroid biosynthesis, 2-Ethylbenzoquinone, biosynthesis of, 158,159 112 in humulone biosynthesis, 159 Ethyl diazoacetate, ring expansion 2,2-Dimethylchroman, formation of, with,106 161 Eucalyptus species, polyketide bio• Dimethyl xanthophanic enol, base synthesis in, 108 catalysed cyclisation of, 126 Euglena gracilis, terpenoid benzo• Diterpenes, biosynthesis of, 159 quinone biosynthesis in, 164 Dryopteris marginalis, margaspidin Evernia vulpina, vulpinic acid bio• biosynthesis in, 89 synthesis in, 147 Dryopteris species, methylenebisphlo• roglucinol biosynthesis in, 87 Farnesyl diphenyl phosphate, alky• Duclauxin, biosynthesis of, 91 lation by, 161 Farnesyl pyrophosphate, in cannabis constituent biosynthesis, 159 5,8, ll, 14, 17 -Eicosapentaenoic acid, in terpene biosynthesis, 159 in prostaglandin biosynthesis, Fatty acids, biosynthesis of, 78 ff, 126 178 Feist's acid, 249 ff 5, 8, 11, 14 - Eicosatetraenoic acid, see bond-lengths, 256 arachidonic acid, 176 derivatives, 255 8,1l,14-Eicosatrienoic acid, in pros• dibromo-, 261 taglandin biosynthesis, 178 preparation, 253 366 INDEX Feist's acid-cont. Gliocladium roseum, aurantiogliocla• reactions of, 257 ff din biosynthesis in, no related compounds, 266 D-Glucose, in spectra, 256 biosynthesis, 128 ff Fermi resonance, 218 in gallic acid biosynthesis, 144 Ferriprotoporphyrin IX, prosthetic in myo-inositol biosynthesis, 180 group in chloroperoxidase, 175 in L-viburnitol biosynthesis, 183 Ferulic acid, from sinapic acid, 145 Glucose 6-phosphate, in myo-inositol Flavanone-chalcone interconversion, biosynthesis, 180 67 trans - 2 - Glucosyloxy - 4 - methoxy• Flavesone, biosynthesis of, 109 cinnamic acid, in herniarin bio• Flavipin, biosynthesis of, 90, 91 synthesis, 138 Flavonoids, biosynthesis of, 148 ff Glucuronic acid, biosynthesis of, from Formononetin, biosynthesis of, 74 myo-inositol, 183 Fructose 1,6-diphosphate, in shikimic Glutamine, in formation of anthranilic acid biosynthesis, 132 acid from , 134 Fumigatin, biosynthesis of, III Gossypol, biosynthesis of, 119 Furanocoumarins, biosynthesis of, Grandiflorone, biosynthesis of, 109 140 Griseofulvin, biosynthesis of, 94-7 Furan ring, formation of in furano• polyketide nature of, 77 coumarins, 140 synthesis of, 96, 97 Gymnosperm lignin, structure of, 142 Gallic acid, biosynthesis of, 144-5 Gaultheria procumbens, benzoic acid Heat of formation and aromaticity, of biosynthesis in, 142 [18]annulene, 309 General acid catalysis of benzidine of biphenylene, 321-3 rearrangements, 13 of cyclo-octatetraene, 296, 297 Gentisaldehyde, in patulin biosyn• D-altro-Heptulose 1,7 -diphosphate, in thesis, 121 shikimic acid and aromatic amino Gentisic acid, biosynthesis of, 142 acid biosynthesis, 130 ff Geodin, formation from dihydrogeo• Hibiscus syriacus, cyclopropene fatty din of, 96 acid biosynthesis in, 170 conversion into geodin hydrate, 96 Herniarin, biosynthesis of, 138 Geodin hydrate, conversion into geo• Homo-y-linolenic acid, see 8,11,14- doxin of, 96, 139 eicosatrienoic acid, 178 formation from geodin of, 96 Hop constituents, biosynthesis of, 159 Geodoxin, formation from geodin Hordeum species, aromatic acid bio- hydrate of, 96, 139 synthesis in, 145 Geranium pyrenaicum, gallic acid Huckel's rule, 270-2 biosynthesis in, 144 Humulone, biosynthesis of, 159 Geranyl pyrophosphate, in terpene Hydrangea species, hydrangenol bio- biosynthesis, 159 synthesis in, 156 Geranylgeranylpyrophosphate, in ter- Hydrangenol, biosynthesis of, 156 pene biosynthesis, 159 Hydrazoarenes, basicity, 8 Gibberellafujikuroi,70 disproportionation by acids, 52 Gibberellins, 70 disproportionation by bases, 56 Glaucanic acid, biosynthesis of, 184-8 disproportionation by heat, 50 Glauconic acid, biosynthesis of, 184-8 disproportionation by u.v.light, 50 INDEX 367 Hydride transfer in bicyclononanes, Illicium dnisatum (I. religiosum), 226-7 shikimic acid in, 128 Hydroquinone glucoside, see Arbutin Impatiens balsamina, 2-hydroxy-l,4- 3-Hydroxyanthranilic acid, and 0- naphthaquinone biosynthesis in, pyrocatechuic acid biosynthesis, 166 145 Infra-red spectra of bicyclononanes, p-Hydroxybenzoic acid, biosynthesis 216, 218-21 of,142 CO doublets, 218-21 from caffeic acid, formation of, 145 D-Inositol, biosynthesis of, 180, 182 in arbutin biosynthesis, 146 L-Inositol, biosynthesis of, 182 in ubiquinone biosynthesis, 162-4 meso-Inositol, see myo-Inositol nutritional requirement of E. coli myo-Inositol, biosynthesis of, 180-2 mutants for, 128 in apiose biosynthesis, 183 m-Hydroxybenzyl alcohol, in patulin in biosynthesis of cell-wall poly• biosynthesis, 121 saccharides, 183, 198b p-Hydroxycinnamic acid, in flavonoid myo-Inositol I-phosphate, intermedi• biosynthesis, 148, 149 ate in myo-inositol biosynthesis, p-Hydroxy-trans-cinnamic acid, for• 182 mation from , 136 f3-Ionone, 208 p -Hydroxy -cis-cinnamic acid, in novo• Iridoskyrin, biosynthesis of, 120 biocin biosynthesis, 139 Islandicin, biosynthesis of, 83 p-Hydroxycinnamyl alcohol, in lignin 180 incorporation into, 84 formation, 142 relationship to iridoskyrin of, p-Hydroxycinnamyl-CoA, in flavo• 120 noid biosynthesis, 150 Isobutyryl-CoA, in tasmanone bio• 11 CI. - Hydroxy - 9, 15 - diketoprost - 5 - synthesis, 108 enoic acid, biosynthesis of, 179 in grandifiorone biosynthesis, 109 5-Hydroxyisophthalic acid, degra• Isoclovene, 214 dation of stipitatic acid to, 105 Isoflavones, biosynthesis of, 73-5 150, Hydroxylation, of aromatic sub• 151, 198c strates, 143-6 L-Isoleucine, as precursor of branched (S) - 4' - Hydroxy - 4 - methoxydalber• chain fatty acids, 107 gione, 154 Isopentenyl pyrophosphate, in ter• CI. - Hydroxymethylserine, formation pene and steroid biosynthesis, of, 189 157, 158, 159 2 - Hydroxy - 1, 4 - naphthaquinone Isoprenylcoumarins, occurrence in (lawsone), biosynthesis of, 166 plants, 140 p-Hydroxyphenylpyruvic acid, for• Isoprenylnaphthaquinones, occur- mation from prephenic acid of, rence of, 167 134 Isopropylfuranocoumarins, occur- inactivity of, in vitamin K2 bio• rence in plants, 140 synthesis, 164 Isotope effects in benzidine rear• 3-Hydroxyphthalic acid, biosyn• rangements, kinetic, 16,46,48 thesis of, 83 product, 27 4-Hydroxypretetramid, in tetracy• solvent, 16 cline biosynthesis, 113 Isovaleryl-CoA, in humulone biosyn• 3-Hydroxy-2,5-toluquinone, biosyn• thesis, 159 thesis of, III in leptospermone biosynthesis, 109 368 INDEX Jahn-Teller effect, definition, 276 Mammea americana, constituents of, examples, 277 155 in annulenes, 278-82 Margaspidin, biosynthesis of, 90 in cyclo-octatetraene derivatives, Membrane permeability, 72 302,303 Metal ions, in secondard metabolism, J avanicin, biosynthesis of, 98, 99, 115, 189 166 Methionine, as methyl donor, 84 in barnol biosynthesis, 86 Kaempferol, in isoflavone biosyn• in duclauxin biosynthesis, 91 thesis, 73, 74 in flavipin biosynthesis, 91 ,8-Ketoadipicic acid, in caldariomycin in lactobacillic acid biosynthesis, biosynthesis, 174 170 16-Ketoprogesterone, enzymatic hal• mechanism of methylation by, 171, ogenation of, 175 172 in methylenebisphloroglucinol bio• Lactobacillus arabino8U8, lactobacillic synthesis, 87, 89 acid biosynthesis in, 170 in mycophenolic acid biosynthesis, Lavandula oificinalis, coumarin bio• 86 synthesis in, 138 in tasmanone biosynthesis, 108 Lawsone, see 2-hydroxy-l,4-naphtha- in vitamin K2 biosynthesis, 165 quinone, 166 Methionine sulphoxide, 173 Leptospermone, biosynthesis of, 109 Methylaspidinol, in p-aspidin biosyn• L-Leucanthemitol, 180 thesis, 87 Leucine, in humulone biosynthesis, formation of methylene-bisaspidi• 159 nolfrom,88 Lignin, 140 ff Methylation, biological, mechanism Lucerne, coumestrol biosynthesis in, of, 170-3 152 a-Methylbutyryl-CoA, in branched Lycopodine, synthesis, 213 chain fatty acid biosynthesis, 107 Lysine, in l-amino-2-nitrocyclopen• 3-Methyl-6-8-dihydroxyisocoumarin, tane carboxylic acid, biosyn• synthesis of, 124 thesis, 173, 189 Methylenebisphloroglucinol, biosyn• thesis of, 127 Machaerium scleroxylon, neoflavo• Methylenecyclopropane - trans - 1, 2 - noids in, 154 dicarboxylic acid, see Feist's acid Macrolides, biosynthesis of, 109 D <+)-14-methylhexadecanoic acid, Magnetic susceptibility, see Suscepti• biosynthesis of, 107 bility Methylmalonic acid-succinic acid Maize, terpenoid biosynthesis in, 72 interconversion, 107 Malonamyl-CoA, possible role in tetra• Methylmalonyl-CoA, in macrolide bio• cycline biosynthesis, 115 synthesis, 109 Malonyl-CoA, in branched-chain acid 2-Methyl-l,4-naphthaquinone, in vit• biosynthesis, 107 amin K2 biosynthesis, 165 in fatty acid biosynthesis, 79 Methylphloracetophenone, biosyn• in flavonoid biosynthesis, 148, 149 thesis of usnic acid from, 117 in polyketide biosynthesis, 83 enzymatic conversion into usnic in tetracycline biosynthesis, 115 acid hydrate of, 118 Malvalic acid, biosynthesis of, 170 synthesis of usnic acid from, 116 INDEX 369 6-Methylsalicylic acid, in terreic acid Neurospora cra8sa,..-..-cont. biosynthesis, 113 formation of protocatechuic acid biosynthesis of, 126 from 5-dehydroshikimic acid in, in patulin biosynthesis, 121 134 Methyl sulphonium cation, 173 Nicotinamide adenine dinucleotide, in D (+)-12-Methyltetradecanoic acid, biosynthesis of 5-dehydroquinic biosynthesis of, 107 acid,133 Methyl triaceticlactone, occurrence in in biosynthesis ofp-hydroxyphenyl• P. stipitatum of, 105 , 134 utilisation in tropolone biosynthesis possible role in barnol biosynthesis, of, 106, 198a 86 Methymycin, biosynthesis of, 109 ,B-Nitropropionic acid, biosynthesis of, Mevalonic acid, 72 173 III anthraquinone biosynthesis, Nonadrides, biosynthesis of, 184-8 167-9 , biosynthesis of, 138 in terpene biosynthesis, 157 Nuclear magnetic resonance spectra, in ubiquinone biosynthesis, 163 of [l8]annulene and derivatives, Mexicanolide, 234 310-13 Michael addition, in p-aspidin biosyn• of [24]annulene, 315 thesis, 87 of bicyclononanes, 222-3 in secondary metabolism, 188 of biphenylene and deuterated deri. Model reactions, ofpolyketide biosyn- vatives, 328-34 thesis, 123 of I,ll - bisdehydro[20]annulene, Molar susceptibility, definition, 282 346, 347 Monascorubin, biosynthesis of, 102 of cyclo-octatetraene and deriva• Monascus purpureus, polyketide bio- tives, 298-302 synthesis in, 100 ff Monoterpenes, biosynthesis of, 159 Oleic acid, polyacetylene formation Mycobacterium phlei, vitamin Kl bio• from, 102 synthesis in, 165 Olivetol carboxylic acid, synthesis of, Mycobacterium smegmatis, tuberculo• 125 stearic acid, biosynthesis in, 170 Orcinol, alkylation of, 161 methylation in, 171 from diacetylacetone, 77 Mycobacterium tuberculosis, phthie• Orsellinic acid, formation from tetra• noic acid biosynthesis in, 109 cetic lactone of, 127 Mycophenolic acid, biosynthesis of, in aurantiogliocladin biosynthesis, 86 110 in flavipin biosynthesis, 91 in toluquinone biosynthesis, III Naphthapyrones, occurrence of, 167 lack of incorporation into terreic 1,4-Naphthaquinone, in alizarin bio• acid of, 113 synthesis, 167 possible role in tropolone biosyn• Naphthaquinones, biosynthesis of, thesis of, 104 164-6, 198b synthesis from triacetic acid of, 124 Naphthocyclobutadienes and related Oryza species, aromatic acid biosyn• compounds, 317-19 thesis in, 145 Neurospora crassa, ergosterol biosyn• Oxaloacetate, intermediate in non• thesis in, 170 adride biosynthesis, 186 370 INDEX Oxidative cleavage, of aromatic com• Peroxide, intermediate in prostaglan• pounds, 120 ff din biosynthesis, 179 Oxygen-18, in incorporation studies, Pertusaria amara, picrolichenic acid 68,84,179 from, 119 Oxytetracycline, biosynthesis of, 113 Phenol coupling reactions, 66, 115 ff Phenonium ion, intermediate in iso• flavone biosynthesis, 151 Palmitic acid, biosynthesis of, 80 Phenoxonium ion, intermediate in Patchouli alcohol, 232-3 novobiocin biosynthesis, 139 Pelargonium hortorum, gallic acid , biosynthesis of, 128 biosynthesis in, 145 formation of trans-cinnamic acid Penicillic acid, biosynthesis of, 120 from, 136 Penicillium aurantio-virens, tropo• in benzoquinone biosynthesis, 112 lones of, 104 in calophyllolide biosynthesis, 155 Penicillium barnense, barnol biosyn• in gallic acid biosynthesis, 144 thesis in, 86 in isoflavone biosynthesis, 73, 74 penicillic acid biosynthesis in, 121 in ubiquinone biosynthesis, 163 Penicillium brevi-compactum, myco• in volucrisporin biosynthesis, 146 phenolic acid biosynthesis in, 86 in vulpinic acid biosynthesis, 147 Penicillium cyclopodium, tropolones DL-Phenyl-lactic acid, in volucrisporin of,104 biosynthesis, 146 Penicillium duclauxi, duclauxin bio• Phenylalanine deaminase, 137 synthesis in, 91 4-Phenylcoumarins, biosynthesis of, Penicillium estinogenum, geodin for• 154 mation in, 96 Phenylpyruvic acid, formation from Penicillium glaucum, nonadrides in, prephenic acid of, 134 184 inactivity of, in vitamin K2 bio• Penicillium islandicum, emodin bio• synthesis, 164 synthesis in, 84 in volucrisporin biosynthesis, 146 islandicin biosynthesis in, 84 DL-Phenylserine, in volucrisporin bio• phenol coupling reactions in, 120 synthesis, 146 Penicillium notatum, xanthocillin bio• Phloracetophenone, lack of incor• synthesis in, 147 poration into usnic acid of, 118 Penicillium patulum, griseofulvin bio• Phosphoenolpyruvate, in shikimic synthesis in, 96 acid biosynthesis, 132 patulin biosynthesis in, 121 4'-Phosphopantotheine,80 Penicillium purpurogenum, nonadride Phthienoic acids, biosynthesis of, 109 biosynthesis in, 184 Phycomyces blakesleeanus, gallic acid Penicillium sclerotiorum, sclerotiorin biosynthesis in, 144 biosynthesis in, 170 Phylloquinone (vitamin Kl), biosyn- Penicillium stipitatum, tropolone bio• thesis of, 164 synthesis in, 104 Phytosterols, biosynthesis of, 172 Penicillium urticae, biosynthesis of 6- Picrolichenic acid, biosynthesis of, 119 methyisalicylic acid in, 83 Pimpinella magna, furanocoumarin griseofulvin biosynthesis in, 97 biosynthesis in, 140 Peroxidase, in methylenebisphloro• Pinosylvin, biosynthesis of, 156 glucinol biosynthesis, 88 Pipitzols, 229 phenol coupling by, 118 Pisatin, biosynthesis of, 152 INDEX 371 Plastoquinone, biosynthesis of, 161-4 Pyrophosphate, as leaving group in Polyacetylenes, biosynthesis of, 102 ff terpene biosynthesis, 158 Polyenes, 7T-energy of, 273, 274 Pyrromycin, biosynthesis of, 11 0 Polyketide biosynthesis, enzymology €-Pyrromycinone, biosynthesis of, 110 of, 126 ff Quercetin 73,74 Poly-f3-keto derivatives, 66 L(+)-Quercitol, 180 Polymerisation of cinnamyl alcohols, biosynthesis of, 182 in lignin formation, 142 Quinic acid, in aromatic amino acid Polyporic acid, ring cleavage of, 146, biosynthesis, 128 147 Quinone methide, intermediate in Polypyrones, synthesis and base cata• barnol biosynthesis, 86 lysed condensations of, 124 intermediate in p-aspidin biosyn• Prephenic acid, in aromatic amino thesis, 87 acid biosynthesis, 130, 134 Primary metabolites, 69 ff Radicals in benzidine rearrangements, Primula acaulis, benzoic acid biosyn• 5,40,45 thesis in, 142 Rearrangements, benzidine, 1 ff Prostaglandins, the, 175-80 bicyclononanes, 202, 214-15, 232 PGEl 176, 178, 179 caryophyllene, 214, 215 PGE z176 Feist's acid, 262-4 PGEa 176, 178 Red Cabbage, biosynthesis PGFl 176, 179 oc in, 150 PGFzoc 176, 179 f3-Resorcylic acids, synthesis of, 125 PGFaoc 176 Rhodospirillum 1'ubrum, ubiquinone Protocatechuic acid, biosynthesis of, biosynthesis in, 163 142 Rhus typhina, gallic acid biosynthesis formation from 5-dehydroshikimic in, 144 acid of, 134 Ring-currents, in benzenoid aromatic in caldariomycin biosynthesis, 174 hydrocarbons, 285 in gallic acid biosynthesis, 145 criterion of aromaticity, 287, 289 Proton chemical shifts, in benzenoid definition, 283 aromatic hydrocarbons, 285 influence of bond-alternation upon, calculation of, 286 288 influence of bond-alternation upon, paramagnetic, 286 288 Robinson annelation reaction, 206-7 Pseudoclovenes, 214 Rotenone, biosynthesis of, 152 Pseudopurpurin, biosynthesis of, Rotiorin, biosynthesis of, 100, 127 168-9 Rubia tinctorum, anthraquinone bio- Puberulic acid, biosynthesis of, 104 synthesis in, 167 Puberulonic acid, biosynthesis of, 104 Rubropunctatin, biosynthesis of, 102 Pulvic acid, biosynthesis of, 146 Rutilantins, biosynthesis of, 110 Pulvic dilactone, biosynthesis of, 146 Pummerer's ketone, enzymatic syn- thesis of, 118 Salicylic acid, and o-pyrocatechuic formation of, 116 acid biosynthesis, 145 Purpurin, biosynthesis of, 167 biosynthesis of, 142 o-Pyrocatechuic acid, biosynthesis of, Salt effects in benzidine rearrange• 142 ments,17 372 INDEX Sclerotiorin, biosynthesis of, 100, 127, Streptomyces venezuelae, methymycin 170 biosynthesis in, 109 Scleroin, biosynthesis of, 154 Succinic acid-methylmalonic acid in• Scyllitol, biosynthesis of, 297 terconversion 107 Secondary metabolites, 69 ff Succinic acid, in glauconic acid bio- p-Sernidine formation in benzidine synthesis, 186 rearrangements, 44 Sulochrin, biosynthesis of, 94 ff, 198a Sequoyitol,180 Sulphonium ylides, 172-3 Sesquiterpenes, biosynthesis of, 159 Susceptibility exaltation, [16]annu- Shikimic acid, 70, 128 ff lene, 316 in anthraquinone biosynthesis, 167 benzenoid aromatic hydrocarbons, in caldariomycin biosynthesis, 173 284 in 2-hydroxy-l,4-naphthaquinone cyclo-octatetraene, 297 biosynthesis, 166 definition, 282 in ubiquinone biosynthesis, 163 Swietenine, 217, 234-6 in vitamin Kl biosynthesis, 164 Syringic acid, biosynthesis of, 142 in vitamin K2 biosynthesis, 164 in volucrisporin biosynthesis, 146 Tasmanone, biosynthesis of, 108 possible role in tropolone biosyn- Taxifolin, biosynthesis of, 151 thesis of, 105 Terpene biosynthesis, 157 ff Sinapic acid, demethoxylation of, 145 Terphenyl derivatives, biosynthesis Sinapis alba, myo-inositol biosynthesis of,146-8 in,180 Terreic acid, biosynthesis of, 112 Sinapyl alcohol, in lignin formation, Terrein, biosynthesis of, 120 142 Tetra-acetic lactone, in orsellinic acid IX-Smegmamycolic acid, biosynthesis biosynthesis, 127 of,l71 occurrence in P _ stipitum of, 105 Skytanthus, alkaloid biosynthesis in, utilisation in tropolone biosyn• 169 thesis, of 106 Solvent effects on acid-catalysed ben• Tetracyclines, biosynthesis of, 71, zidine rearrangements, 16, 17 113ff Solvent effects on thermal benzidine Tetrahydroxybenzoquinone, biosyn• rearrangements, 46 thesis of, 184 Specific acid catalysis of benzidine 4,5,4',5' -Tetrahydroxy-l, I' -binaph- rearrangements, 13 thyl, biosynthesis of, 119 Spinulosin, biosynthesis of, 111 Tetranortriterpenoids, 234 Sterculic acid, biosynthesis of, 170, Thioesters, condensations of, 65 198b IX-Tocopherolquinone, biosynthesis of, Stilbenes, biosynthesis of, 156 161-4 Stipitatic acid, biosynthesis of, 104 ff, Tocopherols, biosynthesis of, 161-4 198a Tocotrienols, biosynthesis of, 161-4 laboratory synthesis of, 106 Toluquinol, in patulin biosynthesis, Stipitatonic acid, biosynthesis of, 121 104 Toluquinone, biosynthesis of, 112 Streptomyces mutants, tetracycline Transport phenomena, 72 biosynthesis in, 113 Triacetic acid, 124 Streptomyces niveus, novobiocin bio• Triacetic lactone, occurrence in P. synthesis in, 138 stipitatum of, 105 INDEX 373 Triacetic lactone-cont. Vanillic acid, biosynthesis of, 142 utilisation in tropolone biosyn• from sinapic acid, 145 thesis of, 106 Violastyrene, 154 1,3,4-Trimethoxybenzene, in stipi• Vitamin Kl (phylloquinone) biosyn• tatic acid synthesis, 106 thesis of, 164 Triticum vulgare, aromatic acid bio• Vitamin K2 (menaquinone), biosyn• synthesis in, 145 thesis of, 164, 165 Tropolones, fungal, biosynthesis of, Vitamin K2 (45) H, biosynthesis of, 104 ff 171 Tryptophan, biosynthesis of, 128, 134 Volucrispora aurantiaca, volucrispo• Tuberculostearic acid, biosynthesis of, rin biosynthesis in, 146 170 Vulpinic acid, biosynthesis of, 146 Tyrosine, biosynthesis of, 128 formation of p-hydroxy.trans.cin• namic acid from, 136 Wichterle reaction, 205 in novobiocin biosynthesis, 138 in terpenoid benzoquinone biosyn• thesis, 164 in ubiquinone biosynthesis, 163 Xanthocillin, biosynthesis of, 147 in xanthocillin biosynthesis, 147 X-ray analysis of structure, [14Jan- Tyrosine deaminase, 137 nulene, 313 [16Jannulene, 358 Ubiquinones, biosynthesis of, 161-4 [l8Jannulene, 305, 358 Umbelliferone, biosynthesis of, 138 bicyc1ononanes, 216 Usnic acid, biosynthesis of, 116 biphenylene, 320 synthesis of, 116 1,4-bisdehydro[14Jannulene, 343, Usnic acid hydrate, enzymatic for• 344 mation of, 118 cyclo-octatetraene, 296 Feist's acid, 256 Vaccenic acid, in lactobacillic acid tetraphenylene, 336 biosynthesis, 170 Valine, isobutyryl-CoA formation from, 108 Yeast, fatty acid synthetase of, 80