Index

Acetaminophen Aminoethanc sulfate, 295 , 426 2-Amino-3-hydroxyacetophenone-0- poisoning, 212 sulfonate, 300 sulfate excretion, 300 Anchimeric assistance, 272-273 sulfonation, 299 Androsterone, 317 N-Acetyi-N-hydroxy-2-aminofluorene Aniline, 308 carcinogenicity, 346 Antithrombin Ill, 338 metabolism, 345-347 Araneus, 173 mutagenicity, 346 Ar~:iopes, 173 N-Acctyi-N-hydroxy-2- Aryl (E.C .2.8.2.1.) aminophenanthrene, 347 distribution, 304-305 Acetylthiokinase (E.C. 6.2.1.1 ), 229-230 isozymes, 430 .. Active aldehyde" separation, 305 nucleophilicity, 278 types, 301-302 from thiamine, 277 Aryl (E.C.3.1.6.1) thioester formation, 256 activities, 309, 312 Adenosine phosphosulfate types, 309 formation, 20, 21 , 309 oxidation, 25 , 309 reduction, 22 Arylsulfatase C, 312 structure, 19 Ascophyllum, 341 Adenosine phosphosulfate reductase Ascorbate 2-sulfate (E.C.I.8.99.2), 19, 21 arylsulfatase A, 313 Adenosylcobalamin, 365 distribution, 319 Adenosylhomocysteinase (E.C.3.3.1.1 ), 63 hydrolysis, 297, 309 s-Adenosylhomocysteine Aspartate aminotransferase (E.C.2.6.1.1) adenosylmethionine inhibitor, 63 inhibition by serine 0-sulfate, 130 metabolism, 63 metabolism of CSA, 129 methylase inhibitor, 78 Assimilatory reduction, II S-Adenosylmethionine decarboxylase Asterubin, 172 (E.C.4.1.1.50), 82 ATP sulfurylase (E.C.2.7.7.4), 21 Agar Autotrophism, 12 industrial use, 341 Avidin, 282 structure, 344 Azaserine, 249 Aging, 5 Alanine sulfate, 295 Bacteriochlorophyll, 15 Alcohol dehydrogenase (E.C.I.I.I.I ), 211 Basement membrane, 340 Allicin, 209-210 Basic amino aciduria, 379

437 438 Index

Beriberi. 279-280 Cholesterol sulfate Bile salt (E.C.2.8.1.14), functions, 316 307 in sperm membranes, 385 Bile sulfates. 318 in sulfate deficiency. 385 Biotin Cholestyramine , 280-284 effect on bile composition, 167 biosynthesis, 88 taurine depletion, 148 fatty acid synthesis. 232 Choline 0-sulfate, in plants, 319 oxidation. 273 Chondroitin 4-sulfate. arylsulfatase B, 309 reactivity. 3 Chondm.1·, 341 Bufothionine, 304 Chromate. 27 Buthionine sulfoximine. GSH depletor. Citrate (E.C.4.1.3.6), 244 374. 421 Citrate synthase (E.C.4.1.3.7). 232 Butter yellow, 295 Clavulanic acid, 288 Cleland's reagent, 218 Caerulein Clindamycin, 273 source, 325 Cobalamin deficiency. 365 sulfonation. 308, 325 Calcium paradox. 157 ;-'!alogs, 230 S-Carboxycysteine. 250 discovery. 199 S-Carboxymethylthiocysteine. 176 Collagen Cardiomyopathic hamster, 157 cystathionine ,8-synthase deficiency, 370 Carnitine acyltransferase (E.C.2.3.1.7). 235 intracellular space. 330 Carotenoid, 15 proteoglycans. 336 Carrageenan. 341-344 types, 336 Cartilage. structure. 335-337 Conditional essentiality. 150 Cation-binding, 3 Congestive heart failure, 161 Cephalosporin C. isolation. 286 Corticosteroid sulfotransferase. 307 Cephalosporins Corticosterone reduction. 318 biosynthesis, 286-287 Creatine, 66 as thioethers, 271 Cyanolysis, of , 220 Cephamycins, 286 Cystaldimine formation, 138 Cerebellar neurons. in taurine deficiency, Cystamine 151 inhibition of y-glutamylcysteine Cerebroside sulfate synthase, 246 arylsulfatase A. 309 radioprotectant, 217 metabolism. 322 f:l-Cystathionase (E.C .4.4.1.8) opiate receptor. 323 in enteric bacteria. 35 Cerebroside 3-sulfate, Na/K-ATPase. 323 GSH synthesis, 246 Charonan. 344 in methionine biosynthesis. 37-38. 42 Chemotrophism. 12 y-Cystathionase ( E.C .4.4.1.1) Chinese restaurant syndrome. 123 absence in microorganisms, 32 Chitin, 339 catalytic activities, 179 Chitosan. anticoagulant activity. 339 cystine cleavage, 211 Chloramines, 173 fetal, 94 Chlorobactenc. 15 in transsulfuration, 93 f:l-Chloroethyl sulfide. 2 Cystathionine metabolism. 35-36 Cholecystokinin Cystathionine ,8-synthasc (E.C.4.2.1.22) sulfonation. 325 absence in microorganisms. 32 sulfotransferasc acting on. 305 subunit structure, 368 Index 439

Cystathionine {3-synthase (E.C.4.2.1.22) Cystine reductase (E.C.I.6.4.1), 219 (cont.) Cystinosis in transsulfuration. 93 forms, 380 Cystathionine y-synthase (E.C.4.2.99.9). in glomerular damage, 381 Neurospora. 43 retinal depigmentation, 381 Cystathioninuria. metabolic causes. 364 Cystinuria Cysteamine in Libyan Jews. 380 in coenzyme A. 224 in Swedes, 379 ionization, 201 Cytochrome C., 20-21 metabolism. 136 Cytochrome P-450 monooxygenases. 413 oxidation, 138 radioprotectant. 138. 217 De'Toni-Debre-Franconi syndrome, 380 treatment of cystinosis, 381 Decanoylsarcosyltaurine, 163 Cysteamine derivatives. 230 Dehydroepiandrosterone sulfate. 385 Cysteamine dioxygenase Dehydroepiandrosterone sulfate sulfatase, distribution, 129 384 enzymology, 138 Deoxycorticosterone 21-sulfate reduction, 318 biosynthesis, 34 Dermatan sulfate catabolism, 392 inhibition of aspartate aminotransferase. Desulforubidin, 23 124 De.w!fiJtomaculum. II ionization. 201-202 Desu!fiwihrio, II, 20 neurotoxicity. 123 Desulfoviridin, 22, 23 oxidation. 121 1,9-Diamino-5-azanonane, 85 pK". 201 2,3-Dibromobenzyl alcohol disulfate, 294, regulation. 34 304 source of sulfane, 124 Dibromopropanone, 243 tissue concentrations, 123 1,2-Dichloroethane, metabolic activation, transamination versus decarboxylation. 427-428 121-122 Diethyl maleate Cysteine aminotransferase (E.C.2.6.1.3). formaldehyde metabolism, 427 124 GSH depletion, 421 . 129 Difluoromethyl ornithine. 81 Cysteine sulfinic acid Dimethyl cyclothiabutane, in mink. 269 formation, 129 Dimethyl sulfide, 98 metabolism. 129, 132 Dimethylguanidinoethane sulfonate, 172 neuroexcitant. 129 Discadenine. 88 regulation of excitability. 132 Dissimilatory reduction, II Cysteine sulfinic acid decarboxylase , 2 (E.C.4.1.1.29) Disulfide exchange, 217-218 distribution. 134 Dithiomethylmethane, in truffles, 269 specificity, 132 Dithionate, 20 D-Cysteinolic acid. 173 1,4-Dithiothreitol, 218 Cysteinyi-DOPA. 180 Djenkolic acid. 271 Cystine Dopamine sulfonation, 314 cystathionase, 211 reduction, 176 Ectopis lentis. 369 solubility, 379 Endothelial cells, glycosaminoglycans, 333 transpeptidase substrate, 249 Endothelium. heparin. 338 transport systems. 378 Enkephalin. 305 440 Index

Epilepsy, taurine. 153 Glutathione (cont.) Epimer, definition, 30 free radical scavenger, 417, 422 Epimeric pairs, in glycosaminoglycans, 330 metabolism of formaldehyde, 4 I 7 Epinephrine sulfate, 315 nucleophilic properties, 4 I 5 Epsom salts, absorption. 299 oxidation by chloramine, 173 Ergothioneine, 199 pK,, 201 17 f:l-, sulfonation, 317 reaction with aldehydes, 213 Estriol 3-sulfate, 300 reaction with formaldehyde, 426 , sulfonation, 305. 317 reaction with f:l-propiolactone, 214 , 300 redox potential, 415 Estrone sulfate sulfatase, 384 reduction of homocystine, 218 , 307 xenobiotic metabolism, 415 Ethylene, 86-87 Glutathione peroxidase (E.C. !.1 I. 1.9), 25 I, N-Ethyl male imide 423-426 mechanism of reaction with SH, 212 (E. C. I .6.4.2) S-adenosylmethione decarboxylase, 82 , 219 Eumelanins, I 79-I 80 maintenance of redox state, 250 Glutathione (E.C.2.5. I. 18) Fava beans, hemolytic anemia, 425 conjugation reactions, 417-422 Ferredoxins distribution, 420-42 I in APS pathway, 31 forms, 418 redox potential, 24 nomenclature, 418 reduction, 2 I phase II , 414 content. 2 in redox system, 25 I Fibrinopeptide B Glutathione transhydrogenase, see function, 325 Glutathione transferase sulfonation, 308 Glutathionemia, 377 Fibroblasts, in methylene THF reductase Glutathionuria, 377 deficiency, 365 Glycosaminoglycans Flavanoid sulfates. in plants, 319 arteries, 333 Flavodoxin, 21 calcium binding, 333 Flavoprotein, 19 catabolism, 387 Formaldehyde metabolism, 426 formation of proteoglycans, 333 Fucan sulfate, 344 post-translational modifications, 332 "stiff finger" conformation, 333, 336 structural variability, 332 Galactans. 344 Glyoxylase I (E.C.4.4.1.5), 252 Gastrins, sulfonation, 308, 325 Glyoxylase II (E.C.3. I .2.6), 252 Gelidum, 341 Gramicidin, 244 Glucuronidation Greene, Graham, The Third Man, 286 hydroxamates, 345 Ground substance, glycosaminoglycans, versus sulfonation, 297 327 Glutamate decarboxylase (E.C.4. I. I. 15), Guanidinoethane sulfonate, 171-172 substrate specificity. 132 -y-Giutamyl transpeptidase, inhibitors. 249 -y-Giutamyltaurine, 170 Hagfish. 164 Glutathione Harmol, 300 in assimilatory reduction, 30 , catabolism, 393 biochemistry, 245-252 Heterotrophism, 12 as cofactor, 3 Hexachloro- I ,3-butadiene, metabolic demethylation reactions, 427 activation. 428 Index 441

Homocysteic acid, 367 Insulin (cont.) Homocysteine stimulation of phospholipid metabolism, 64, 66 methyltransferase, 78 methylation, 74 Intestinal mucosa. source of heparin, 339 in plasma, 364 lodoacetate, 212 Homocysteine sulfinic acid, 367 -sulfur proteins, 3 Homocysteinemia, 72 lsethionic acid, 135 Homocystinuria, causes, 361 lsorenieratene, 15 Homolanthionine. 367-368 lsothiocyanates. from glucosinolates, 349 Homoserine lactone. 86-87 Hunter syndrome metabolic cause, 393 Kahweofuran. 200, 270 X-linked. 391 Keratan sulfate, catabolism 392 Hurler-Scheie syndrome, 397 a-Keto-y-methylthiobutyrate. 98, 99 Hurler syndrome a-Ketoglutarate dehydrogenase defects in 396-397 (E.C.I.2.4.2). lipoic acid, 254 distinction from Hunter syndrome, 394 Killer rats, 153 Hyaluronic acid, collagen. 334 Hydrogen bonding. 7-8 Hydrogen peroxide metabolism, 250-251 Lampreys, 164 reduction. 250, 423 Lanthionine Hydrogen sulfide metabolism, 138 cytotoxicity. 38 oxidation. 273 flux in biosphere, 16-17 as thioether. 271 in oxidizing organisms, 15 Latimerol sulfate, 163 pK.,, 201 Lead, chemoshock thresholds, 150 in sulfureta, 18 Lenthionine. 4 Hydroperoxides, cytotoxicity. 423 Lincomycin, 273 N-Hydroxyacetaminophen, 347 Link protein, 334 8-Hydroxymercuribenzoate, 82 Lipoamide dehydrogenase, homology, 251 Hydroxynapthoquinone sulfate, 304 Lipoamide reductase (E.C.I.8.1.4). 219 N-Hydroxy-N-methyl-4-aminobenzene. 348 Lipoate acetyltransferase (E.C.2.3.1.12). Hydroxysteroid sulfotransferases 255 (E.C.2.8.2.2) isozymes, 430 Lipoate succinyltransferase (E.C.2.3.1.61), N-Hydroxyxanthine. 348 255 Hypermethioninemia, metabolic causes, Lipoic acid 364 biochemistry 252-256 Hypotaurine as cofactor. 3 distribution, 134 discovery, 199 in hepatectomy. 135 Lipoprotein lipase (E.C.3.1.1.34). metabolism, 135-137 endothelial 339 semen, 134 Lithotrophism, 12 sperm motility factor, 135 Litoralon, 170 Liver dysfunction, sulfonation. 318 Lowe's syndrome, 399 Ichthyosis, in sulfatase deficiency, 385 (E.C.I.I3.12.7), 257 lmerslund's syndrome. 361, 365 Luciferin sulfotransferase (E.C.2.8.2.10), lnotropy, and taurine. 157 308 Insulin Lysyl oxidase, cystathionine /3-synthase disulfide bridges, 219 deficiency. 370 442 Index

Magnesium sulfate, absorption, 299 Monobactams, 286, 288 Maroteau-Lamy syndrome Morquio syndromes metabolic cause, 394 metabolic causes, 396 urinary dermatan sulfate, 391 metabolic defect, 387 Marti us yellow, 295 urinary keratan sulfate, 391 Mast cells, heparin, 338 Mucopolysaccharidoses Megaloblastic anemia, 365 features, 391 Melarsoprol, 206 origins, 387 Menaquinones, 21 Multiple sulfatase deficiency, 398-399 Mercaptoacetate, 177 Myrosinase, 349 {:1-Mercaptoethanol, 225 Myxinol disulfate, 163 3-Mercaptolactate formation, 124 Napthol S yellow, 295 reaction with cysteine, 177 2-Napthylamine, 308 Mercaptopyruvate P-Nitrophenol, arylsulfotransferase (E.C.2.8.1.2), 124-125, 128 substrate, 305 Mercapturic acids P-Nitrophenyl sulfate, 297, 309 formation, 417 Nitrous oxide, 73 structure, 213 Norspermine, 85 Metachromatic leukodystrophy, 386-387 Nuphar alkaloids, 271 Methanethiol formation from methioine, 99 Olfactory bulb, 153 substrate for cystathioine-f:l-synthase, 38 Ommatin D, in insects, 304 Methanogens, 18 Orb-weaving spiders, 173 Methionase (E.C.4.4.1.11), 93 Organotrophism, 12 Methionine Ornithine, 79 discovery, 199 Ornithine decarboxylase (E.C.4.1.1.17), metabolic capacity, 372 81-83 metabolism, 65 Osteoporosis, cystathionine f:l-synthase plasma levels, 264 deficiency, 369 resynthesis from methylthioadenosine, f:l-Oxidation, 233, 235-236 91 Oxoproline, 247-248 sulfate balance, 301 2-0xothiazolidine-4-carboxylate, 250 toxicity, 98 Methionine adenosyltransferase, PAPS , 366 assimilatory reduction, 30-32 Methionine sulfoxide, 367 biosynthesis-mammals, 298-299 Methionine sulfoximine, inhibition of GSH structure, 19 synthesis, 246 sulfate activation, 28 Methyl group neogenesis, 65 sulfate donor, 29 Methyl orange, 295 sulfonation, 297 Methyl sulfide, 4 Paraquat, 250 3-Methyl thiopropionate, 99 Penicillamine Methyl viologen, 34 chelating agent, 206 N•-Methyladenine, 79 pKa, 201 5-Methylcytosine, 79 Penicillins Methylmalonyl CoA mutase biochemistry, 284-289 (E.C.5.4.99.2), 365 history, 284 Methylthioribose, 91 oxidation, 274 Molybdate, 27 pronunciation, 286 Index 443

Penicillins (mnt.) (E.C.2.8.1.1) (cont.) as thioethers, 271 reaction mechanism, 127 antagonism, 215 structure, 127 5a-Petromyzonol sulfate, 163-164 Rubredoxins, 21 Phaeomelanins, 179-180 Phalloidin, in Amanita, 270 Safrole, 348 Phenethanolamine N-methyltransferase, 77 Salicylamide, 300 Phenothiazine, 271 Salvarsan, 203-204 3' -Phosphoadenosine monophosphate, 19 Sanfilippo syndromes 3'-Phosphoadenosine phosphosulfate, 19 distinction from Morquio syndromes, Phospholipids 396 and sulfur adhesion, 26 metabolic causes, 394-395 and taurine, 161 urinary heparan sulfate, 391 4' -Phosphopantothenic acid, cysteine Sarcolemma, 160 carrier, 138 Sarcoplasmic reticulum, 161 Phototrophism, 12 Sarcosine oxidase, 65 Phyllokinin, 308, 325 Sassafras, 348 Plastocyanins, 207 Scheie syndrome, 397 Platelet sulfotransferase, 314 Selenate, 27 Pliny the Elder, 304 Selenocysteine, in glutathione peroxidase, Porphyra, 341 251 Porphyran, 344 Seminolipid Primaquine, hemolytic anemia, 425 formation, 309 Protein disulfide reductase (E.C.I.6.4.4), structure, 321-322 219 Serotonin 0-sulfonate, 300 Proteoglycans Shiitake Lentinus edod£'.1", 4 calcium binding, 337 Sialic acid, sulfonation, 341 cystathionine {:!-synthase deficiency, 371 Sinigrin, 269 Psychosine sulfate, 309 Siroheme, 23 Putrescine, 79, 81-83 Skatoxyl sulfate, 300 Pyridoxal phosphate Skin color, 179 y-cystathionase deficiency, 371 Sly syndrome, 397 in cystathionine {:!-synthase deficiency, Smooth endoplasmic reticulum, xenobiotic 368 metabolism, 414 sulfur amino acid metabolism, 368 Spermidine Pyruvate dehydrogenase enzymology, 83 inhibition by lewisite, 205 formation, 79 lipoic acid, 254-255 trophic responses, 82 thioester formation, 230 Spermidine synthase (E.C.2.5.1.16), 83 Spermine, 79, 83 Renilla reniform is, 308 Spermine synthase (E.C.2.5.1.22), 83 Retina, taurine levels, 142 Sphingolipids "Reverse" (E.C.l.8.-.-), in myelin, 323 24 structure, 321 Rhizobitoxin, 39 Sphingosines, 321 Rhodanese (E.C.2.8.1.1) Steroid sulfate sulfatase deficiency, 384 detoxification, 127-129 Steroid sulfate (E.C.3.1.6.2) cyanolysis, 220 number, 382 distribution, 125 in placenta, 384 phylogenetic, 128 Storage diseases, 387 444 Index

Succinylthiokinase (E.C.6.2.1.4). 229-230 Tapetum lucidum (cont.) Sulfate taurine deficiency, 155, 158-159 reduction, 19 Taurine transport, 27 biological properties, 150 xenobiotic metabolism. 415 cerebellar ontogeny, 152 Sulfate polysacchrides, 3 depletion. 151 Sulfates in plants, 319 half-life of exchange, 146 Sulfatides, 3 in the human diet, 148 . definition, 293 in milk. 149 Sulfenic acids, 217 in utero. 145-146 Sulfinic acids, oxidation, 210 origin in mice, 143 Sulfinoacetaldehyde, 135 origin in rats, 143-146 Sulfite Taurine aminotransferase (E.C.2.6.1.55). information of , 26 170 reduction, 19-22 Taurine antagonist. 152 deficiency, 374 Tetrathionate Sulfite (E.C.I.8.3.1), 26 accumulation. 24 Sulfite reductase (E.C.I.8.7.-;1.8.99.-) reduction. 20 in APS pathway, 31 Thiamine in dissimilatory reduction. 22 biochemistry, 274-280 Sulfoacetaldehyde. 170 dehydrogenase cofactor. 255 S-Sulfocysteine, 130 reactivity, 3 Sulfonation Thiazolidines, 213-214 bile salts, 318 Thienamycin definition, 293 structure activity, 288 enzymology, 301-308 thioether structure, 271 hydroxamates, 345 Thioacids Sulfotransferases (E.C.2.8.2.-) acidity, 221 biochemistry, 301-308 resonance forms, 221 distribution, 431 Thiocystine, rhodanese. 127 isozymes, 430 Thioesters, a-activation. 232 selectivity. 431 Thioether Sulfur polarizability, 272 formation, 26 terminology. 269 polarizability. 199 Thiokinase (E.C.6.2.1.-). 229 reduction, 20 Thiol disulfide exchange, 217-218 Sulfur dioxide Thiol transferase (E.C.2.5.1.18). 251 from coal, I (E.C.3.1.2.14) oxidation, 130 fatty acid synthesis, 239-240 Sulfur reductase. 21 reversal. 232-233 Sulfuric acid, I Thiolutin, 199 (E.C.2.8.1.-), 124-129 Thiomethyl propionate, in pineapples, 269 Superoxide, 250 (E.C.I.6.4.-), 219 Sym-norspermidine. 84-85 Thioredoxins. 256-257 Sym-norspermine, 84-85 Thiostrepton. 271 Thiosulfate, 20. 24, 26 TAG, 152 Thiosulfate reductase (E.C.2.8.1.3). 22, Tapetum lucidum 128-129 S-adenosylmethylthiopropylamine in, 75 Thiosulfate sulfurtransferase structure, 155 (E.C.2.8.1.1.). 127-129 Index 445

Thiosulfinates, 209-210 Tyrian purple, 304-305 Thiosulfite, 19 Tyrocidins, 244 2-Thiouracil, 199 L~Tyrosine 0-sulfate Thromboembolism, cystathioine hydrolysis by sulfatase A, 309 {:l-synthase deficiency, 370 in urine, 301 Thyrotropin, 78 Transsulfuration, in cystathioine UDP-glucuronosyltransferases, 414 f:l-synthase deficiency. 361 Urothion, 271 Trichochromes, 179-180 Trithionate, 22 Trithionate reductase, 22 Xanthine oxidase, 374 Trypanosomiasis, 204 Xanthommatin, 304 Tumors, proteoglycan levels, 340 Tyramine, 316 Zinc cysteinate, 155