Subject Index acetals 139 adamantyloxycarbonyl group 134, 142, S-acetamidomethyl group 146, 229, 238 149, 154, 205 acetic anhydride 261 additives see auxiliary nuc1eophiles acetimidylation 243 affinity chromatography 309 acetoacetic acid 90 aggregation of peptides 309 acetoacetyl group 94 alanine 169, 197 acetonitrile 182 L-alanyl-L-alanine p-nitrobenzyl ester 177 4-acetoxybenzyloxycarbonyl group 110 alcalase 302 acetylacetone see pentane-2,4-dione alcoholysis 259 acetyl-D-alloisoleucylglycyl ethyl ester alkoxyacetylenes 39, 41 175 alkylation 64, 69, 82, 142, 152, 193, 200, acetylamino acids 172 206,208 acetylation 65, 135, 136 alkyl dithiocarbamoyl group 102 S-acetyl cysteine 141 allyl bromide· 294 acetyl group 134, 182, 302 allyloxycarbonyl group 300 acetyl-imidazole 261 amanitin 239 acetyl-L-isoleucine 175 amino acid nitriles 309 acetyl-L-phenylalanyl-L-alanine methyl D-aminoacid-oxidase 27 ester 176 a-amino-w-azido acids 135 Q-acetyl-serine 136, 138 aminobenzyhydryl resin 258 N-acetyl-DL-threonine 137 S-p-aminobenzyl group 143 acid chlorides 10-12, 21, 29, 273 a-arninobutyric acid 208 acid fluorides 273 2-arnino-6-nitro-caproic acid 74, 134 acid hydrazides 17, 82 6-arninopenicillanic acid 91 acidolysis 2, 77, 79, 88, 107, 137 150, aminopeptidases 191 153, 156, 159, 176, 201, 203, 206, 216, aminosuccinimide derivatives 81, 170, 217,219,221,224,234,251,255,257, 187, 190, 191, 202, 203, 204, 260, 306 260, 293, 302, 306 2-arninothiophenol 93 activated esters, see active esters ammonium formate 306 active esters 3, 31, 34, 35, 51, 54, 55, 147, ammonolysis 30, 79, 85, 161, 187, 200, 148, 171, 188, 196, 226, 239, 253, 267, 205,259 276, 277, 303 ferf-amyloxycarbonyl group 103 acyldiimides 87 Anderson-Callahan model 175 acyldiketopiperazines 186, 198, 199 angiotensins 222, 267 O-acylhydroxylamines 47 anisole 192, 203, 260, 289, 301 acylimidazoles 46, 152, 154 9-anthracenesulfonyl group 297 O-acylisolurea derivatives 40, 45, 51, 54, 9-anthranylmethylesters 79 184, 197, 199, 257, 278, 305 antiparallel beta sheets 233 acyl-lysine deacylase 73, 93, 134 arginine 147, 148, 149, 178,200,205, acyl migration, N to 0 200 218, 265, 284, 296, 307, 309 acyloxyphosphoninum salts 46, 47 aryl carbonates 103 N-acylthiazolidinethions 283 aryl esters 31, 35-37, 44, 47, 86, 277 N-acylurea derivatives 51, 199, 235, 256, aryl isopropenyl carbonates 277 305 aryl phosphites 37 adamantyl esters 306 arylsulfate hydrolase 310 320 Subject Index aryl sulfites 37 benzyl chloroformate see benzyl chlorocar­ aryl sulfonyl groups 206 bonate aryl trifluoroacetates 37 S-benzylcysteine 79, 231, 300, 306 asparagine 10, 84, 130, 159, 203, 204, benzyl esters 75, 77, 79, 80, 185, 186, 219, 256, 306 190, 191, 216, 218, 253, 258, 259, 290 tert. butyl ester 203 benzyl ethers 137, 216, 218 aspartame 285 N-benzyl groups 88, 199, 207, 217 aspartic acid 26, 65, 75, 127, 128, 170, O-benzyl groups 192 194, 195, 202, 294, 306 S-benzyl groups 142 dibenzyl ester 128 S-benzyl-homocysteine 192 aspartyl-glycine sequence 306 benzyloxycarbonyl-L-alanyl-D-alanine 177 aspartyl-proline bond 199 benzyloxycarbonylamino acid urethane aspartyl-proline sequence 202 hydrolase 310 auxiliary nucleopbiles 36, 45, 47, 51, 52, benzylocarbonyl-arninosuccinyl-arnino acids 179, 184, 236, 256, 261 and peptides 187 azide method 3, 10, 16, 17, 19,20,29, N a -benzyloxycarbonyl-L-arginine 147, 54, 79, 88, 104, 127, 135, 179, 180, 183, 302 188, 196, 205, 219, 223, 224, 233, 236, benzyloxycarbonyl-L-asparagine 128 266, 281 benzyloxycarbonyl-L-aspartic acid a-benzyl a-azido acids 74 ester 130 azlactones 41, 51, 171, 173, 181, 182, 195 benzyloxycarbonyl-L-aspartic acid a-methyl azodicarboxylic acid di-tert-butyl ester 129 ester 286 benzyloxycarbonyl-aspartyl-phenylalanine methyl ester 284 Bates' reagent 46, 47 benzyloxycarbonyl-p-benzylaspartyl-amino Beckmann rearrangement 237 acid residues 187 benzaldehyde, Shiff bases with 89 N-benzyloxycarbonyl-S-benzyl-L-cys- benzenesulfonic acid 77 teine 171, 181 imide 114 N-benzyloxycarbonyl-S-benzyl-DL-cysteine benzenesulfonyl group 149 p-nitrophenyl ester 171 benzhydryl see diphenylmethyl S-benzyloxycarbonyl-cysteine 141 benzindenylmethyloxycarbonyl group 290 benzyloxycarbonyl-glycine 194, 198 5-benzisoxazylmethyloxycarbonyl benzyloxycarbonyl- group 110 glycyl-L-alanyl-L-phenylalanyl-glycine benzoin 282 ethyl ester 175 benzophenone hydrazone 78, 298 benzyloxycarbonyl-glycyl-glycine 198 benzosultones 277, 280 benzyloxycarbonyl­ 1-benzotriazolyloxy- glycyl-L-phenylalanine 175 tri(dimethylarnino)phosphonium hex­ benzyloxycarbonyl-glycyl-L-proline p­ afluorophosphate (BOP reagent) 279, nitrophenyl ester 199 286 benzyloxycarbonyl group 2, 11, 18, O-benzotriazolyl-tetramethylisouronium 66-68, 75, 77, 87 -89, 96, 98, 102, hexafluorophosphate (HBTU) 278 103,106-108,131,133-135,142,149, benzoylacetone 90 154, 157, 159, 160, 173, 182, 187, 192, benzoylamino acids 172 193,202,206,208,216,217,243,267, benzoylation 65, 135 300, 310 benzoylglycine 21, 30 Na-benzyloxycarbonyl-histidine 153 benzoyl group 182, 302 N'-benzyloxycarbonyl-hydrazides 87 benzoyl-L-Ieucine 174, 175, 177 benzyloxycarbonyl-L-leucine 177 p-nitrophenyl ester 172, 181 benzyloxycarbonyl- benzoyl-Ieucyl-glycine ethyl ester 172, 177 L-Ieucyl-L-phenylalanine 175 benzyl acetate 192 N"-benzyloxycarbonyl-L-Iysine 194 p-benzyl-aspartyl peptides 128, 191, 306 benzyl ester 176 benzyl bromide 137, 153, 159 methyl ester 176 benzyl chloride 152, 182 Na-benzyloxycar­ benzyl chlorocarbonate 67, 103 bonyl-N"-phenacyl-L-histidine 156 Subject Index 321 benzyloxycarbonyl-L-phenylalanyl-glycine tert-butyldimethylsilyl ethyl ester 187 trifluoromethanesulfonate 300 benzyloxycarbonyl-phenylglycine 181 tert-butyl esters 53, 186, 192, 203 benzyloxycarbonyl-L-tryptophyl-glycine tert-butyl ethers 137 ethyl ester 187, 202 S-tert-butyl group 145 benzyloxycarbonyl-L-valine 183 S-tert-butylmercapto cysteine 140 benzyloxycarbonyl-valyl-tyrosine 183 tert.-butyloxycarbonyl-O-ben- benzyloxymethyl group 298 zyl-L-threonine 137 2-benzyloxyphenyl esters 86 Na-tert-butyloxycarbonyl-N "-benzyloxy- O-benzyl-serine 171 methyl-L-histidine 156 benzylsulfonyl group 113 S-tert-butyloxycarbonyl-cysteine 140 S-benzylthiomethyl group 145 tert-butyloxycarbonyl-glutamine 205 O-benzyl-threonine 137, 306 tert-butyloxycarbonyl-glycine 307 benzyl trichloracetimidate 300 tert-butyloxycarbonyl (Boc) group 2, 3, benzyl trifluoroacetate 157, 159, 192, 306 18, 69, 88, 103, 104, 107, 108, 133, 134, O-benzyl-tyrosine 138 142, 147, 149, 154, 155, 157, 173, 192, 3-benzyl-tyrosine 138, 200, 306 217,218, 243, 250, 251, 254, 267, 274, bicyclic peptides 238 293, 295, 299, 301-303, 308 biphenylylisopropyloxycarbonyl (Bpoc) tert-butyloxycarbonyl-L-methionine p­ group 3, 89, 104, 108, 134, 217, 255, nitrophenyl ester 258, 301 S-methyl p-toluenesulfonate 158 bisbenzyloxycarbonyl-L-cystine N-tert-butyloxycarbonyl-O-me­ dichloride 230 thyl-L-serine 139 N,N' -bis(2-keto-3-oxazolidinyl)phosphinic N-tert-butyloxycarbonyl-O-me- acid (BOP-CI) 280 thyl-L-threonine 139 Boc group see tert-butyloxycarbonyl group tert-butyloxycarbonyl-L-serine 137 BOP reagent see Ben- O-tert-butyloxycarbonyl-tyrosine 136 zotriazolyl-l-oxy( dimethylamino )-phosp­ tert-butyloxycarbonyl-L-valine 173, 183 honium hexafluorophosphate tert-butyloxymethyl group 298, 307 bornyloxycarbonyl group 109 tert-butyl pyrocarbonate 104 boron tribromide 148 tert-butyl trifluoroacetate 69, 107, 159 boron trifluoride ethereate 108, 157, 207, Nintert-butyl-tryptophan 193 243, 300 boron tri-trifluoroacetate 148 cadmium, reduction with 301 Bpoc group see biphenylylisopropyloxycar- calcitonin 6, 238 bonyl group camphorquinone-l0-sulfonic acid 151 bromine water 90, 158 carbanions 70 bromoacetonitrile 14, 30 O-carbamoyl group 136 w-bromoacetophenone 80 carbobenzoxy group see benyzloxycarbonyl 0-2-bromobenzyloxycarbonyl-tyrosine group 136 carbobenzyloxy group see benzyloxycar­ 2-bromoethyl esters 288 bonyl group 4-bromophenylesters 81 carbodiimides 36, 39, 41, 51, 78, 148, bromphenol blue 309 180, 194-197, 200, 204, 226, 235, 253, 3-bromopyridine 256, 267, 274, 286 N-bromosuccinimide 290 water soluble 40, 183, 199, 206, 224, Bunte salts see S-sulfonates 303, 306 tert-butyl acetate, transesterification carbonyldiimidazole (CD!) 46, 104, 152, with 84, 128 189, 253, 275, 279 tert-butyl aminocarbonate 299 carbonyl sulfide 97 p-tert-butyl aspartate 130, 187 carboxamidomethyl esters 289 tert-butyl azidoformate 103 N-carboxyanhydrides (NCA-s) 11, 25, 26, tert-butyl dicarbonate see tert-butyl 28, 92, 182, 226, 240, 268, 275 pyrocarbonate carboxypeptidases 178, 224 tert-butyldimethylsilyloxycarbonyl carboline derivatives 201 group 300 catalysis 309 322 Subject Index catalytic reduction see catalytic hydrogena­ /J-cyclohexyl aspartate 187, 191 tion O-cyclohexyl-tyrosine 200 catalytic hydrogenation 2, 67, 88, 91, 92, cyclo-pentapeptides 238 99, 101, 106, 107, 111, 116, 130, 137, /J-cyclopentyl asparate 191 138, 153, 157, 159, 201, 202, 207, 208, cyclopeptides 232 217 - 220, 234, 235, 259, 266, 289, 295, cyclo-L-cysteine 238 300, 306, 307 cyclodimerization 232 - 234 in liquid ammonia 68, 107, 148 cyclosemigrarnicidine S 234 in the presence of base 133 cysteic acid 95 transfer 68, 107, 148, 157, 294, 306 cysteine 63, 114, 139-141, 195, 207, 216, cesium salts 253 220, 229, 239, 254, 307 chaotropic salts 308 L-cysteinyl-L-cysteine 238 chloroacetyl group 93 cystine 139, 140, 178, 228, 230 chloroacetonitrile 14, 30 2,7-cystine-gramicidin S 239 4-chlorobenzyl esters 285 cytochrome C 242 2-chlorobenzyloxycarbonyl group 134, 255 4-chlorobenzyloxycarbonyl