ABSTRACT

D-Phe-D-Arg-OH 206 9 Acetyl-bradykinin Ac-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH 207 9 [Thr6 [-bradykinin H-Arg-Pro-Pro-Gly-Phe-Thr-Pro-Phe-Arg-OH 208 9 jphe6 [-bradykinin H-Arg-Pro-Pro-Gly-Phe-Phe-Pro-Phe-Arg-OH 209 9 (Lys(Tos)6 [-bradykinin H-Arg-Pro-Pro-Gly-Phe-Lys(Tos)-Pro-Phe-Arg-OH 210 9 [D-Pro2 [-bradykinin H-Arg-D-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH 211 9 [D-Pro3 [-bradykinin H-Arg-Pro-D-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH 212 9 [D-Pro7 j-bradykinin H-Arg-Pro-Pro-Gly-Phe-Ser-D-Pro-Phe-Arg-OH 213 9 Acetyl-[D-Pro7 J-bradykinin Ac-Arg-Pro-Pro-Gly-Phe-Ser-D-Pro-Phe-Arg-OH 214 9 [D-Arg9 J-bradykinin H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-D-Arg-OH 215 9 [T y r(Me) 5 ’8 [-bradykinin FI-Arg-Pro-Pro-Gly-Tyr(Me)-Ser-Pro-Tyr(Me)-

Arg-OH 216 9 Acetyl-[T yr(Me) 5 •8 J-bradykinin Ac-Arg-Pro-Pro-Gly-Tyr(Me)-Ser-Pro-Tyr(Me)-

Arg-OH 217 9 [Thr6,Leu8 J-bradykinin H-Arg-Pro-Pro-Gly-Phe-Thr-Pro-Leu-Arg-OH 218 9 |Gly6,Tyr(Me)8 [-bradykinin H-Arg-Pro-Pro-Gly-Phe-Gly-Pro-Tyr(Me)-Arg-OH 219 9 Acetyl-[Gly6,T yr(Me)8 [-bradykinin Ac-Arg-Pro-Pro-Gly-Phe-Gly-Pro-Tyr(Me)-Arg-OH 220 9 [D-Pro2 3,7 J-bradykinin H-Arg-D-Pro-D-Pro-Gly-Phe-Ser-D-Pro-Phe-Arg-OH 221 9 [Leu5 8,Thr6 J-bradykinin H-Arg-Pro-Pro-Gly-Leu-Thr-Pro-Leu-Arg-OH 222 9 [Leu5 *8,Gly6 j-bradykinin H-Arg-Pro-Pro-Gly-Leu-Gly-Pro-Leu-Arg-OH 223 9 [T yr(Me)5,8,Gly6 |-bradykinin H-Arg-Pro-Pro-Gly-Tyr(Me)-Gly-Pro-Tyr(Me)-

Arg-OH 224 9 [T yr(Me)5,8, Asn6 J-bradykinin H-Arg-Pro-Pro-Gly-Tyr(Me)-Asn-Pro-Tyr(Me)-

Arg-OH 225 9 [D-Arg1,9,D-Phe5,8,D-Ser6|-bradykinin H-D-Arg-Pro-Pro-Gly-D-Phe-D-Ser-Pro-D-Phe-

D-Arg-OH 226 9 Des-Arg1 -endo-Phe8"-bradykinin H-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Phe-Arg-OH

Entry number

Refer­ ence

Solid support Type of bond

Monomer protection

Coupling reagent

Deprotection Cleavage

155 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 156 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 157 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 158 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 159 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 160 S-DVB-2% Bzl Boc DCC TFA HBr-HOAc 161 S-DVB-2% Bzl Boc DCC HCr-HOAc HBr-TFA 162 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

163 S-DVB-2% Bzl Boc OSu,ONp HCl-Diox. HBr-TFA

164 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 165 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 166 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 167 S-DVB-2% Bzl Boc NEPIS HCl-HOAc HBr-TFA 168 S-DVB-2% Bzl Boc DCC,

Mixed anh. HCl-HOAc HBr-TFA

169 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 170 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

171 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 172 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 173 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 174 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA 175 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 176 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 177 S-DVB-2% Bzl Boc NEPIS,

Azide HCl-Diox. HBr-TFA

178 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 179 S-DVB-2% Bzl Boc Mixed anh. TFA-CH2C12 HBr-TFA 200 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

201 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 202 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc-BME HF 203 , S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 204 S-DVB-2% Bzl Boc DCC HCl-HOAc HF 205 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

206 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 207 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 208 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 209 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 210 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 211 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 212 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 213 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 214 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 215 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

216 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

217 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 218 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 219 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 220 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 221 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 222 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 223 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

224 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

225 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

226 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

18 18 18 18 18 19 38 93

71 17 91 71 40

59 45

92 92 92 107 97 97 69

71 103 108

125 60 20 21 14 22

18 18 18 18 18 18 18 18 18 18

18 18 18 18 18 18 18

Entry number

Number of Trivial name or source Sequence residues

227 9 Des-Arg^bradykininyl-glycine H-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-Gly-OH 228 9 Des-Arg'-bradykininyl-arginine H-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-Arg-OH 229 9 Des-Arg1 - |Tyr(Me)5 8 )-bradykininyl-glycine H-Pro-Pro-Gly-Tyr(Me)-Ser-Pro-Tyr(Me)-Arg-

Gly-OH 230 9 D-Retrobradykinin D-Arg-D-Phe-D-Pro-D-Ser-D-Phe-Gly-D-Pro-D-Pro-

D-Arg-OH 231 9 Lysine vasopressin, protected Tos-Cys(Bzl)-Tyr-Phe-Gln-Asn-Cys(Bzl)-Pro-

LvstTosTGlv-NH i 232 9

1-/ V 1 Ujj %J j i ' i * 2 Chymotrypsin (193-201) nonapeptide H-Gly-Asp-Ser-Gly-Gly-Pro-Leu-Val-Cys(Bzl)-OH

233 9 |Tyr(Me)5,Thr6,Tyr(Me)8J-bradykinin H-Arg-Pro-Pro-Gly-Tyr(Me)-Thr-Pro-Tyr(Me)- Arg-OH

234 9 Oxytocin H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 235 9 Oxytocin H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH 2 236 9 Oxytocin H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 237 9 Oxytocin, protected H-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-

n h 2 238 9 Oxytocin, protected Z-Cys(Bzl)-Tyr(Bzl)-Ile-Gln-Asn-Cys(Bzl)-Pro-

Leu-Gly-NH 239 9 Oxytocin, protected Aoc-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 240 9 Deamino-oxytocin MCP-T yr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH 2 241 9 Deamino-oxytocin, protected MCP(Bzl)-Tyr(Bzl)-Ile-Gln-Asp-Cys(Bzl)-Pro-Leu-

Gly-NH2 242 9 |Lys8|-vasopressin H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2 243 9 ILys8|-vasopressin H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2 244 9 JLys8|-vasopressin, protected Tos-Cys(Bzl)-Tyr-Phe-Gln-Asn-Cys(Bzl)-Pro-

Lys(Tos)-Gly-NH2 245 9 (Lys81-vasopressin, protected Z-Cys(Bzl)-Tyr(Bzl)-Phe-Gln-Asn-Cys(Bzl)-Pro-

LvsfZVGlv-NFL 246 9

y f v-i i j (Ser4,Gln8|-oxytocin H-Cys-Tyr-Ile-Ser-Asn-Cys-Pro-Gln-Gly-NH2

247 9 [Ser4,Gln8|-oxytocin, protected Z-Cys(Bzl)-Tyr(Bzl)-Ile-Ser-(Bzl)-Asn-Cys(Bzl)-ProGln-Glv-NFL

Oxytocinoic acid, protected H-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-LeuGly-OH

249 9 TMV protein-<104-112) H-Thr-Ala-Glu-Thr-Leu-Asp-Ala-Thr-Arg-OH 250 9 DNP-nona lysine Dnp-Lys-Lys-Lys-Lys-D-Lys-Lys-Lys-Lys-Lys-OH 251 9 (Phe8l-oxytocin H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Phe-Gly-NH2 252 9 |Pro4,Ile8)-oxytocin H-Cys-Tyr-Ile-Pro-Asn-Pro-Ile-Gly-NH2 253 9 Oxytocinoic acid methyl ester, protected H-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-

GIv-OMp 254 9

VJljf V_71V1C [Pro4,Gin81-oxytocin H-Cys-Tyr-Ile-Pro-Asn-Cys-Pro-Gln-Gly-NH2

255 9 [Pro 4,Leu8J-oxytocin H-Cys-Tyr-Ile-Pro-Asn-Cys-Pro-Leu-Gly-NH2 256 9 Mellitin-(1-9) H-Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-OH 257 9 Oxytocin methylamide, protected Z-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-

Glv-NHCH, 258 9

vj i y m i 1 1 3 Oxytocin hydrazide, protected Z-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-

Glv-NHNH. 259 9

Glv-NHNHOH 260 9

\j iy im il l iv / i i Ribonuclease-(1-8), protected Boc-Lys(Boc)-Glu(OBu)-Thr-Ala-Ala-Ala-Lys(Z)-

Phe-NHNH2

261 10 TMV Protein (103-112) decapeptide H-Thr-Thr-Ala-Glu-Thr-Leu-Asp-Ala-Thr-Arg-OH 262 10 Nylon 11 oligomers H-[Und]n-OH, n = 2-10 263 10 Nylon 6.6 oligomers H-[NH(CH2)6NHCO(CH2)4CO]n-OH, n = 2-10 264 10 Bradykininyl-glycine H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-Gly-OH 265 10 Endo-Phe8a-bradykinin H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Phe-Arg-OH 266 10 Bradykininyl-arginine H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-Arg-OH 267 10 |Ty r(Me)58 |-bradykininy 1-phenylalanine H-Arg-Pro-Pro-Gly-Tyr(Me)-Ser-Pro-Tyr(Me)-

Arff-Phe-OH 268 10

1 1 1 C"V/ 1 1 [Tyr(Me)5,8l-bradykininyl-glycine H-Arg-Pro-Pro-Gly-Tyr(Me)-Ser-Pro-Tyr(Me)-

Ara-Glv-OH 269 10

r\ i g’Vjiy-wn Gly-|Gly 6,Tyr(Me)8 ]-brady kinin H-Gly-Arg-Pro-Pro-Gly-Phe-Gly-Pro-Tyr(Me)-

Aro Ol-I 270 10

rg-un TMV protein-(103-112) H-Thr-Thr-Ala-Glu-Thr-Leu-Asp-Ala-Thr-Arg-OH

271 10 Staphylococcal nuclease-(108-117), Boc-Leu-Ala-Lys(TFA)-Val-Ala-Tyr-Val-Tyrprotected Lys(TFA)-Pro-OH

Entry number

Refer­ ence

Solid support Type of bond

Monomer protection

Coupling reagent

Deprotection Cleavage

227 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 228 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 229 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

230 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

231 S-DVB-2% Bzl Boc DCC HCl-HOAc N H 3

232 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 233 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

234 , S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH 3-MeOH 235 S-DVB-2% Bzl Nps DCC,ONp HCl-Diox. NH3-MeOH-DMF 236 Phenol-trioxane Phenyl Aoc DCC HCl-MeOH NH3-MeOH 237 S-DVB-2% Bzl Boc ONp,OSu-

triazole HCl-HOAc NH3-MeOH

238 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH 3-MeOH

239 Phenol-trioxane Phenyl Aoc DCC HCl-MeOH NH3-MeOH 240 N 0 2-S-DVB-2 % N 0 2Bzl Boc DCC.ONp HCl-HOAc,TFA NH3-MeOH 241 N 0 2-S-DVB-2% N 0 2Bz1 Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH

242 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 243 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc NH3-EtOH-DMF 244 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc N H 3-EtOH-DMF

245 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc-TFA NH 3-MeOH

246 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 247 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH

248 S-DVB-2% Bzl Boc ONp,OSutriazole

HCl-HOAc NH3-MeOH

249 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 250 S-DVB-2% Bzl Boc,Nps DCC HCl-HOAc HBr-TFA 251 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 252 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 253 S-DVB-2% Bzl Boc ONp,OSu-

triazole HCl-HOAc,HC1 MeOH-A-Methyl

piperidine 254 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 255 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc,TFA NH3-MeOH 256 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 257 S-DVB-2% Bzl Boc ONp,OSu-

triazole HCl-HOAc CH3NH2-MeOH

258 S-DVB-2% Bzl Boc ONp,OSutriazole

HCl-HOAc NH2NH2-MeOH

259 S-DVB-2% Bzl Boc ONp,OSutriazole

HCl-HOAc NH2NHOH-MeOH

260 S-DVB-2% Bzl Boc,Nps DCC,ONp, OPcp

HCl-HOAc,HClDiox. HClHOAc

NH2NH2-DMF

261 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 262 S-DVB-2% Bzl Boc DCC TFA HBr-HOAc 263 S-DVB-2% Bzl Boc DCC TFA HBr-HOAc 264 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 265 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 266 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 267 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

268 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

269 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

270 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 271 S-DVB-2% Bzl Boc OSu,ONp HCl-Diox. HBr-TFA

18 18 18

24 88

42 50 51 70 76

70 44 44

42 23 23

77 77

38 55 112 116 72

122 116 106 58

25 19 19 18 18 18 18

38 13

Entry number

Number of residues

Trivial name or source Sequence

272 10 |GIy5,Gly10]-gramicidin S cyclo[-Val-Orn-Leu-D-Phe-Gly-Val-Orn-Leu-DPhe-Gly-]

273 10 |Glys,Gly10]-gramacidin S cyclo[-Val-Orn-Leu-D-Phe-Gly-Val-Orn-Leu-DPhe-Gly-]

274 10 [He5]-angiotensin I H-Asp-Arg-V al-T y r-1 le-H is-Pro-Phe-H is-Leu-O H 275 10 Alanylalanylalanylalanylalanylleucylas-

partylalanythreonylarginine H-Ala-Ala-Ala-Ala-Ala-Leu-Asp-Ala-Thr-Arg-OH

276 10 Oligolysine H-(Lys)n-OH, n = 2-10 277 10 Antamanide cyclo[-Pro-Phe-Phe-Val-Pro-Pro-Ala-Phe-Phe-

Pro-] 278 11 D-Alanyl-L-alanyl-D-alanyl-L-alanyl-D-

alany 1-L-alany 1-d-alany 1-L-alany 1-DalanyI-L-alanyl-2,4 dinitropheny-L-lysine

H-D-Ala-Ala-D-Ala-Ala-D-Ala-Ala-D-Ala-AlaD-Ala-Ala-Lys(Dnp)-OH

279 11 Met-Lys-bradykinin H-Met-Lys-Arg-Pro-Pro-Gly-Phe-Ser-Pro-PheArg-OH

280 11 Casein peptide H-Val-Asp-Glu-Glu-Glu-DL-Ser-lle-Ala-MetGlu-Lys-OH

281 11 Valylserylglutamylglutamylglutamylaspartyl-H-Val-Ser-Glu-Glu-Glu-Asp-Ile-Ala-Met-Glyisoleucylalanylmethionylglutamyllysine Lys-OH

282 12 Dansyl-oligoprolyl-hydrazide Dansyl-(Pro)n-NHNH2, n = 1-12 283 12 Valinomycin cyclo-[L-Val-D-Hyv-D-Val-L-Lac] 3 284 12 Oligo(glycylprolylprolyl)glycylprolyl-

proline, labelled H-[Gly-Pro-(3,4-3H)-Pro]3-Gly-Pro-Pro-OH

285 12 01igo(glycylprolyl-3-methylprolyl)- glycylproly 1-3-methyl proline

H-[Gly-Pro-Pro(Me)]n-OH n = 1, 2, 3 and 4

286 12 OHgo(glycylprolyl-4-fluoroprolyl)- glycylprolyl-4-fluoroproline

H-[Gly-Pro-Pro(F)]n-OH n = 1, 2, 3 and 4

287 13 Nylon 6 oligomers H-[Cap]n-OH n = 2, 3, 4, 5, 7, 9, 11 and 13 288 14 Glucagon (16-29) H-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Val-Gln-Try-

Leu-Met-Asn-Thr-OH 289 15 Cysteinylalanylvalylcysteinyl-(im-

benzyl)histidylalanylvalylalanyllysylalanylalanyl-alanylalanylalanylalanine

H-Cys-Ala-Val-Cys-His(Bzl)-Ala-Val-Ala-Lys-AlaAla-Ala-Ala-Ala-Ala-OH

290 15 Lysylalanylvalylcysteinylhistidylalanylvalylalanyllysylalanylalanylalanylalanylalanylalanine

H-Lys-Ala-Val-Cys-His-Ala-Val-Ala-Lys-Ala-AlaAla-Ala-Ala-Ala-OH

291 15 Ribonuclease-(1-15) H-Lys-Glu-Thr-Ala-Ala-Ala-Lys-Glu-Phe-Arg-GlnHis-Met-Asp-Ser-OH

292 16 T yrosylhistidy lhistidylphenylalany 1phenylalanylaspartylhistidylserylaspartylserylhistidylphenylalanylaspartylphenylalanylhistidylphenylalanine

H-Tyr-His-His-Phe-Phe-Asp-His-Ser-Asp-Ser-HisPhe-Asp-Phe-His-Phe-OH

293 16 [Ala16 [-ribonuclease-(1-16) H-Lys-Glu-Thr-Ala-Ala-Ala-Lys-Glu-Phe-Arg-GlnHis-Met-Asp-Ser-Ala-OH

294 17 Angiotensinyl-bradykinin H-Asp-Arg-Val-Tyr-lle-His-Pro-Phe-Arg-Pro-ProGly-Phe-Ser-Pro-Phe-Arg-OH

295 18 Bradykininyl-bradykinin H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-ArgPro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH

296 18 Polistes kinin PCA-Tyr-Asn-Lys-Lys-Lys-Leu-Arg-Gly-Arg-ProPro-Gly-Phe-Ser-Pro-Phe-Arg-OH

297 18 Valylserylisoleucylglutamylglutamylglutamylserylserylprolylserylvalylglutamylglutaniylglutamylaspartylserylisoleucylalanine

H-Val-Ser-Ile-Glu-Glu-Glu-Ser-Ser-Pro-Ser-Val-GluGlu-Glu-Asp-Ser-Ile-Ala-OH

298 20 Des lie2-insulin A-chain 5-sulfonate (bovine)

H-Gly-Val-Gly-Gln-Cys(S03)-Cys(S03)-Ala-SerVal-Cys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-TyrCys(S03)-Asn-OH

299 20 Lysylaspartylglutamylglutamylglutamylglutamylvalylglutamylserylphenylalanylserylglycylprolylaspartylalanylprolylleucylprolylalanylglycine

H-Lys-Asp-Glu-Glu-Glu-Glu-Val-Glu-Ser-Phe-SerGly-Pro-Asp-Ala-Pro-Leu-Pro-Ala-Gly-OH

300 21 Insulin A-chain 5-sulfonate (bovine) H-Gly-Ile-Val-Glu-Gln-Cys(S03)-Cys(S03)-Ala-SerVal-Cys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-TyrCys(S03)-Asn-OH

Entry number

Refer­ ence

Solid support Type of bond

Monomer protection

Coupling reagent

Deprotection Cleavage

272 Styrene Bzl Boc OSu HCl-Diox. HBr-HOAc

273 , S-DVB-2 % Bzl Boc DCCOSu HCl-HOAc HBr-TFA

274 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 275 S-DVB-2 % Bzl Boc DCC HCl-HOAc HBr-TFA

276 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA 277 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

278 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

279 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

280 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

281 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

282 S-DVB-2% Bzl Boc DCC HCl-HOAc NH2NH2-EtOH 283 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA 284 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

285 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

286 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

287 S-DVB-2% Bzl Boc Mixed anh. HCl-HOAc HBr-TFA 288 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc-BME HF

289 S-DVB-2% Bzl Boc DCC HCl-HOAc HF

290 S-DVB-2% Bzl Boc DCC HCl-HOAc HF

291 S-DVB-2% Bzl Boc DCC,ONp HCl-Diox. HF,HBr-TFA

292 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

293 S-DVB-2% Bzl Boc DCC,ONp HCl-Diox. HF,HBr-TFA

294 , S-DVB-1 % Bzl Boc DCC HCl-Diox. HBr-TFA

295 S-DVB-2% Bzl NPS DCC HC1 HBr-TFA

296 S-DVB-2% Bzl Boc DCCONp HCl-Diox. HBr-TFA

297 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

298 S-DVB-2% Bzl Boc ONp HCl-HOAc HBr-TFA

299 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

300 S-DVB-2% Bzl Boc DCC HCl-Diox. HBr-TFA

54 80

47 110

75 130

87 74 79

19 60

30 31

Entry Number of Trivial name or source number residues

Sequence

301 21 Insulin A-chain 5-sulfonate (bovine) H-Gly-Ile-Val-Glu-Gln-Cys(S03)-Cys(S03)-AlaSer-Val-Cys(S03)-Ser-Leu-Tyr-G!n-Leu-Glu-AsnTyr-Cys(S03)-Asn-OH

302 21 Insulin A-chain 5-sulfonate (sheep) H-Glu-Ile-Val-Glu-Gln-Cys(S03)-Cys(S03)-AlaGly-Val-Cys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-AsnTyr-Cys(S03)-Asn-OH

H-Gly-Ile-Val-Glu-Gln-Cys(S03)-Cys(S03)-AlaGly-Val-Cys(S03)-Ala-Leu-Ala-Gln-Leu-Glu-AsnTyr-Cys(S03)-Asn-OH

304 21 [Ala^-insulin A-chain 5-sulfonate (bovine) H-Ala-Ile-Val-Glu-Gln-Cys(S03)-Cys(S03)-AlaSer-Val-Cys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-AsnTyr-Cys(S03)-Asn-OH

305 21 [Ala7,Ala20]-insulin A-chain (bovine) H-Gly-Ile-Val-Glu-Gln-Cys-Ala-Ala-Ser-Val-CysSer-Leu-Tyr-Gln-Leu-Glu-Asn-Tyr-Ala-Asn-OH

306 21 Insulin A-chain 5-sulfonate (human) H-Gly-Ile-Val-Glu-Gln-Cys-Cys-Thr-Ser-IleCys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-TyrCys(S03)-Asn-OH

307 21 [Val2 [-insulin A-chain 5-sulfonate (sheep) H-Gly-Val-Val-Glu-Gln-Cys(S03)-Cys(S03)-Ala-GlyVal-Cys(S03)-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-TyrCys(S03)-Asn-OH

H-Gly-Ile-Val-Glu-Glu-Cys(S03)-Cys(S03)-AlaGly-Val-Cys(S03)-Ala-Leu-Ala-Glu-Leu-Glu-AlaPhe-Cys(S03)-Ala-OH

H-Gly-Val-Val-Glu-Glu-Cys(S03)-Cys(S03)-AlaGly-Val-Cys(S03)-Ala-Leu-Ala-Glu-Leu-Glu-AlaPhe-Cys(S03)-Ala-OH

310 21 [Leu2 [-insulin A-chain 5-sulfonate (sheep) H-Gly-Leu-Val-Glu-Gln-Cys(S03)-Ala-Gly-ValCys(S03)-Ser-Leu-Tyr-Gln-Leu-Gln-Asn-TyrCys(S03)-Asn-OH

H-Gly-Ile-Val-Glu-Gln-Ala-Cys(S03)-Ala-GlyVal-Ala-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-TyrCys(S03)-Asn-OH

312 23 Hemoglobin B-chain (124-146) (human) H-Pro-Pro-Val-Gln-Ala-Ala-Tyr-Gln-Lys-Val-ValAla-Gly-Val-Ala-Asn-Ala-Leu-Ala-His-Lys-TyrHis-OH

313 25 Oligoaminocaproic acid amide H[NH(CH2)5CO]n-OH n = 3,5,7,9,11,13,15,17,21,25 314 27 Oligolysyl-decaalanyl-oligolysylglycine H-[Lys]n-[Ala]10-[Lys]n-Gly-OH n = 7.9 315 28 [des-Phe1 ,des-Val2,Ala 4[-insulin B-chain

5-sulfonate (bovine) H-Asn-Ala-His-Leu-Cys(S03)-Gly-Ser-His-LeuVal-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)-GlyGlu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-Lys-Ala-OH

H-Val-Asn-Gln-His-Leu-Cys(S03)-Gly-Ser-HisLeu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-LysAla-OH

317 30 Insulin B-chain 5-sulfonate (bovine) H-Phe-Val-Asn-Gln-His-Leu-Cys(S03)-Gly-SerHis-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-LysAla-OH

318 30 Insulin B-chain 5-sulfonate (human) H-Phe-Va!-Asn-Gln-His-Leu-Cys(S03)-Gly-SerHis-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-LysAla-OH

319 30 |Ala3 [-insulin B-chain 5-sulfonate (bovine) H-Phe-Val-Ala-Gln-His-Leu-Cys(S03)-Gly-SerHis-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-LysAla-OH

320 30 [Ala4|-insulin B-chain 5-sulfonate (bovine) H-Phe-Val-Asn-Ala-His-Leu-Cys(S03)-Gly-SerHis-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-Lys-AlaOH

321 30 [Ala9 [-insulin B-chain 5-sulfonate (bovine) H-Phe-Val-Asn-Gln-His-Leu-Cys(S03)-Gly-AlaHis-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys(S03)- Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-LysAla-OH

Entry number

Refer­ ence

Solid support Type of bond

Monomer protection

Coupling reagent

Deprotection Cleavage

301 S-DVB-2% Bzl Boc ONp HCl-Diox. HBr-TFA

302 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

303 S-DVB-2% Bzl Boc ONp HCl-HOAc HBr-TFA

304 S-DVB-2% Bzl Boc ONp HCl-HOAc HBr-TFA

305 S-DVB-2% Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

306 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

307 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

308 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

309 S-DVB-2% Bzl Boc DCC HCl-HOAc HBr-TFA

310 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

311 S-DVB-2% Bzl Boc ONp HCl-HOAc HBr-TFA

312 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

313 , S-DVB-2% Bzl Boc Mixed anh. HCl-HOAc HBr-TFA 314 S-DVB-2% Bzl Boc NCA,DCC HCl-HOAc HBr-TFA 315 S-DVB-1 % Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

316 S-DVB-1 % Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

317 S-DVB-2% Bzl Boc DCC,Np HCl-HOAc HBr-TFA

318 S-DVB-2% Bzl Boc DCC,ONp HCl-HOAc HBr-TFA

319 S-DVB-1 % Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

320 S-DVB-1 % Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

321 S-DVB-1 % Bzl Boc DCC,ONp HCl-Diox. HBr-TFA

28 102 131 81

33, 34

35, 84

Entry number

Number of residues

Trivial name or source Sequence

322 42 Staphylococcal nuclease (6-47) H-Lys-Leu-His-Lys-Glu-Pro-Ala-Thr-Leu-lleLys-Ala-Ile-Asp-Gly-Asp-Thr-Val-Lys-LeuMet-Tyr-Lys-Gly-Gln-Pro-Met-Thr-Phe-Arg-LeuLeu-Leu-Val-Asp-Thr-Pro-Glu-Thr-Lys-HisPro-OH

323 50 Oligolysyl-oligovalyl-oligolysylglycine (DL-Lys) 1 8-( Val) 15-(DL-Lys) 16-Gly-OH 324 55 Apoferrodoxin 5-sulfonate

C. pasteurianum H-Ala-Tyr-Lys-Ile-Ala-Asp-Ser-Cys(S03)-ValSer-Cys(S03)-Gly-Ala-Cys(S03)-Ala-Ser-GluCys(S03)-Pro-Val-Asn-Ala-Ile-Ser-Gln-Gly-AspSer-lle-Phe-Val-Ile-Asp-Ala-Asp-ThrCys(S03)-!le-Asp-Cys(S03)-Gly-Asn-Cys(S03)-AlaAsn-Val-Cys(S03)-Pro-Val-Gly-Ala-Pro-ValGln-Glu-OH

325 55 Polylysyloligoalanylglycine H(DL-Lys)3 o-(Ala-d4)24-G ly-d2-OH 326 60 Poly(prolylprolylglycyl)prolylprolylglycine H-(Pro-Pro-Gly)20OH 327 104 [His(Bzl)26’33, Phe59]-apocytochrome c

horse heart Ac-Gly-Asp-Val-Glu-Lys-Gly-Lys-Lys-Ile-

Phe-Val-Gln-Lys-Cys-Ala-Glu-Cys-His-ThrVal-Glu-Lys-Gly-Gly-Lys-His-Lys-Thr-GlyPro-Asn-Leu-His-Gly-Leu-Phe-Gly-Arg-LysThr-Gly-Gln-Ala-Pro-Gly-Phe-Thr-Tyr-Thr-AspAla-Asn-Lys-Asn-Lys-Gly-Ile-Thr-Trp-Lys-Glu-GluThr-Leu-Met-Glu-Tyr-Leu-Glu-Asn-Pro-Lys-LysTyr-lle-Pro-Gly-Thr-Lys-Met-lle-Phe-AlaGly-Ile-Lys-Lys-Lys-Thr-Glu-Arg-Glu-AspLeu-Ile-Ala-Tyr-Leu-Lys-Lys-Ala-ThrAsn-Glu-OH

328 124 Pancreatic Ribonuclease A 5-sulfonate (bovine)

H-Lys-Glu-Thr-Ala-Ala-Ala-Lys-Phe-Glu-ArgGln-His-Met-Asp-Ser-Ser-Thr-Ser-Ala-Ala-SerSer-Ser-Asn-Tyr-Cys(S03)-Asn-Gln-MetMet-Lys-Ser-Arg-Asn-Leu-Thr-Lys-Asp-ArgCys(S03)-Lys-Pro-Val-Asn-Thr-Phe-Val-HisGlu-Ser-Leu-Ala-Asp-Val-Gln-Ala-Val-Cys(S03)- Ser-Gln-Lys-Asn-Val-Ala-Cys(S03)-Lys-AsnGly-Gln-Thr-Asn-Cys(S03)-Tyr-Gln-Ser-TyrSer-Thr-Met-Ser-!le-Thr-Asp-Cys(S03)-ArgGlu-Thr-Gly-Ser-Ser-Lys-Tyr-Pro-Asn-Cys(S03)- Ala-Tyr-Lys-Thr-Thr-Gln-Ala-Asn-Lys-His-IleIle-Val-Ala-Cys(S03)-Glu-Gly-Asn-Pro-TyrVal-Pro-Val-His-Phe-Asp-Ala-Ser-Val-OH

Entry number

Refer­ ence

Solid support Type of Monomer Coupling Deprotection Cleavage bond protection reagent

322 S-DVB-2% Bzl Boc DCC,ONp HCl-Diox. HF

323 S-DVB-2% Bzl Boc NCA,DCC HCl-HOAc HBr-TFA 324 S-DVB-2% Bzl Boc DCC.ONp HCl-HOAc HBr-TFA

325 S-DVB-2% Bzl Boc OSu HCl-HOAc HBr-TFA 326 S-DVB-2% Bzl Aoc DCC HCl-HOAc HF 327 S-DVB-2% Bzl Boc DCC,ONp, HCl-Diox. HF

OSu

328 S-DVB-1 % Bzl Boc DCC,ONp TFA-CH2C12 HF

Compiled by G. R. Marshall and R. B. Merrifield.