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xvii | |
Abbreviations |
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xxi | |
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Introduction---a retrospective viewpoint |
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1 | (8) |
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9 | (32) |
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The solid phase principle |
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9 | (2) |
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11 | (1) |
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11 | (30) |
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13 | (2) |
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15 | (11) |
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Side-chain protecting groups |
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26 | (1) |
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26 | (1) |
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27 | (1) |
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N-Fmoc deprotection reaction |
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27 | (3) |
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30 | (1) |
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31 | (1) |
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32 | (4) |
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36 | (1) |
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36 | (1) |
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37 | (4) |
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41 | (36) |
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41 | (1) |
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41 | (1) |
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41 | (3) |
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44 | (1) |
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Attachment of the first residue |
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44 | (7) |
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Hydroxymethyl-based resins |
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44 | (6) |
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50 | (1) |
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Aminomethyl-based linkers |
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51 | (1) |
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51 | (1) |
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52 | (8) |
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53 | (1) |
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54 | (1) |
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55 | (2) |
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Aminium/phosphonium activation methods |
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57 | (2) |
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59 | (1) |
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Assembly of the peptide chain |
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60 | (1) |
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61 | (3) |
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61 | (1) |
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Bromophenol blue monitoring |
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62 | (1) |
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62 | (1) |
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63 | (1) |
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64 | (13) |
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Preparing the resin for cleavage |
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64 | (1) |
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Cleavage reactions releasing fully deprotected peptides |
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65 | (5) |
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70 | (2) |
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Monitoring the cleavage reaction |
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72 | (1) |
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Release of fully protected peptides from hyper-acid labile supports with 1% TFA |
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73 | (1) |
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74 | (3) |
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Preparation and handling of peptides containing methionine and cysteine |
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77 | (38) |
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77 | (1) |
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78 | (3) |
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81 | (34) |
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81 | (6) |
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Solid phase synthesis of cysteine-containing peptides |
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87 | (4) |
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91 | (18) |
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109 | (6) |
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115 | (22) |
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115 | (1) |
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Difficult peptides--an overview |
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115 | (4) |
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115 | (2) |
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Identifying the effects of aggregation |
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117 | (1) |
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Effect of resins, solvents, and additives on aggregation |
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118 | (1) |
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Predicting difficult peptide sequences |
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119 | (3) |
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The N-(2-hydroxy-4-methoxybenzyl) (Hmb) backbone amide protecting group |
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122 | (15) |
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Development and preparation of (Hmb) amino acid derivatives |
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122 | (3) |
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Incorporation of N-(2-hydroxy-4-methoxybenzyl)amino acid residues |
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125 | (2) |
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Site selection for Hmb back bone protection |
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127 | (1) |
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Improved difficult peptide syntheses through Hmb backbone protection |
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128 | (3) |
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Use of Hmb protection to increase solution solubility |
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131 | (1) |
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132 | (5) |
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Synthesis of modified peptides |
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137 | (46) |
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137 | (29) |
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137 | (4) |
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Use of the 4-hydroxymethylbenzoic acid linkage agent for the synthesis of C-terminal modified peptides |
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141 | (8) |
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149 | (4) |
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Peptide aldehydes by solid phase synthesis |
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153 | (8) |
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Synthesis of C-terminal peptide aldehydes on the Multipin™ system using the oxazolidine linker |
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161 | (5) |
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166 | (3) |
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167 | (1) |
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168 | (1) |
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169 | (14) |
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169 | (1) |
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Strategy design in the synthesis of atypical peptides |
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169 | (9) |
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178 | (5) |
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183 | (12) |
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183 | (1) |
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183 | (4) |
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183 | (1) |
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184 | (1) |
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185 | (2) |
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187 | (5) |
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187 | (2) |
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General protocol for post-synthetic phosphorylation |
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189 | (1) |
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190 | (1) |
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Thiophosphorylated peptides |
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191 | (1) |
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Analysis of phosphopetides |
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192 | (3) |
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192 | (1) |
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192 | (1) |
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193 | (2) |
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195 | (20) |
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195 | (2) |
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Strategic considerations in glycopeptide synthesis |
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197 | (1) |
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Formation of glycosidic linkages to amino acids |
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198 | (2) |
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Choosing protective groups for glycosylated amino acids |
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200 | (3) |
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Protection of the α-amino group |
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200 | (1) |
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Protection of the α-carboxyl group |
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201 | (1) |
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Protection of the carbohydrate hydroxyl groups |
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201 | (1) |
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Suitable linkers and resins |
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202 | (1) |
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Preparation of glycosylated amino acids |
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203 | (6) |
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Synthesis of a glycopetide from HIV gp120 |
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209 | (6) |
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211 | (4) |
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Convergent peptide synthesis |
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215 | (14) |
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215 | (1) |
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Strategy in convergent synthesis |
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215 | (1) |
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Solid phase synthesis of protected peptide fragments |
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216 | (4) |
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216 | (1) |
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Synthesis of protected peptide fragments |
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216 | (4) |
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Solid phase fragment condensation |
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220 | (3) |
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Esterification of the C-terminal fragment on 2-chlorotrityl chloride resin |
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220 | (1) |
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Activation and condensation of protected peptide fragments |
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221 | (2) |
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Phase and direction change |
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223 | (4) |
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Fragment condensation in solution |
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223 | (2) |
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Two-directional synthesis. Attachment of fragments on resins of the trityl-type through an amino acid side chain functional group |
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225 | (2) |
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Deprotection, purification, and purity determination of the synthetic peptides |
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227 | (2) |
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227 | (2) |
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Methods of preparing peptide---carrier conjugates |
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229 | (14) |
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229 | (1) |
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Homobifunctional cross-linking |
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229 | (2) |
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Heterobifunctional cross-linking |
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231 | (5) |
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Conjugation of thiol-containing peptides to proteins |
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231 | (3) |
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Conjugation of peptides to thiolated carriers |
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234 | (2) |
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MAP-core constructs as peptide-carriers |
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236 | (7) |
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Sequential synthesis of MAPs |
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237 | (1) |
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Synthesis of MAPs by fragment condensation |
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237 | (2) |
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239 | (4) |
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Chemoselective and orthogonal ligation techniques |
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243 | (22) |
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243 | (1) |
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Chemoselective non-amide ligation |
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244 | (8) |
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245 | (2) |
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247 | (5) |
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Orthogonal amide ligation |
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252 | (13) |
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252 | (6) |
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258 | (4) |
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262 | (3) |
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Purification of large peptides using chemoselective tags |
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265 | (12) |
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265 | (1) |
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Purification of large polypeptides using Fmoc-based chromatographic probes |
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266 | (2) |
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The concept of selective and reversible labelling |
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266 | (2) |
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Capping of unreacted polypeptide chains in SPPS |
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268 | (1) |
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RP-HPLC using lipophilic chromatographic probes |
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269 | (5) |
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Affinity chromatography using biotinylated chromatographic probes |
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274 | (3) |
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276 | (1) |
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Instrumentation for automated solid phase peptide synthesis |
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277 | (26) |
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277 | (2) |
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Batchwise peptide synthesis |
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279 | (8) |
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PE Biosystems Model 433A peptide synthesis system |
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280 | (3) |
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Protein Technologies, Inc., SONATA/Pilot™ peptide synthesizer |
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283 | (1) |
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Protein Technologies Inc., Model PS3™ peptide synthesizer |
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283 | (1) |
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Advanced ChemTech Model 90 peptide synthesizer |
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284 | (2) |
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Advanced ChemTech Model 400 production-scale synthesizer |
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286 | (1) |
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ABIMED EPS 221 synthesizer |
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287 | (1) |
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Continuous-flow peptide synthesis |
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287 | (4) |
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PE Biosystems Pioneer™ peptide synthesis system |
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289 | (2) |
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Multiple peptide synthesis systems |
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291 | (8) |
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PE Biosystems Pioneer MPS option |
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291 | (1) |
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Protein Technologies, Inc., SYMPHONY/Multiplex™ peptide synthesizer |
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292 | (1) |
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Advanced ChemTech Models 348, 396, and 357 bimolecular synthesizers |
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293 | (1) |
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ABIMED AMS 422 multiple peptide synthesizer |
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294 | (2) |
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ABIMED ASP 222 Auto-Spot Robot |
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296 | (1) |
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ZINSSER ANALYTIC SMPS 350 multiple peptide synthesizer |
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297 | (1) |
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ZINSSER ANALYTIC SOPHAS solid phase synthesizer |
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298 | (1) |
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SHIMADZU PSSM-8 peptide synthesizer |
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298 | (1) |
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299 | (4) |
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300 | (3) |
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Manual multiple synthesis methods |
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303 | (26) |
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Simultaneous multiple peptide synthesis---the T-bag method |
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303 | (2) |
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303 | (1) |
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303 | (2) |
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Multiple peptide synthesis with the SPOT-technique |
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305 | (9) |
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305 | (3) |
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Synthesis of peptide SPOT-arrays |
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308 | (5) |
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Applications of peptide SPOT-arrays |
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313 | (1) |
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Manual multipeptide synthesis in block arrays |
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314 | (5) |
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314 | (1) |
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315 | (2) |
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317 | (2) |
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Synthesis of peptides by the Multipin™ method |
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319 | (10) |
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319 | (1) |
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320 | (1) |
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321 | (4) |
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325 | (4) |
Appendices |
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329 | (12) |
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A1 Equipment and reagents for peptide synthesis |
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329 | (2) |
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331 | (6) |
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337 | (4) |
Index |
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341 | |