Introduction to Enzyme and Coenzyme Chemistry - E-Library Home

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Enzymatic Carbon–Carbon Bond Formation 191 C.H. Wong & G.M. Whitesides (1994) Enzymes in Synthetic Organic Chemistry. Pergamon, Oxford. Claisen enzymes S.I. Chang & G.G. Hammes (1990) Structure and mechanism of action of a multifunctional enzyme: fatty acid synthase. Acc. Chem. Res., 23, 363–9. J.D. Clark, S.J. O’Keefe & J.R. Knowles (1988) Malate synthase: proof of a stepwise Claisen condensation using the double-isotope fractionation test. Biochemistry, 27, 5961–71. J.S. Staunton (1991) The extraordinary enzymes involved in erythromycin biosynthesis. Angew. Chem. Intl. Ed. Engl., 30, 1302–6. Carboxylases P.V. Attwood & J.C. Wallace (2002) Chemical and catalytic mechanisms of carboxyl transfer reactions in biotin-dependent enzymes. Acc. Chem. Res., 35, 113–20. P. Dowd, R. Hershline, S.W. Ham & S. Naganathan (1994) Mechanism of action of vitamin K. Nat. Prod. Reports, 11, 251–64. F.C. Hartman & M.R. Harpel (1994) Chemical and genetic probes of the active site of d- ribulose-1,5-bisphosphate carboxylase-oxygenase: a retrospective based on the threedimensional structure. Adv. Enzymol., 66, 1–76. J.R. Knowles (1989) The mechanism of biotin-dependent enzymes. Annu. Rev. Biochem., 58, 195–222. N.F.B. Phillips, M.A. Shoswell, A. Chapman-Smith, D.B. Keech & J.C. Wallace (1992) Isolation of a carboxyphosphate intermediate and the locus of acetyl CoA action in the pyruvate carboxylase reaction. Biochemistry, 31, 9445–50. J.W. Suttie (1985) Vitamin K-dependent carboxylase. Annu. Rev. Biochem., 54, 459–78. Thiamine pyrophosphate F. Jordan (2003) Current mechanistic understanding of thiamin diphosphate-dependent enzymatic reactions. Nat. Prod. Reports, 20, 184–201. R. Kluger, J. Chin, & T. Smyth (1981) Thiamin-catalyzed decarboxylation of pyruvate. Synthesis and reactivity analysis of the central, elusive intermediate, a-lactylthiamin. J. Am. Chem. Soc., 103, 884–8. Terpene cyclases D.E. Cane (1990) Enzymatic formation of sesquiterpenes. Chem. Rev., 90, 1089–103. R.B. Croteau, C.J. Wheeler, D.E. Cane, R. Ebert & H.J. Ha (1987) Isotopically sensitive branching in the formation of cyclic monoterpenes: proof that ( )a-pinene and ( )b-pinene are synthesised by the same monoterpene cyclase via deprotonation of a common intermediate. Biochemistry, 26, 5383–9. C.A. Lesburg, G. Zhai, D.E. Cane, and D.W. Christianson (1997) Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science, 277, 1820–24. M. Seemann, G. Zhai, J.W. de Kraker, C.M. Paschall, D.W. Christianson & D.E. Cane (2002) Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis. J. Am. Chem. Soc., 124, 7681–9.
192 Chapter 7 Radical couplings W.M. Chou & T.M. Kutchan (1998) Enzymatic oxidations in the biosynthesis of complex alkaloids. Plant. J., 15, 289–300. K. Freudenberg (1965) Lignin: its constitution and formation from p-hydroxycinnamyl alcohols. Science, 148, 595–600. T. Higuchi (1971) Formation and biological degradation of lignins. Adv. Enzymol., 34, 207–83. H. Nordlöv & S. Gatenbeck (1982) Enzymatic synthesis of (þ) and ( )- bisdechlorogeodin with sulochrin oxidase from Penicillium frequentans and Oospora sulphurea-ochracea. Arch. Microbiol. 131, 208–11.
Page 1 and 2:
Introduction to Enzyme and Coenzyme
Page 4 and 5:
Introduction to Enzyme and Coenzyme
Page 6 and 7:
Contents Preface Representation of
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Contents vii 8 Enzymatic Addition/E
Page 11 and 12:
Representation of Protein Three-Dim
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2 Chapter 1 H 2 N O NH 2 + H 2 O Ja
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4 Chapter 1 Table 1.1 The vitamins.
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6 Chapter 1 has very diVerent biolo
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2 All Enzymes are Proteins 2.1 Intr
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10 Chapter 2 (Gln). There are three
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12 Chapter 2 AAA Lys ACA Thr AGA Ar
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14 Chapter 2 H N O H N O Figure 2.8
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16 Chapter 2 (a) (b) Figure 2.12 St
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18 Chapter 2 Figure 2.14 Structure
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20 Chapter 2 (a) X Y Enzyme + Subst
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22 Chapter 2 maintaining protein te
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24 Chapter 2 surface glycoprotein g
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26 Chapter 2 O-linked glycosylation
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28 Chapter 2 Metalloproteins I. Ber
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30 Chapter 3 O N H R CO 2 H acylase
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32 Chapter 3 (a) Free energy uncata
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34 Chapter 3 Ester k rel Effective
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36 Chapter 3 3.4 The importance of
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38 Chapter 3 pKa Tyrosine CH 2 O H
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40 Chapter 3 glycoside hydrolysis (
Page 53 and 54:
42 Chapter 3 O O Glu 143 O − R H
Page 55 and 56:
44 Chapter 3 the hydroxyl groups of
Page 57 and 58:
46 Chapter 3 E + S E + S ES' ES ‘
Page 59 and 60:
48 Chapter 3 Examination of protein
Page 61 and 62:
50 Chapter 3 (Note: Similar results
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52 Chapter 4 (1) Direct UV (2) Radi
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54 Chapter 4 Figure 4.3 PuriWcation
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56 Chapter 4 The two kinetic consta
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58 Chapter 4 Lineweaver−Burk Plot
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60 Chapter 4 E + S K i EI+ I ES E +
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62 Chapter 4 (2) by treatment with
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64 Chapter 4 In general the stereoc
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H D T CO 2 H CO − 2 T HO D H −
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68 Chapter 4 4.5 The existence of i
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70 Chapter 4 18O 18O 18 O O P O −
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72 Chapter 4 If a reaction involves
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74 Chapter 4 O D H ketosteroid isom
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76 Chapter 4 Table 4.3 Group speciW
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78 Chapter 4 [S] (mM) Rate of produ
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80 Chapter 4 Enzyme kinetics I.H. S
Page 93 and 94:
82 Chapter 5 O = C NHR peptidase H
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84 Chapter 5 non-speciWc protease c
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86 Chapter 5 His 57 His 57 Asp 102
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88 Chapter 5 Other serine proteases
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90 Chapter 5 Figure 5.8 Structure o
Page 103 and 104:
92 Chapter 5 now predominate Perhap
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OH R O Zn 2+ O O O Ph Glu 270 H 2 N
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96 Chapter 5 CASE STUDY: HIV-1 prot
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98 Chapter 5 HO Transition state pe
Page 111 and 112:
100 Chapter 5 The aminoacyl group o
Page 113 and 114:
102 Chapter 5 5.5 Enzymatic phospho
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Page 117 and 118:
Page 119 and 120:
108 Chapter 5 Adenosine 5 0 -tripho
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110 Chapter 5 functional group. Gly
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112 Chapter 5 CH 2 OH O RO HO OH O
Page 125 and 126:
114 Chapter 5 to these atoms that t
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116 Chapter 5 Problems (1) Using pa
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118 Chapter 5 (6) Retaining glycosi
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120 Chapter 5 J.R. Knowles (1980) E
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122 Chapter 6 +1.0 Redox potential
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Table 6.1 Classes of redox enzymes.
Page 137 and 138:
126 Chapter 6 An important point is
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128 Chapter 6 O H − OH − O OH H
Page 141 and 142:
130 Chapter 6 one-electron transfer
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132 Chapter 6 (a) R N H + N O R N H
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134 Chapter 6 Inactivation by trany
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Page 149 and 150:
138 Chapter 6 (a) (b) Figure 6.23 S
Page 151 and 152: 140 Chapter 6 glutathione called tr
Page 153 and 154: 142 Chapter 6 neither has a stable
Page 155 and 156: 144 Chapter 6 of the haem cofactor
Page 157 and 158: 146 Chapter 6 Figure 6.33 Active si
Page 159 and 160: 148 Chapter 6 HO H N N O O H N prol
Page 161 and 162: 150 Chapter 6 R R R O 2 , Fe 2+ O O
Page 163 and 164: 152 Chapter 6 CoA. Explain these re
Page 165 and 166: 154 Chapter 6 NADH models O. Almars
Page 167 and 168: 7 Enzymatic Carbon-Carbon Bond Form
Page 169 and 170: 158 Chapter 7 O H − OH O − O H
Page 171 and 172: 160 Chapter 7 Figure 7.4 Structure
Page 173 and 174: 162 Chapter 7 Figure 7.6 Active sit
Page 175 and 176: 164 Chapter 7 7.3 Claisen enzymes I
Page 177 and 178: 166 Chapter 7 CoAS O EnzB − H D T
Page 179 and 180: 168 Chapter 7 onto the acetyl-thioe
Page 181 and 182: 170 Chapter 7 In the case of erythr
Page 183 and 184: 172 Chapter 7 O HO O − O ATP ADP
Page 185 and 186: 174 Chapter 7 CO 2 − vitamin K-de
Page 187 and 188: 176 Chapter 7 7.8 Thiamine pyrophos
Page 189 and 190: 178 Chapter 7 HN N + N H NH S O OPP
Page 191 and 192: 180 Chapter 7 O OH OH camphor geran
Page 193 and 194: 182 Chapter 7 CH 3 * OPP (−)pinen
Page 195 and 196: 184 Chapter 7 Figure 7.36 Structure
Page 197 and 198: 186 Chapter 7 C C C C C O OCH 3 C H
Page 199 and 200: 188 Chapter 7 AcO HO HO NHAc O OH +
Page 201: 190 Chapter 7 (9) Usnic acid is a n
Page 205 and 206: 194 Chapter 8 C-O cleavage H E1 H C
Page 207 and 208: 196 Chapter 8 leads to the formatio
Page 209 and 210: 198 Chapter 8 aconitase citrate cis
Page 211 and 212: 200 Chapter 8 *H R H H CO 2 − NH
Page 213 and 214: 202 Chapter 8 EnzB − 2 H − O 2
Page 215 and 216: 204 Chapter 8 involves no change in
Page 217 and 218: 206 Chapter 8 Glyphosate H H N CO
Page 219 and 220: 208 Chapter 8 (5) Chorismic acid (s
Page 221 and 222: 9 Enzymatic Transformations of Amin
Page 223 and 224: CO − − 2 CO 2 H H CO 2 − N +
Page 225 and 226: 214 Chapter 9 - BEnz CO − 2 Cl H
Page 227 and 228: 216 Chapter 9 Arg 292 Arg 292 Lys 2
Page 229 and 230: 218 Chapter 9 Arg 292 Asp 292 HN H
Page 231 and 232: 220 Chapter 9 S − B 1 Enz H − C
Page 233 and 234: 222 Chapter 9 9.6 N-Pyruvoyl-depend
Page 235 and 236: 224 Chapter 9 The biosyntheses of n
Page 237 and 238: 226 Chapter 9 Further reading Gener
Page 239 and 240: 228 Chapter 10 B 1 - H + NH 3 CO
Page 241 and 242: 230 Chapter 10 ‘low-barrier’ +
Page 243 and 244: 232 Chapter 10 H S C 6 H 13 HN His
Page 245 and 246: 234 Chapter 10 O H NH 3 CO 2 − CO
Page 247 and 248: 236 Chapter 10 sub-units. Each sub-
Page 249 and 250: 238 Chapter 10 Further reading Gene
Page 251 and 252: 11 Radicals in Enzyme Catalysis 11.
Page 253 and 254:
242 Chapter 11 CH 2 Co III Ad H OH
Page 255 and 256:
244 Chapter 11 − O 2 C − O CO
Page 257 and 258:
246 Chapter 11 H N H O 734 H N H PF
Page 259 and 260:
248 Chapter 11 H H* + H + H 3 N CO
Page 261 and 262:
250 Chapter 11 O HN NH + H 3 N H 3
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252 Chapter 11 cofactor is involved
Page 265 and 266:
254 Chapter 11 Protein Radicals J.
Page 267 and 268:
256 Chapter 12 self-splicing reacti
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258 Chapter 12 Figure 12.2 Structur
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260 Chapter 12 antigen combining si
Page 273 and 274:
262 Chapter 12 R O OR' OH − R O
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264 Chapter 12 CO 2 − − O 2 C O
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266 Chapter 12 (1) Selective substr
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268 Chapter 12 HO O HO OH HO OH O O
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270 Chapter 12 Problems (1) How rev
Page 283 and 284:
Appendix 1: Cahn-Ingold-Prelog Rule
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Appendix 2: Amino Acid Abbreviation
Page 287 and 288:
276 Appendix 3 Preparation of orang
Page 289 and 290:
278 Appendix 4 (2) Intramolecular a
Page 291 and 292:
280 Appendix 4 from water at a-posi
Page 293 and 294:
282 Appendix 4 Chapter 8 (1) Treat
Page 295 and 296:
284 Appendix 4 (b) Formation of rad
Page 297 and 298:
286 Index b-hydroxydecanoyl thioest
Page 299 and 300:
288 Index glycosylation 26-7 glysop
Page 301 and 302:
290 Index phenylalanine ammonia lya
Page 303:
292 Index transition states 31-2 an
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