Library Science

A state-of-the-art collection of detailed synthetic procedures that lead to a variety of scaffolds, turn mimetics, peptide-bound replacements, and enzyme inhibitors. Topics range from unusual syntheses of amino acids to the use of a variety of linear and heterocyclic scaffolds in place of the peptide backbone. Important chemical procedures and methods include the transient protection of charged peptides as neutral prodrugs for improved blood-brain penetration and the replacement of peptide bonds with heterocyclic rings, olefins and fluoroolefins, and ketomethylenes. Synthetic protocols towards the transition-state mimics and reactive “warheads,” applicable in enzyme inhibitors, are also disclosed. Ed. Kazmierski, Wieslaw M

Table of Contents

1. Synthesis and Use of Pseudopeptides Derived from 1,2,4-Oxadiazole-, 1,3,4-0xadiazole-, and 1,2,4-Triazole-based Dipeptidomimetics (pp. 1-24)
   Luthman, Kristina; Borg, Susanna; Hacksell, Uli
2. Syntheses of FMOC-2,3-Methanoleucine Stereoisomers and Their Incorporation into Peptidomimetics (pp. 25-36)
   Burgess, Kevin; Li, Wen
3. Synthesis of an Esterase-Sensitive Cyclic Prodrug of a Model Hexapeptide Having Enhanced Membrane Permeability and Enzymatic Stability Using an Acyloxyalkoxy Promoiety (pp. 37-52)
   Gangwar, Sanjeev; Pauletti, Giovanni M.; Siahaan, Teruna J.; Stella, Valentino J.; Borchardt, Ronald T.
4. Synthesis of an Esterase-Sensitive Cyclic Prodrug of a Model Hexapeptide Having Enhanced Membrane Permeability and Enzymatic Stability Using a 3-(2???-Hydroxy-4???,6???-Dimethylphenyl)-3,3-Dimethyl Propionic Acid Promoiety (pp. 53-70)
   Wang, Binghe; Gangwar, Sanjeev; Pauletti, Giovanni; Siahaan, Teruna; Borchardt, Ronald T.
5. Synthesis of Coumarin-Based, Esterase-Sensitive Cyclic Prodrugs of Opioid Peptides with Enhanced Membrane Permeability and Enzymatic Stability (pp. 71-86)
   Wang, Binghe; Shan, Daxian; Wang, Wei; Zhang, Huijuan; Gudmundsson, Olafur; Borchardt, Ronald T.
6. Azatides as Peptidomimetics: Solution and Liquid Phase Syntheses (pp. 87-102)
   Han, Hyunsoo; Yoon, Juyoung; Janda, Kim D.
7. Synthesis of Cbz-Protected Ketomethylene Dipeptide lsosteres (pp. 103-124)
   Hoffman, Robert V.; Tao, Junhua
8. (E)-AIkene Peptide Bond lsosteres by Cuprate Opening of Vinyl Aziridines (pp. 125-136)
   Henninger, Todd C.; Wipf, Peter
9. Syntheses of Norstatine, Its Analogs, and Dipeptide lsosteres by Means of ?÷-Lactam Synthon Method (pp. 137-160)
   Ojima, lwao; Delaloge, Francette
10. Synthesis of a Versatile Peptidomimetic Scaffold (pp. 161-174)
    Hanessian, Stephen; McNaughton-Smith, Grant
11. An Asymmetric Synthesis Protocol to Prepare Topographically Constrained ?÷-Substituted Aromatic Amino Acids (pp. 175-188)
    Liao, Subo; Hruby, Victor J.
12. Synthesis of Oligopeptides Containing an Oxirane Ring in the Place of a Peptidic Bond (pp. 189-208)
    Taddei, Maurizio
13. Synthesis of Protected Lactam-Bridged Dipeptides (pp. 209-226)
    Perlow, Debra S.; Freidinger, Roger M.
14. Synthesis of Peptidomimics Through Sugar-Based Scaffolds (pp. 227-258)
    Le Merrer, Yves; Poitout, Lydie; Depezay, Jean-Claude
15. The Synthesis of Bicyclic Piperazinone and Related Derivatives (pp. 259-280)
    Fobian, Yvette M.; Moeller, Kevin D.
16. Synthesis of Dipeptides with ?[CH2O] Amide Bond Mimetics (pp. 281-292)
    Kazmierski, Wieslaw M.; Fritch, Paul C.
17. SNAr-Based Cycloetherification Methodology: Application in the Synthesis of Heterodectic Macrocyclic Peptides with Endo Aryl-Aryl and Aryl-Alkyl Ether Bonds (pp. 293-320)
    Zhu, Jieping
18. Cyclic Aromatic Amino Acids with Constrained x1 and x2 Dihedral Angles (pp. 321-338)
    Tourwe, Dirk; Iterbeke, Koen; Kazmierski, Wieslaw M.; Toth, Geza
19. Asymmetric Syntheses of Unnatural Amino Acids and Hydroxyethylene Peptide lsosteres (pp. 339-356)
    Williams, Robert M.
20. Fluoroolefin lsosteres (pp. 357-384)
    Welch, J. T.; Allmendinger, T.
21. Synthesis of 3-Amino-1-Carboxymethyl- Benzodiazepine (BZA) Peptidomimetics (pp. 385-396)
    Marsters, James C.; Rawson, Thomas E.
22. A Conformationally Restricted ?÷-Strand HIV Protease Inhibitor (pp. 397-406)
    Hillier, Michael C.; Martin, Stephen F.
23. Synthesis of Cyclopropane-Containing Leu-Enkephalin Analogs (pp. 407-416)
    Dwyer, Michael P.; Martin, Stephen F.
24. The 1,5-Disubstituted Tetrazole Ring as a cis-Amide Bond Surrogate (pp. 417-436)
    Zabrocki, Janusz; Marshall, Garland R.
25. Synthesis of (2R, 3R, 4R, 5S)-5-tert- Butyloxycarbonylamino-3,4-Dihydroxy-2-lsopropyl- 3,4-O,O-lsopropylidene-6-Cyclohexyl-Hexanoic Acid (pp. 437-452)
    Scott, Allen; Conway, Brian G.; Krook, Mark A.
26. Synthesis of (2S,4S,5S)-5-(t-Butoxycarbonylamino)- 4-(t-Butyldimethylsilyloxy)-2-lsopropyl- 7-Methyl Octanoic Acid (pp. 453-466)
    Lyster, Mark A.; Conway, Brian G.
27. Synthesis of a-Vinyl Amino Acids (pp. 467-488)
    Berkowitz, David B.; McFadden, Jill M.; Smith, Marianne K.; Pedersen, Michelle L.
28. A Novel Synthetic Protocol for the Preparation of Enantiopure 3-,4-, and 5-Substituted Prolines (pp. 489-512)
    Sasaki, N. Andre
29. Synthesis of Aminobenzoic Acid-Based Nonpeptide Templates: Applications in Peptidomimetic Drug Discovery (pp. 513-526)
    Para, Kimberly S.; Sawyer, Tomi K.
30. Aminimides as Peptidomimetics (pp. 527-538)
    Fulton, Brian S.; Kaplan, Alan P.; Hogan, Joseph C.; Gallion, Steven L.

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