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4
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84987566762
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Abbreviations for AmAbz derivatives are constructed according to the recommendations of the IUPAC-IUB Commission on Biochemical Nomenclature (Eur. J. Biochem. 1984, 138, 9-37), 4-amino and 3-aminomethyl groups being defined as main-chain and side-chain groups, respectively. Additional abbreviations used are: - Boc: tert-butyloxycarbonyl; BOP: benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate; DIC: N,N′-diisopropylcarbodiimide; DMF: N,N-dimethylformamide; DIEA: N-ethyldiisopropylamine; HOBt: N-hydroxybenzotriazole; Pht: phthaloyl; OSu: succinimidyloxy; TFA: trifiuoroacetic acid.
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33847559167
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(Ed.: W. M. Kazmierski), Humana Press Inc., Totowa, NJ
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For examples of dipeptide mimics based on amino or aminoalkyl benzoic acid, see K. S. Para, T. K. Sawyer, in: Methods in Molecular Medicine, Vol. 23: Peptidomimetics Protocols (Ed.: W. M. Kazmierski), Humana Press Inc., Totowa, NJ, 1999, pp. 513-526.
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Para, K.S.1
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0029621159
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[7b] W. H. Miller, T. W. Ku, F. E. Ali, W. E. Bondinell, R. R. Calvo, L. D. Davis, K. F. Erhard, L. B. Hall, W. F. Huffman, R. M. Keenan, C. Kwon, K. A. Newlander, S. T. Ross, J. M. Samanen, D. T. Takata, C.-K. Yuan, Tetrahedron Lett. 1995, 36, 9433-9436. -
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Kwon, C.11
Newlander, K.A.12
Ross, S.T.13
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Takata, D.T.15
Yuan, C.-K.16
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9
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0029013404
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[7c] T. W. Ku, W. H. Miller, W. E. Bondinell, K. F. Erhard, R. M. Keenan, A. J. Nichols, C. E. Peishoff, J. M. Samanen, A. S. Wong, W. F. Huffman, J. Med. Chem. 1995, 38, 9-12. -
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33847572610
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German Patent 73-2318636 (1973)
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[7d] J. Keck, H. Pieper, G. Krueger, S. Pueschmann, K. R. Noll, German Patent 73-2318636 (1973); Chem. Abstr. 1975, 82, 98715.
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Keck, J.1
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12
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0023805116
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H. Ogawa, S. Tamada, T. Fujioka, S. Teramoto, K. Kondo, S. Yamashita, Y. Yabuuchi, M. Tominaea, K. Nakaeawa, Chem. Pharm. Bull. 1988, 36, 2253-2258.
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Ogawa, H.1
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16
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0003033095
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Ed.: J. Zabicky, Interscience Publishers, London
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R. B. Homer, C. D. Johnson, in: The Chemistry of Amides (Ed.: J. Zabicky), Interscience Publishers, London, 1970; pp. 187-245.
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Homer, R.B.1
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85004775207
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D. R. Bolin, I.-I. Sytwu, F. Humiec, J. Meienhofer, Int. J. Pept. Protein Res. 1989, 33, 353-359 and references therein.
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18
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0003592999
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Butterworths, London
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G. Kortüm, W. Vogel, K. Andrussow, Dissociation Constants of Organic Acids in Aqueous Solution, Butterworths, London, 1961, p. 381.
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Kortüm, G.1
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15144343348
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P. Chand, Y. S. Babu, S. Bantia, N. Chu, L. B. Cole, P. L. Kotian, W. G. Laver, J. A. Montgomery, V. P. Pathak, S. L. Petty, D. P. Shrout, D. A. Walsh, G. M. Walsh, J. Med. Chem. 1997, 40, 4030-4052.
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Walsh, G.M.13
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21
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33847561258
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-
note
-
In preliminary experiments, acid hydrolysis turned out to be impracticable due to a very sluggish process even in hot concentrated acid.
-
-
-
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22
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0033537963
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-
S. Papot, C. Bachmann, D. Combaud, J.-P. Gesson, Tetrahedron 1999, 55, 4699-4708.
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Papot, S.1
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Gesson, J.-P.4
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23
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33847543722
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-
note
-
Prior conversion of carboxyl group into methyl ester was achieved in order to avoid any side reaction with carbonyldiimidazole.
-
-
-
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24
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85088004859
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note
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[9]
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-
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27
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0001275595
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[23b] M. S. Bernatowicz, S. B. Daniels, H. Köster, Tetrahedron Lett. 1989, 30, 4645-4648.
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Bernatowicz, M.S.1
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28
-
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85088005525
-
-
note
-
2 to give peptide resin 12, solvent (DCM or DMF) was added 5 min after carbodiimide addition for technical reasons (gelation of the reaction medium, probably due to precipitation of Fmoc-Phe symmetrical anhydride).
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-
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29
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0025868658
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J. Coste, E. Frerot, P. Jouin, B. Castro, Tetrahedron Lett. 1991, 32, 1967-1970.
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30
-
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85088005236
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note
-
[6]).
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31
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85088005618
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note
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2.
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32
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33947338256
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-
An explanation of this efficiency is that the effective acylating species may be the initially formed O-acylisourea intermediate, since the arylamine is a stronger nucleophile than neutral carboxylic acid and, thus, acylation may have occurred before the symmetrical anhydride had formed. This interpretation is consistent with the proposal of direct formation of acylpyridinium from O-acylisourea and pyridine (D. F. DeTar, R. Silverstein, J. Am. Chem. Soc. 1966, 88, 1020-1023). In addition, since the poorly nucleophilic arylamino group of AmAbz is not protonated in the medium, it is able to react in the absence of base.
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DeTar, D.F.1
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33
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33847558295
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(Ed.: K. Brunfeldt), Scriptor, Copenhagen
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H. S. Bates, J. H. Jones, W. I. Ramage, M. J. Witty, in: Peptides 1980. Proc. 16th Eur. Pept. Symp. (Ed.: K. Brunfeldt), Scriptor, Copenhagen, 1981, pp. 185-190.
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37049081496
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R. Sola, P. Saguer, M. L. David, R. Pascal, J. Chem. Soc., Chem. Commun. 1993, 1786-1788.
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0028000462
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R. Pascal, D. Chauvey, R. Sola, Tetrahedron Lett. 1994, 34, 6291-6294.
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Pascal, R.1
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