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1H NMR studies in polar solvents such as DMSO do not provide evidence for intramolecular H-bonding. The fact that we have found the pyrrolinones to be inhibitors of proteases (e.g., renin and HIV-1 protease), however, suggests that they can adopt a β-strand conformation in water.
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19. The 1987 version of the MM2 force field was used: Bowen, J. P.; Pathiaseril, A.; Profeta, Jr. S.; Allinger, N. L. J. Org. Chem. 1987, 52, 5162. See also: Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
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19. The 1987 version of the MM2 force field was used: Bowen, J. P.; Pathiaseril, A.; Profeta, Jr. S.; Allinger, N. L. J. Org. Chem. 1987, 52, 5162. See also: Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
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20. Miller, M.; Schneider, J.; Sathyanarayana, B. K.; Toth, M. V.; Marshall, G. R.; Clawson, L.; Selk, L. M.; Kent, S. B. H.; Wlodawer, A. Science 1989, 246, 1149. Swain, A. L.; Miller, M. M.; Green, J.; Rich, D. H.; Schneider, J.; Kent, S. B. H.; Wlodawer, A. Proc. Nad Acad. Sci. U.S.A. 1990, 87, 8805.
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Kent, S.B.H.8
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46
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20. Miller, M.; Schneider, J.; Sathyanarayana, B. K.; Toth, M. V.; Marshall, G. R.; Clawson, L.; Selk, L. M.; Kent, S. B. H.; Wlodawer, A. Science 1989, 246, 1149. Swain, A. L.; Miller, M. M.; Green, J.; Rich, D. H.; Schneider, J.; Kent, S. B. H.; Wlodawer, A. Proc. Nad Acad. Sci. U.S.A. 1990, 87, 8805.
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47
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84988057355
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21. The aldol-oxidation protocol is one of the best ways to prepare 1,3-diketones: Smith, III, A. B.; Levenberg, P. A. Synthesis 1981, 567.
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84956106373
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22. (a) Seebach, D.; Fadel, A. Helv. Chim. Acta. 1985, 68, 1243. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta. 1987, 70, 1194.
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Seebach, D.1
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84987557280
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22. (a) Seebach, D.; Fadel, A. Helv. Chim. Acta. 1985, 68, 1243. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta. 1987, 70, 1194.
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Seebach, D.1
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50
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0000215530
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(b) Karady, S.; Amato, J. S.; Weinstock, L. M. Tetrahedron Lett. 1984, 25, 4337. Amato, J. S.; Weinstock, L. M.; Karady, S. U.S. Patent 4 508 921, 1985.
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0000215530
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U.S. Patent 4 508 921, 1985
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(b) Karady, S.; Amato, J. S.; Weinstock, L. M. Tetrahedron Lett. 1984, 25, 4337. Amato, J. S.; Weinstock, L. M.; Karady, S. U.S. Patent 4 508 921, 1985.
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Amato, J.S.1
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84953502363
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23. Levin, J. I.; Turos, E.; Weinreb, S. M. Syn. Commun. 1982, 12, 989.
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Levin, J.I.1
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53
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85015356069
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24. Olah, G. A.; Masatomo, N.; Kerekes, I. Synthesis 1973, 487. Acid fluorides were chosen as intermediates due to the known facile rearrangement of urethane-protected α-amino acid chlorides to their corresponding N-carboxy (Leuchs) anhydrides: Carpino, L. A.; Mansour, E.-S. M. E.; SadatAalaee, D. J. Org. Chem. 1991, 56, 2611.
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Olah, G.A.1
Masatomo, N.2
Kerekes, I.3
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54
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33751498929
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24. Olah, G. A.; Masatomo, N.; Kerekes, I. Synthesis 1973, 487. Acid fluorides were chosen as intermediates due to the known facile rearrangement of urethane-protected α-amino acid chlorides to their corresponding N-carboxy (Leuchs) anhydrides: Carpino, L. A.; Mansour, E.-S. M. E.; SadatAalaee, D. J. Org. Chem. 1991, 56, 2611.
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Carpino, L.A.1
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55
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0014064928
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25. Konopinska, D.; Siemion, I. Z. Angew. Chem., Int. Ed. Engl. 1967, 6, 248.
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Konopinska, D.1
Siemion, I.Z.2
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56
-
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0025012066
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26. For background information on urethane-protected amino acid N-carboxy anhydrides, see: Fuller, W. D.; Cohen, M. P.; Shabankareh, M.; Blair, R. K.; Goodman, M.; Naider, F. R. J. Am. Chem. Soc. 1990, 112, 7414.
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Fuller, W.D.1
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Goodman, M.5
Naider, F.R.6
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59
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0027931547
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29. Concurrant to our investigations, Hecht reported the preparation of a 2,5-disubstituted pyrrolinone, via a Hg(II) mediated cyclization, as an intermediate in the synthesis of (+)-preussin: Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721.
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Overhand, M.1
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64
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0029995939
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34. Nagamitsu, T.; Sunazuka, T.; Tanaka, H; Ōmura, S.; Sprengeler, P. A.; Smith, III A. B. J. Am. Chem. Soc., 1996, 118, 3548.
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Nagamitsu, T.1
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Sprengeler, P.A.5
Smith A.B. III6
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65
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33845551037
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35. Still, W. C.; Murata, S.; Revial, G.; Yosihara, K. J. Am. Chem. Soc. 1983, 705, 625.
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Still, W.C.1
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66
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85030291554
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note
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36. Compounds of this type in which the aldehyde is flanked by an iso-butyl group (derived from leucine) are also more stable than aldehyde 42, but are not as robust as 55. This is presumably due to the added steric bulk of the iso-propyl group of aldehyde 55, rendering it much less susceptible to nucleophilic attack.
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