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Volumn 121, Issue 8, 1999, Pages 1636-1644

Resin-to-resin acyl- and aminoacyl-transfer reactions using oxime supports

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBAMIC ACID; IMIDAZOLE DERIVATIVE; OXIME; POLYMER; POLYSTYRENE; RESIN; UREA DERIVATIVE;

EID: 0033518862     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9818654     Document Type: Article
Times cited : (45)

References (63)
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    • Regen investigated triphase catalysis using solid supported catalysis with aqueous and organic layers. See: (a) Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956-5957. (b) Regen, S. L. J. Am. Chem. Soc. 1976, 98, 6270- 6274. (c) Regen, S. L. J. Org. Chem. 1977, 42, 875-879.
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    • Regen investigated triphase catalysis using solid supported catalysis with aqueous and organic layers. See: (a) Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956-5957. (b) Regen, S. L. J. Am. Chem. Soc. 1976, 98, 6270-6274. (c) Regen, S. L. J. Org. Chem. 1977, 42, 875-879.
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    • For phosphate transfer, see: (a) Rebek, J.; Gavina, F. J. Am. Chem. Soc. 1975, 97, 1591-1592. (b) Rebek, J.; Gavina, F. J. Am. Chem. Soc. 1975, 97, 3221-3222. (c) Rebek, J.; Gavina, F.; Navarro, C. Tetrahedron Lett. 1977, 35, 3021-3022. (d) Rebek, J.; Gavina, F.; Navarro, C. J. Am. Chem. Soc. 1978, 700, 8113-8117.
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    • Patchornik used resin-to-resin acyl transfer using o-nitrophenol resin with imidazole as an acyl group carrier. However, transferred groups were limited to N-protected monoamino acids. See: Patchornik, A. CHEMTECH 1987, 58-63.
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    • Patchornik published a multipolymer reaction for a preparative purpose. However, one of the resins acts as a base not a substrate. See: Cohen, B. J.; Kraus, M. A.; Patchornik, A. J. Am. Chem. Soc. 1977, 99, 4165-4167.
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    • Recently, Ouyang et al. published a two-resin system to generate small-molecule libraries. However, the second resin acts as a acid scavenger. See: Ouyang, X.; Armstrong, R. W.; Murphy, M. M. J. Org. Chem. 1998, 63, 1027-1032.
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    • unpublished results
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    • Part of the racemization might have occurred during the attachement of Boc-Phe onto oxime resin, as DMAP is known to cause racemization for the coupling between Boc-Phe anhydride and Wang resin. See: Atherton, E.; Benoiton, N. L.; Brown, E.; Sheppard, R. C.; Williams, B. J. Chem. Commun. 1981, 336-337.
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