New methodology for high throughput solution-phase synthesis: Affinity purification by using crown ether and ammonium ion interaction

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7479-7483

  Zhang, San qi ^a   Fukase, Koichi ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Affinity purification; Ammonium ion; Combinatorial chemistry; Crown ether; High throughput synthesis

Indexed keywords

AMMONIA; CROWN ETHER; HETEROCYCLIC COMPOUND; PEPTIDE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL INTERACTION; METHODOLOGY; PURIFICATION; SYNTHESIS;

EID: 0033570055     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01507-5     Document Type: Article

References (18)

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2. (a) Janknecht, R.; Nordheim, A. Gene 1992, 121, 321. (b) Zhao, L. J.; Narayan, O. Gene 1993, 137, 345. (c) Schmidt, J.; Hess, H.; Stunnenberg, H. G. Mol. Biol. Rep. 1993, 18, 223.
3. (a) Janknecht, R.; Nordheim, A. Gene 1992, 121, 321. (b) Zhao, L. J.; Narayan, O. Gene 1993, 137, 345. (c) Schmidt, J.; Hess, H.; Stunnenberg, H. G. Mol. Biol. Rep. 1993, 18, 223.
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6. Ramage developed a new method of purification by the use of the affinity of tetrabenzo[a,c,g,i]fluorene to charcoal: (a) Ramage, R.; Swenson, H. R.; Shaw, K. T. Tetrahedron Lett. 1998, 39, 8715. (b) Hay, A. M.; Hobbs-Dewitt, S.; MacDonald, A. A.; Ramage, R. Tetrahedron Lett. 1998, 39, 8721.
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11. The affinity of smaller crown ethers such as 5-methoxycarbonyl-1,3-phenylene-16-crown-5 or dibenzo-24-crown-8 with the aminomethylated resin (TFA form) was not strong enough to retain substrates in the column.
12. 2 acetic acid form but was retained in that of the formic acid form. TFA is, however, more effective.
13. Commercially available from Argonaut Technologies, San Carlos, California: http://www.argotech.com.
14. 2 after each cycle.
15. 2 (1:1). Evaporation of the solvents afforded 17 with high purity.
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17. Solid-phase synthesis of aryl and benzylpiperazines: Dankwardt, S. M.; Newman, S. R.; Krstenansky, J. L. Tetrahedron Lett. 1995, 36, 4923. In the case of the solid-phase aromatic substitution, it took 48 h at rt to complete the reaction of the polymer-supported fluoronitrobenzene with 1-phenylpiperazine (10 equiv.).
18. For a polymer-supported solution synthesis of arylpiperazines, see: Pan, P.-C.; Sun, C.-M. Tetrahedron Lett. 1998, 39, 9505.