Solid-phase synthesis of urea and amide libraries using the T2 triazene linker

Journal of Combinatorial Chemistry

Volumn 2, Issue 6, 2000, Pages 710-715

  Bräse, Stefan ^a   Dahmen, Stefan ^a   Pfefferkorn, Marc ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041025471     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000051s     Document Type: Article

References (32)

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18. Some recent syntheses: (a) Hamuro, Y.; Marshall, W. J.; Scialdone, M. A. Solid-Phase Synthesis of Acyclic and Cyclic Amino Acid Derived Urea Peptidomimetics using Phoxime Resin. J. Comb. Chem. 1999, 1, 163-172 and references therein,
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22. (c) Hodges, J. C.; Harikrishnan, L. S.; Ault-Justus, S. Preparation of Designer Resins via Living Free Radical Polymerization of Functional Monomers on Solid Support. J. Comb. Chem. 2000, 2, 80-88.
23. In general, every secondary or primary amine on solid phase could be used for this purpose.
24. Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Combinatorial Synthesis of Dihydropyridone Libraries and their Derivatives. Tetrahedron 1998, 54, 3983-3998.
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26. For a discussion using elemental analysis as quantification of loading, see: Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. Phosgenated p-Nitrophenyl(polystyrene)ketoxime or Phoxime resin. A New Resin for the Solid-Phase Synthesis of Ureas via Thermolytic Cleavage of Oxime-Carbamates. J. Org. Chem. 1998, 63, 4802-4807.
27. Dahmen, S.; Bräse, S. The First Stable Diazonium Ion on Solid Support-Investigations on Stability and Usage as Linker and Scavenger in Solid-Phase Organic Synthesis. Angew. Chem., Int. Ed. 2000, 39, 3681-3683; Angew. Chem. 2000, 112, 3827-3830.
28. Dahmen, S.; Bräse, S. The First Stable Diazonium Ion on Solid Support-Investigations on Stability and Usage as Linker and Scavenger in Solid-Phase Organic Synthesis. Angew. Chem., Int. Ed. 2000, 39, 3681-3683; Angew. Chem. 2000, 112, 3827-3830.
29. For solid-phase alkylation of amides: Nefzi, A.; Ostresh, J. M.; Meyer, J. P.; Houghten, R. A. Solid-Phase Synthesis of Heterocyclic Compounds from Linear Peptides: Cyclic Ureas and Thioureas. Tetrahedron Lett. 1997, 38, 931-934.
30. (a) The enantiomeric excess could not determined by means of HPLC methods.
31. (b) The coupling of free carboxylic acids under standard peptide coupling conditions is, in general, possible; however, the triazene nitrogen is less nucleophilic than a primary or secondary amine. Bräse, S.; Dahmen, S.; Pilot, C. Unpublished material.
32. Carvalho, E.; Iley J.; Rosa E. Kinetics and Mechanism of the Hydrolysis of Aminoacyltriazenes. J. Chem. Soc., Perkin Trans. 2 1998, 865-870 and references therein.