Thermographic selection of effective catalysts from an encoded polymer- bound library

Science

Volumn 280, Issue 5361, 1998, Pages 267-270

  Taylor, Steven J ^a   Morken, James P ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ORGANIC POLYMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL); TEMPERATURE; THERMOGRAPHY (IMAGING);

ACYLATION REACTION; ENCODED POLYMER BOUND LIBRARY; MULTIFUNCTIONAL CATALYST; THERMOGRAPHIC SELECTION;

CATALYSTS;

CHLOROFORM; POLYMER; SOLVENT;

ARTICLE; CAMERA; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; INFRARED PHOTOGRAPHY; KINETICS; POLYMERIZATION; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; THERMOGRAPHY;

EID: 0032502884     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.280.5361.267     Document Type: Article

References (34)

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25. For relevant studies, see E. J. Delaney, L. E. Wood, I. M. Klotz, J. Am. Chem. Soc. 104, 799 (1982); M. Tomoi, Y. Akada, H. Kakiuchi, Makromol. Chem. Rapid Commun. 3, 537 (1982); F. M. Menger and D. J. McCann, J. Org. Chem. 50, 3928 (1985); A. Deratani, G. D. Darling, D. Horak, J. M. J. Frechet, Macromolecules 20, 767 (1987).
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29. Library synthesis was performed on aminomethyl polystyrene macrobeads (500 μm, 1.04 mmol/g; Rapp Polymere, Tübingen, Germany), because catalysts on this polymer support were found to give a larger temperature increase in a related assay developed in our labs.
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31. B12 was prepared by treatment of L-proline fertbutyl ester (2 equiv.) and 4-bromopyridine (1 equiv.) with diisopropylethylamine (3 equiv) in dimethyl sulfoxide at 120°C for 12 hours.
32. Synthesis efficiency or site-site interactions between multiple catalyst moieties may lead to variation in observed activity that does not reflect inherent activity. In regard to catalyst synthesis, preliminary data indicate that the syntheses were successful in the preparation of 1, 2, and 5. Catalyst resynthesis on Rink amide resin (Novabiochem) followed by cleavage from solid support afforded a compound with very clean low-resolution fast atom bombardment mass spectra corresponding to the predicted product in each case. Although these results are not quantitative and are somewhat ambiguous because a different resin was used in resynthesis as compared with library preparation, they do indicate that no fundamental synthesis problems occurred during the preparation of these monomer sequences.
33. J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds (Academic Press, New York, 1970).
34. We thank L. H. Bogart of Cincinnati Electronics (Mason, OH) and R. E. Richardson of Mec-Tric Control (Charlotte, NC) for assistance and use of the Cincinnati Electronics IRRIS-256ST IR camera.