A novel method for the determination of isokinetic ratios and its application in the synthesis of two new positional scanning libraries

ACS Combinatorial Science

Volumn 14, Issue 9, 2012, Pages 503-512

  Giulianotti, Marc A ^a   Debevec, Ginamarie ^a   Santos, Radleigh G ^a   Maida, Laura E ^a   Chen, Wenteng ^a,b   Ou, Lili ^a,b   Yu, Yongping ^a,b   Dooley, Colette T ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

combinatorial libraries; guanidine; harmonic mean; isokinetic ratios; piperazine; positional scanning library; sulfonamide

Indexed keywords

PEPTIDE FRAGMENT; PIPERAZINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; MOLECULAR LIBRARY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; PEPTIDE FRAGMENTS; PIPERAZINES; SMALL MOLECULE LIBRARIES; SULFONAMIDES;

EID: 84866095427     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300060s     Document Type: Article

References (20)

1. Dolle, R. E.; Bourdonnex, B. L.; Worm, K.; Morales, G. A.; Thomas, C. J.; Zhang, W. Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009 J. Comb. Chem. 2010, 12, 765-806
2. Houghten, R. A.; Pinilla, C.; Giulianotti, M. A.; Appel, J. R.; Dooley, C. T.; Ostresh, J. M.; Yu, Y.; Maggiora, G. M.; Medina-Franco, J. L.; Brunner, D.; Schneider, J. Strategies for the Use of Mixture-Based Synthetic Combinatorial Libraries: Scaffold Ranking, Direct Testing In Vivo, and Enhanced Deconvolution by Computational Methods J. Comb. Chem. 2008, 10, 3-19
3. Pinilla, C.; Appel, J. R.; Borràs, E.; Houghten, R. A. Advances in the Use of Synthetic Combinatorial Chemistry: Mixture-Based Libraries Nat. Med. 2003, 9, 118-122 (Pubitemid 36098272)
4. Reilley, K. J.; Giulianotti, M.; Dooley, C. T.; Nefzi, A.; McLaughlin, J. P.; Houghten, R. H. Identification of Two Novel, Potent, Low-Liability Antinociceptive Compounds from the Direct In Vivo Screening of a Large Mixture-Based Combinatorial Library AAPS J. 2010, 12, 318-329
5. Judkowski, V.; Bunying, A.; Ge, F.; Appel, J. R.; Law, K.; Sharma, A.; Raja-Gabaglia, C.; Norori, P.; Santos, R. G.; Giulianotti, M. A.; Slifka, M. K.; Douek, D. C.; Graham, B. S.; Pinilla, C. GM-CSF Production Allows the Identification of Immunoprevalent Antigens Recognized by Human CD4 + T Cells Following Smallpox Vaccination PLoS One 2011, 6 (9 e24091
6. Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Generation and Use of Synthetic Peptide Combinatorial Libraries for Basic Research and Drug Discovery Nature 1991, 354, 84-86 (Pubitemid 21896788)
7. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity Nature 1991, 354, 82-84 (Pubitemid 21896787)
8. Furka, A.; Sebestye, F.; Asgedom, M.; Dibo, G. General Method for Rapid Synthesis of Multicomponent Peptide Mixtures Int. J. Peptide Protein Res. 1991, 37, 487-493
9. Ostresh, J. M.; Winkle, J. H.; Hamashin, V. T.; Houghten, R. A. Peptide Libraries: Determination of Relative Reaction Rates of Protected Amino Acids in Competitive Couplings Biopolymers 1994, 34, 1681-1689 (Pubitemid 24357583)
10. Ljungdahl, T.; Veide-Vilg, J.; Wallner, F.; Tamas, M. J.; Grtli, M. Positional Scanning Peptide Libraries for Kinase Substrate Specificity Determinations: Straightforward and Reproducible Synthesis Using Pentafluorophenyl Esters J. Comb. Chem. 2010, 12, 733-742
11. Acharya, A. N; Ostresh, J. M.; Houghten, R. A. Determination of Isokinetic Ratios Necessary for Equimolar Incorporation of Carboxylic Acids in the Solid-Phase Synthesis of Mixture-Based Combinatorial Libraries Biopolymers 2002, 65, 32-39 (Pubitemid 35000891)
12. Dombi, K. L; Steiner, U. E.; Richert, C. Rapidly Measuring Reactivities of Carboxylic Acids to Generate Equireactive Building Block Mixtures: A Spectrometric Assay J. Comb. Chem. 2003, 5, 45-60 (Pubitemid 37130450)
13. Ostresh, J. M.; Schoner, C.; Giulianotti, M.; Kurth, M.; Dörner, B.; Houghten, R. Combinatorial Libraries: Equimolar Incorporation of Benzaldehyde Mixtures in Reductive Alkylation Reactions Pept. Proc. Am. Pept. Symp. 2002, 5, 57-58
14. Nefzi, A.; Ostresh, J. M.; Yu, J.; Houghten, R. A. Combinatorial Chemistry: Libraries from Libraries, the Art of the Diversity-Oriented Transformation of Resin-Bound Peptides and Chiral Polyamides to Low Molecular Weight Acyclic and Heterocyclic Compounds J. Org. Chem. 2004, 69, 3603-3609 (Pubitemid 38668216)
15. 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, 931-914
16. Houghten, R. A. General Method for the Rapid Solid-Phase Synthesis of Large Numbers of Peptides: Specificity of Antigen-Antibody Interaction at the Level of Individual Amino Acids Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 5131-5135 (Pubitemid 16242814)
17. Boutin, J. A.; Gesson, I.; Menlin, J.-M.; Bertin, S.; Lambert, P.-H.; Volland, J.-P.; Fauchere, J.-L. Limitations of the Coupling of Amino Acid Mixtures for the Preparation of Equimolar Peptide Libraries Mol. Diversity 1997, 3, 43-60 (Pubitemid 127508357)
18. Appel, M. J.; LaBarre, R; Radulović, D. On Accelerated Random Search, SIAM J. Optim. 2003, 14, 708-731
19. Santos, R. G.; Giulianotti, M. A.; Dooley, C. T.; Pinilla, C.; Appel, J. R.; Houghten, R. A. Use and Implications of the Harmonic Mean Model on Mixtures for Basic Research and Drug Discovery ACS Comb. Sci. 2011, 13, 337-344
20. Nefzi, A.; Mimna, R. A.; Houghten, R. A. Parallel Solid-Phase Synthesis of Disubstituted 1,6-Piperazine-2-ones J. Comb. Chem. 2002, 4, 542-545