ACS Combinatorial Science
RESEARCH ARTICLE
’ ACKNOWLEDGMENT
Nature 1991, 354, 84–86. (d) Lam, K. S.; Lebl, M.; Krchnak, V. The
“One-Bead-One-Compound” Combinatorial Library Method. Chem.
Rev. 1997, 97, 411–448.
This work was supported financially by the University of
Berne, the Swiss National Science Foundation, and the Marie
Curie Training Network IBAAC.
(7) (a) Clouet, A.; Darbre, T.; Reymond, J.-L. A Combinatorial
Approach to Catalytic Peptide Dendrimers. Angew. Chem., Int. Ed. 2004,
43, 4612–4615. (b) Maillard, N.; Clouet, A.; Darbre, T.; Reymond, J.-L.
Combinatorial Libraries of Peptide Dendrimers: Design, Synthesis, On-
Bead High-Throughput Screening, Bead Decoding and Characteriza-
tion. Nat. Protoc. 2009, 4, 132–142. (c) Javor, S.; Delort, E.; Darbre, T.;
Reymond, J.-L. Peptide Dendrimer Enzyme Model with a Single
Catalytic Site at the Core. J. Am. Chem. Soc. 2007, 129, 13238–13246.
(8) Kofoed, J.; Darbre, T.; Reymond, J.-L. Artificial aldolases from
peptide dendrimer combinatorial libraries. Org. Biomol. Chem.
2006, 3268–3281.
(9) Uhlich, N. A.; Sommer, P.; B€uhr, C.; Sch€urch, S.; Reymond, J.-L.;
Darbre, T. Remote Control of Bipyridine-Metal Coordination with a
Peptide Dendrimer. Chem. Commun. 2009, 6237–6239.
(10) (a) Sommer, P.; Uhlich, N. A.; Reymond, J.-L.; Darbre, T. A.
Peptide Dendrimer Model for Vitamin B12 Transport Proteins. Chem-
BioChem 2008, 9, 689–693. (b) Uhlich, N.; Natalello, A.; Kadam, R. U.;
Doglia, S. M.; Reymond, J.-L.; Darbre, T. Structure and Binding of
Peptide Dendrimer Ligands to Vitamin B12. ChemBioChem 2010,
11, 358–365.
(11) (a) Kolomiets, E.; Johansson, E. M. V.; Renaudet, O.; Darbre,
T.; Reymond, J.-L. Neoglycopeptide Dendrimer Libraries as a Source of
Lectin Binding Ligands. Org. Lett. 2007, 9, 1465–1468. (b) Kolomiets,
E.; Swiderska, M. A.; Kadam., R. U.; Johansson, E. M. V.; Jaeger, K.-E.;
Darbre, T.; Reymond, J.-L. Glycopeptide dendrimers with high affinity
for the fucose binding lectin PA-IIL from Pseudomonas Aeruginosa.
ChemMedChem 2009, 4, 562–569.
(12) Maillard, N.; Darbre, T.; Reymond, J.-L. Identification of
Catalytic Peptide Dendrimers by “Off-Bead” in Silica High-Throughput
Screening of Combinatorial Libraries. J. Comb. Chem. 2009,
11, 667–675.
’ REFERENCES
(1) (a) Newkome, G. R.; Moorefield, C. N.; V€ogtle, F. Dendritic
Molecules: Concepts, Synthesis, Applications; VCH: Weinheim, 2001;
(b) Kofoed, J.; Reymond, J.-L. Dendrimers as artificial enzymes. Curr.
Opin. Chem. Biol. 2005, 9, 656–664. (c) Lee, C. C.; MacKay, J. A.; Frechet,
J. M. J.; Szoka, F. C. Designing dendrimers for biological applications. Nat.
Biotechnol. 2005, 23, 1517–1526. (d) Astruc, D.; Boisselier, E.; Ornelas, C.
Dendrimers Designed for Functions: From Physical, Photophysical, and
Supramolecular Properties to Applications in Sensing, Catalysis, Molecular
Electronics, Photonics, and Nanomedicine. Chem. Rev. 2010, 110,
1857–1959.
(2) (a) Kreiter, R.; Kleij, A. W.; Klein Gebbink, R. J. M.; van Koten,
G. Dendritic Catalysts. In Topics in Current Chemistry; Springer-Verlag:
Berlin, 2001; Vol. 217, pp 163ꢀ199. (b) Garcia-Martinez, J. C.;
Lezutekong, R.; Crooks, R. M. Dendrimer-Encapsulated Pd Nanopar-
ticles as Aqueous, Room-Temperature Catalysts for the Stille Reaction.
J. Am. Chem. Soc. 2005, 127, 5097–5103. (c) Lu, S. M.; Alper, H.
Intramolecular Carbonylation Reactions with Recyclable Palladium-
Complexed Dendrimers on Silica: Synthesis of Oxygen, Nitrogen, or
Sulfur-Containing Medium Ring Fused Heterocycles. J. Am. Chem. Soc.
2005, 127, 14776–14784. (d) Tang, W.-J.; Yang, N.-F.; Yi, B.; Deng, G.-
J.; Huang, Y.-Y.; Fan, Q.-H. Phase selectively soluble dendrimer-bound
osmium complex: a highly effective and easily recyclable catalyst for
olefin dihydroxylation. Chem. Commun. 2004, 1378–1379. (e) Liang,
C. O.; Helms, B.; Craig, J.; Frechet, J. M. J. Dendronized cyclocopoly-
mers with a radial gradient of polarity and their use to catalyze a difficult
esterification. Chem. Commun. 2003, 2524–2525.
(13) (a) Kofoed, J.; Nielsen, J.; Reymond, J.-L. Discovery of New
Peptide-based Catalysts for the Direct Asymmetric Aldol Reaction.
Bioorg. Med. Chem. Lett. 2003, 13, 2445–2447. (b) Martin, H. J.; List,
B. Mining sequence space for asymmetric aminocatalysis. N-Terminal
prolylpeptides efficiently catalyze enantioselective aldol and Michael
reactions. Synlett 2003, 1901–1902. (c) Tang, Z.; Yang, Z.-H.; Cun, L.-
F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Small Peptides Catalyze Highly
Enantioselective Direct Aldol Reactions of Aldehydes with Hydroxya-
cetone: Unprecedented Regiocontrol in Aqueous Media. Org. Lett.
2004, 6, 2285–2287. (d) Notz, W.; List, B. Catalytic Asymmetric
Synthesis of anti-1,2-Diols. J. Am. Chem. Soc. 2000, 122, 7386–7387.
(e) Shi, L.-X.; Sun, Q.; Ge, Krattiger, P.; Kovasy, R.; Revell, J. D.; Ivan, S.;
Wennemers, H. Increased structural complexity leads to higher activity:
peptides as efficient and versatile catalysts for asymmetric aldol reac-
tions. Org. Lett. 2005, 7, 1101–1103.
(14) (a) Kofoed, J.; Reymond, J. L. A general method for designing
combinatorial peptide libraries decodable by amino acid analysis.
J. Comb. Chem. 2007, 9, 1046–52. (b) Kofoed, J.; Reymond, J. L.
Identification of protease substrates by combinatorial profiling on
TentaGel beads. Chem. Commun. 2007, 4453–4455. (c) Fluxa, V. S.;
Reymond, J. L. On-bead cyclization in a combinatorial library of 15,625
octapeptides. Bioorg. Med. Chem. 2009, 17, 1018–1025. (d) Dulery, V.;
Uhlich, N. A.; Maillard, N.; Fluxa, V. S.; Garcia, J.; Dumy, P.; Renaudet,
O.; Reymond, J. L.; Darbre, T. A cyclodecapeptide ligand to vitamin B12.
Org. Biomol. Chem. 2008, 6, 4134–4141. (e) Fluxa, V. S.; Maillard, N.;
Page, M. G.; Reymond, J. L. Bead diffusion assay for discovering
antimicrobial cyclic peptides. Chem. Commun. 2011, 1434–1436.
(15) Biswas, R.; Maillard, N.; Kofoed, J.; Reymond, J.-L. Comparing
dendritic with linear esterase peptides by screening SPOT arrays for
catalysis. Chem. Commun. 2010, 8746–8748.
(3) (a) Esposito, A.; Delort, E.; Lagnoux, D.; Djojo, F.; Reymond, J.-
L. Catalytic Peptide Dendrimers. Angew. Chem., Int. Ed. 2003,
42, 1381–1383. (b) Douat-Casassus, C.; Darbre, T.; Reymond, J.-L.
Selective Catalysis with Peptide Dendrimers. J. Am. Chem. Soc. 2004,
126, 7817–7826. (c) Delort, E.; Darbre, T.; Reymond, J.-L. A Strong
Positive Dendritic Effect in a Peptide Dendrimer-Catalyzed Ester
Hydrolysis Reaction. J. Am. Chem. Soc. 2004, 126, 15642–15643.
(d) Delort, E.; Nguyen-Trung, N.-Q.; Darbre, T.; Reymond, J.-L. Synthesis
and Activity of Histidine Containing Catalytic Peptide Dendrimers.
J. Org. Chem. 2006, 71, 4468–4480. (e) Darbre, T.; Reymond, J.-L.
Peptide Dendrimers as Artificial Enzymes, Receptors, and Drug-Delivery
Agents. Acc. Chem. Res. 2006, 39, 925–934.
(4) (a) Berkessel, A.; Herault, D. A. Discovery of peptide-zirconium
complexes that mediate phosphate hydrolysis by batch screening of a
combinatorial undecapeptide library. Angew. Chem., Int. Ed. 1999,
38, 102–105. (b) Copeland, G. T.; Miller, S. J. Selection of enantiose-
lective acyl transfer catalysts from a pooled peptide library through a
fluorescence-based activity assay. An approach to kinetic resolution of
secondary alcohols of broad structural scope. J. Am. Chem. Soc. 2001,
113, 6496–6502.
(5) (a) Krattiger, P.; McCarthy, C.; Pfaltz, A.; Wennemers, H.
Catalyst-Substrate Coimmobilization. A Strategy for Catalysts Discov-
ery in Split.and.Mix Libraries. Angew. Chem., Int. Ed. 2003,
42, 1722–1724. (b) Bauke-Albada, H.; Liskamp, R. M. J. TAC-Scaf-
folded Tripeptides as Artificial Hydrolytic Receptors. A Combinatorial
Approach Toward Esterase Mimics. J. Comb. Chem. 2008, 10, 814–824.
(6) (a) Furka, A.; Sebestyꢀen, F.; Asgedom, M.; Dibꢀo, G. General
method for rapid synthesis of multicomponent peptide mixtures. Int. J.
Pept. Protein Res. 1991, 37, 487–493. (b) 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. (c) 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.
(16) Yang, Y.; Babiak, P.; Reymond, J.-L. New Monofunctionalized
Fluorescein Derivatives for the Efficient High-Throughput Screening of
Lipases and Esterases in Aqueous Media. Helv. Chim. Acta 2006,
89, 404–415.
319
dx.doi.org/10.1021/co200006z |ACS Comb. Sci. 2011, 13, 310–320