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生命化学研究レター No.28 (2008 October)

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Enz NH2 (a)

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(7)

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CHNHQKATCRRMRSRETSVKK (rpf1368) Sequences of peptides

CXXXXXXXC XXXXXXX XXXXXXXXXXXX

Selection

Selection Libraries (first generation)

Libraries (third generation)

Sequences of peptides that bound to the diketone

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Selection Libraries (second generation)

Sequences of peptides that bound to the diketone NPLGAKLAGVFWWGQTPGG

R

O O

21-mer peptide Lys

NH

protein of interest

R O

R = Labeling compounds 21-mer peptide

Lys

protein of interest NH2

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HN O H

O

HN O

O OH

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weakly fluorescent highly fluorescent

H CO2Et O

R NHPMP H CO2Et

N H

O

R

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H CO2H

Me

anti-selective +

NH

syn-selective CO2H H CO2Et

O

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3 2 3 2

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R NHPMP H CO2Et

N R1

O

R2 PMP

anti-selective +

NH

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O

R NHPMP

NH CO2H

3 2 3 2

(2S,3S) Ketones (2S,3R)

Aldehydes

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1) Tanaka, F.; Fuller, R.; Shim, H.; Lerner, R. A.; Barbas, C. F., III. J. Mol. Biol. 2004, 335, 1007-1018.

2) Tanaka, F.; Fuller, R.; Barbas, C. F., III. Biochemistry 2005, 44, 7583-7592.

3) Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 3510-3511.

4) Tanaka, F.; Fuller, R.; Asawapornmongkol, L.; Warsinke, A.; Gobuty, S.; Barbas, C. F., III. Bioconjugate Chem. 2007, 18, 1318-1324.

5) Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III. J. Am. Chem. Soc. 2003, 125, 8523-8528.

6) Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 325-328.

7) (a) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III.

Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett.

2004, 6, 2527-2530.

8) Tanaka, F.; Mase, N.; Barbas, C. F., III. J. Am. Chem. Soc. 2004, 126, 3692-3693.

9) (a) Mitsumori, S.; Zhang, H.; Cheong, P. H.-C.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 1040-1041. (b) Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 9630-9631. (c) Zhang, H.; Mitsumori, S.; Utsumi, N.; Imai, M.; Garcia-Delgado, N.; Mifsud, M.; Albertshofer, K.; Cheong, P. H.-Y.; Houk, K. N.;

Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2008, 130, 875-886.

10) Tanaka, F. The Chemical Record 2005, 5, 276-285.

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Enhancing Activity and Controlling Stereoselectivity in a Designed PLP-Dependent Aldolase M. D. Toscano, M. M. Müller, and D. Hilvert, Angew. Chem.

Int. Ed., 46, 4468-4470 (2007).

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J. Am. Chem. Soc., 130, 7798-7799 (2008).

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Kemp Elimination Catalysts by Computational Enzyme Design

D. Röthlisberger, O. Khersonsky, A. M. Wollacott, L. Jiang, J. DeChancie, J. Betker, J. L. Gallaher, E. A.

Althoff, A. Zanghellini, O. Dym, S. Albeck, K. N. Houk, D. S. Tawfik and D. Baker, Nature, 453, 190-195 (2008).

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Differential High-Affinity Interaction of Dectin-1 with Natural or Synthetic Glucans is Dependent upon Primary Structure and is Influenced by Polymer Chain Length and Side-Chain Branching E. L. Adams, P. J. Rice, B. Graves, H. E. Ensley, H. Yu, G. D. Brown, S. Gordon, M. A. Monteiro, E.

Papp-Szabo, D. W. Lowman, T. D. Power, M. F. Wempe, and D. L. Williams, J. Pharmacol. Exp. Ther., 325, 115-123 (2008).

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Barrat, J. Exp. Med., 203, 1999-2008 (2006).

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Lamphier, W. P. Duprex, T. Espevik, and D. T. Golenbock, Nat. Immunol., 8, 772-779 (2007).

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