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No.28 (2008 October)
1
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FY¢78!•ž‚C!JN
（http://www.chem.eng.osaka-u.ac.jp/FBC/）
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The power of the dream
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No.28 (2008 October)
î î î
2
The power of the dream
î
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őĔùĄěî ĒăęĦî [email protected]Œ
No.28 (2008 October)
3
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No.28 (2008 October)
6
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high substrate specificity
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O
N
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O
O
O
N
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No.28 (2008 October)
7
EMFT‚7†(g¶!8QDUQl€0RCS8QDUQl€7·u4KIAD*;P>LU
&$‘±²¡»)@<&$fž4(*Wn%"!OJQevyc(fž4!/(*N
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%*'Àz&*Ÿ'4l€7£›2{°)·u%4&¸4
Libraries (first generation)
CXXXXXXXC
XXXXXXX
XXXXXXXXXXXX
Selection
Sequences of peptides
CHNHQKATC
AAVAKPP
VSVQTKY
NPLGAKL
AAMDAKNSPASA
DLPIPTTKLGRS
Libraries (third generation)
CHNHQKATCTAQAQSXXXXXX
CHNHQKATCRRMRSRXXXXXX
CHNHQKATCSWVLVPXXXXXX
CHNHQKATCPRDRHGXXXXXX
NPLGAKLAGVFWWXXXXXX
NPLGAKLAMAMWGXXXXXX
Libraries (second generation)
CHNHQKATCXXXXXX
AAVAKPPXXXXXX
XXXXXXAAVAKPP
VSVQTKYXXXXXX
XXXXXXVSVQTKY
NPLGAKLXXXXXX
XXXXXXNPLGAKL
AAMDAKNSPASAXXXXXX
XXXXXXAAMDAKNSPASA
DLPIPTTKLGRSXXXXXX
XXXXXXDLPIPTTKLGRS
Selection
Sequences of peptides that bound to the diketone
CHNHQKATCRRMRSRETSVKK (rpf1368)
Selection
NPLGAKLAGVFWWGQTPGG
Sequences of peptides that bound to the diketone
CHNHQKATCTAQAQS
CHNHQKATCRRMRSR
CHNHQKATCSWVLVP
CHNHQKATCPRDRHG
NPLGAKLAGVFWW
NPLGAKLAMAMWG
qÍÊ?=CT&:EMFT7‚4KIAD74)(_ž!KIADO9HOPU
21-mer peptide protein of interest
21-mer peptide protein of interest
Lys
Lys NH2
O
NH O
O
R
R
R = Labeling compounds
qÎÊ:EMFT7‚4KIAD7@<&$ž²¡»(OJQ7yc4‰•
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ÀzpÆ%4¥^¢(Ç,Y¯ˆ8QBGD):EMT7«48QDUQl€L9=Ql€
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No.28 (2008 October)
8
ƒŽKWcs^-p*›a/;AE†t–&Yq{I-¡¢žM*
')V„‰
‹/=B1F‰Š‰*›aYq-§ˆ*tT
H
N
N
O
+
N
O
N
O
N
O
O
H
N
O
highly fluorescent
weakly fluorescent
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:FB›a-.B:FBYq]žM*'w€Hn›a§ˆ&r
žMmŽ•(+*
O
O
+
O
H
OH
H
N
H
N
O
O
weakly fluorescent
highly fluorescent
\­«˜O_U').B:FBYq£™-}Q*w€YqL
`—&†…rƒ JRbyWZƒ*JRbyWZƒ-‘XdPV„‰
¨¤u‰Zt*w€§ˆz"+*¥’/;AE~'*›a–”JRbyWZƒ
)(z#†tƒ-¤u‰G*Yq-›a*Rb-œSšOcr.A>¦Ÿ
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Zƒ~hG*yZ
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V 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.
No.28 (2008 October)
10
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h †vˆ…IM…<V’ˆ‚Š}‹…zqi7
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F2x{ˆzj|nzv‚ikQW.g`N„Œ•–”Z)#l’‹nA[‰]“;yŠ~‘n‚
1€mˆzj|…A„ƒppŽˆ{“qi6^i „Œ•–”Zš™›…}Š…&"˜œŸ—
…3„ŽO‰!Šˆy}j@i7
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1. Tahara, Y. et al., J. Control. Release, doi:10.1016/j.jconrel.2008.07.015 (2008).
2. Yokoyama, K., Nio, N., Kikuchi, Y. Appl. Microbiol. Biotechnol., 64, 447–454 (2004).
3. Kamiya, N., Tanaka, T., Suzuki, T., Takazawa, T., Takeda, S., Watanabe, K., Nagamune, T. Bioconjugate Chem., 14,
351-357 (2003).
4. Takazawa, T., Kamiya, N., Ueda, H., Nagamune T. Biotechnol. Bioeng., 86, 399-404 (2004).
5. Tanaka, T., Kamiya N., Nagamune T. FEBS Lett., 579, 2092-2096 (2005).
No.28 (2008 October)
17
6. Mao, H., Hart, S. A., Schink, A., Pollok, B. A. J. Am. Chem. Soc., 126, 2670-2671 (2004).
7. Hirakawa, H., Kamiya N., Tanaka, T., Nagamune T. Protein Eng. Des. Sel., 20, 453-459 (2007).
8. 53 p.21-26 (2005).
9. Kamiya, N., Doi, S., Tominaga, J., Ichinose, H., Goto, M. Biomacromolecules, 6, 35-38 (2005).
10. Y. Tanaka, Y. Tsuruda, M. Nishi, N. Kamiya, M. Goto. Org. Biomol. Chem., 5, 1764-1770 (2007).
11. Fontana, A., Spolaore, B., Mero, A., Veronese, F. M. Adv. Drug. Deliv. Rev., 60, 13-28 (2008).
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Ed., 46, 8819-8822 (2007).
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14. Hu, B.-H., Messersmith, P. B. J. Am. Chem. Soc., 125, 14298-14299 (2003).
15. Gronemeyer, T., Godin, G., Johnsson, K. Curr. Opin. Biotechnol., 16, 453-458 (2005); O'Hare, H. M., Johnsson, K.,
Gautier, A. Curr. Opin. Struct. Biol., 17, 488-494 (2007).
16. Lin, C.-W., Ting, A. Y., J. Am. Chem. Soc., 128, 4542-4543 (2006).
No.28 (2008 October)
18
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-EÙåÁØEì¥&ÖÊÔnÌèزëæͼ,dØÚ×À$¤frAäOÊÀ\ìãѼU
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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).
º Hilvert æ Ú Geobacillus stearothermophilus o W Ù
PLP-dependent alanine racemase ٛ-^$Õ¿è 265 qt
Ù Tyr ^ $ ì Ala ^ $ Ø  J Ì è È Ö Ù à Ø å Ò Ô ¼
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ĀÖôĊöĎÞÙ§ïċĀďċ@Ú 105 ¨ÉéèÈÖÄ
ÙaA­Ĉÿċ a) ¯m" b) Tyr265Ala )
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rÖ(2R,3S)--phenylserine-PLP aldimine ˜
ì Ala ^$Ùà×æͼSer, Val, Glu, Arg, Lys ^$؍J
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PLP aldimine ˜ d) Met134Phe/Tyr265Lysº
Tyr265Lys )rÚ Tyr265Ala Ø3Ê 9 Ù kcat ìyÊßÊ
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R>ؼ(2R,3S)-, (2R,3R)-ăðāċúĊĎìnÀ÷ïøþČñ«GAÙYì–ÒÔÀß̽Tyr265Ala
No.28 (2008 October)
19
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µ®œŒ>r9ª’°š¶¦˜¶«‹H2{ªE©!
Q¸(œ´ —¥‹racemase “² aldolase ­¦Da¸8!œ
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The Putative Diels-Alderase Macrophomate Synthase is an Efficient Aldolase
J. M. Serafimov, D. Gillingham, S. Kuster, and D. Hilvert
J. Am. Chem. Soc., 130, 7798-7799 (2008).
Š ËÙÂŪRf Macrophoma commelinae P?ª
Macrophomate synthase (MPS) « 3 ©Vœ 2-ÔÞß(1)“²
×ÂÞÕ¾Øß(2)­ªjƒ¨!71¸m$œ´˜¦”·
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Biomimetic Catalysis of intermodular Aminoacyl Transfer
K. M. Wilcoxen, L. J. Leman, D. A. Weinberger, Z.-Z. Huang, and M. R. Ghadiri, J. Am. Chem. Soc., 129,
748-749 (2007).
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21
Eé ¸¨B Łïîé ēđøł
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ŀīĉËÊüĂNß®ČĆîĈčÏtĝŃ:ù¯úĀĈîĂăôĒþë
Design of Protein Function Leaps by Directed Domain Interface Evolution
J. Huang, A. Koide, K. Makabe, and S. Koide, Proc. Natl. Acad. Sci. USA, 105, 6578-6583 (2008).
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22
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F. Fan, B. F. Binkowski, B. L. Butler, P. F. Stecha, M. K. Lewis, and K. V. Wood, ACS Chem. Biol., 3,
346-351 (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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24
M :Ėèàï ÓìÐÌė
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Ü3âˆÝÄð-1,3-ûĐøēóc³œâùčďõĕá{ÅðÎÞóSÒ؃‹áJÒÜÈïç
ÔÂõēăāēÿc³ë siRNA Êc³œÞÒ܃‹ÐñÜÅçÔÊÁ~pK{ó„Ô CpG DNA Þ
(äñð 1 ^µâ÷ďý DNA áoÒÜÁ -1,3-ûĐøēó DDS _ZÞÒÜ{ÅÁ i€ÝÄðP!U„
’˜áÎâc³œóa€á­°ÔðOŸó–èÒØÅޗÇÜÅçÔ Îâ CpG DNA ÞÅÆ%ã
»ċăĐ CG þĆúđ÷ăąâ²Êšeuâ~ópKÔðÎÞá|`ÒÜÅçÔ ^‰ÝãÁ
ùčďõĕÞÒÜ{Ôð-1,3-ûĐøēâ"9(Dectin-1)á·ÒÜ/ÞÁ c³œÞÒÜâ CpG DNA
á·ÒÜ/Á Ðîá CpG DNA â"9(TLR9)á·ÒÜ/óÖñ×ñϓÐÕܾËçÔÂ
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).
2001 Câ nature ¤Ý Gordon zîãĊöÿĔĊúĒĈôĕþh’˜b(RAW264.7)á-1,3-ûĐøēâ
đāĉĂĕÞÒÜ Dectin-1 ÊxÒÜÅðÞ/&ÒçÒØÂÎ⃋ʍÞàÚÜÁ¥«±ë¹K’˜
âv7ÁçØĂēćúâ}KâT‘Á~pKáÈÍð Dectin-1 âGŽáÛÅÜpàƒ‹ÊQÒ
¯éîñÜÅçÔÂ^ªYÝãÁ-1,3-ûĐøē⵶ëµÊ Dectin-1 å⥫áßâíÆàF½ó
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À 7 l-Éîàð‚µwâûĐøēó{LÒÁÇÜ 8Á9Á
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Dectin-1(ĊöÿĔ”VÇ,)åâ•$™ã ¼ĉĎĀČē
nÝ©æîñÁµsD IC50 ÞÒÜm¬ÐñÜÅçÔ‚
µwâûĐøēâ IC50 ã 7 l-â >1 mM Éî 10 l-â
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çØ 9 l-Ýã 2.6 mM Éî 29 μM åÞ 0.01 ‡DáçÝr=ÒÜÈïÁ1 ÛâûĐüĕÿµâ
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Dectin-1 å⥫™óféÜ4ËÌ¿éðÎÞó„ÒÜÅçÔ ) 1 ãÁ‚µûĐøē(10 l-)Þ>ûĐ
øē(9 l-+µ 1 l-)â5ČĄĐó¡ÒØêâÝÔÂÎÎÝÁ6 l-âûĐüĕÿÊ 1 Ăĕēâ[
óEMÔðÎÞó„ÒØIáÁµÊÄðÎÞÝČЊÊr=ÒÜÈïÁÖâ•azÓ؝[g®âAÊ
Dectin-1 å⥫áF½óÇðÞHîãUdÒÜÅçÔ NÃâûĐĕĉÝãÁ56nó{Å
No.28 (2008 October)
25
áāęĂĞƸç2*Ð-1,3-āęÿĝç 3 µžXç¸çŒ³?æÍóBÀ÷ªêȸÐ
ÙóãžX&(çmçy.Ð/öòȞXçĒċĊЈÒåóÕã÷‰×áËëÙɑ猳?㟧
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Properties Regulating the Nature of the Plasmacytoid Dendritic Cell Response to Toll-Like Receptor 9
Activation
C. Guiducci, G. Ott, J. H. Chan, E. Damon, C. Calacsan, T. Matray, K. D. Lee, R. L. Coffman, and F. J.
Barrat, J. Exp. Med., 203, 1999-2008 (2006).
CpG DNA 烢è 1984 =ç BCG ç DNA ~æ@
åúĝĉĞēüěĝ¨7—ÐÊóãËÌHn Izñ
ç,%æ²òëÙÉÛçEÈ1992 =æ DNA ç CG ąĐ
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1995 =æèÈKrieg zñÐ0™}^ç DNA æ B ’
–çrL—ÐÊòÈÖñæ CG ç¿ĖĊęÐrLæJ
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No.28 (2008 October)
26
Ligand-Induced Conformational Changes Allosterically Activate Toll- Like Receptor 9
E. Latz, A. Verma, A. Visintin, M. Gong, C. M. Sirois, D. C. G. Klein, B. G. Monks, C. J. McKnight, M. S.
Lamphier, W. P. Duprex, T. Espevik, and D. T. Golenbock, Nat. Immunol., 8, 772-779 (2007).
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