201912v51
Newsletter
NMDA 38
Ru Fc 40
59
2
1970 80
3
4
2014 72016 10 JST
2 PPI
PPI Fig. 1a 1[5-8]
Newsletter-- Vol.34, No.2 (2019. 12)
5
[9] 2. COI1-JAZ in vitro in silico JA-Ile COI1-JAZ
COR, 3
COR JAZ
[10,11]COR
CFA, 4
CMA, 5
4 3, ent3, 6, ent6, Fig. 2 COI1-JAZ9
Y2H4
[11] ent6 Y2H COI1-JAZ9
JAZ COI1-JAZ
Y2H Y2H
COI1-JAZ
JAZ
JAZ
Figure 1. (a-c) a: [2]b:
[3]c: [5]. (d) 1 JA-Ile2
COI1-JAZ .
6
COI1-COR- JAZ1 X [5]COI1
JAZ1 COI1-COR Jas motif
JAZ Jas motif
anti-Fluorescein JAZ
JAZ1 GST COI1 COR3 COR
ent3anti-Fluorescein anti-GST
Fig. 2aCOI1-JAZ1 COR JA-Ile PPI ent3 JA
COI1-JAZ PPI Fig. 2b 4 COR Jas motif
JAZ COI1 PPI COR COI1-JAZ
ent6 COI1-JAZ3, 9-12 5 PPI ent6 in vitro
JAZ
COR-JAZ1 JAZ in silico docking study
COR
ent6 COI1-JAZ3, 9-12 COR
Figure 2. (a) OG JAZ pull-down . (b)
. (c) COR . (d) COR COI1-JAZs
(I.S. = ).
7
NOMeNOPh NOBn
JAZ
NOPh8 JAZ9 10
13 JAZ 2
Fig. 3b 3. COI1-JAZ in vivo 8
1 COR
ent6 8
8
PDF1.2 COR 5
ORA59
50 µM 5 A. brassicola COR
Fig. 4[9] in vitro JAZ9/10
in vivo
JAZ
ORA59 jaz10-1 mutant
jaz9-1 mutant
Figure 3. (a) ent6. (b) ent6, 79 COI1/JAZ .
Figure 4. COR (3) NOPh (8)
(a) (b).
8
[13] 8 COI1/JAZ9
ERF1-EIN3/EIL1-ORA59 MYC
COR JA-Ile
in vitro JAZ
JAZ 4.
2016 Greg Howe 13 JAZ 5 5
6
[14] 10 11 JAZ jazD, jazU[15] JAZ
[17] ITbM
Bump-and-hole [18]
2018 in silico
Roberto Solano Andrea Chini
JST JSPS
[1] Jiang, K.; Asami, T. Biosci. Biotechnol. Biochem., 2018, 82,
1265. [2] Murase, K.; Hirano, Y.; Sun, T.-P.; Hakoshima,
T., Nature 2018, 456, 459 (PDB ID: 2ZSH). [3] Tan, X. et al. Nature
2007, 446, 640 (PDB ID: 2PIQ). [4] Santiago, J. et
al. Nature 2009, 462, 665. [5] Sheard, L. B. et al. Nature 2010,
468, 400 (PDB ID: 3OGM). [6] Thins, B. et al. Nature 2007,
448, 661. [7] Chini, A. et al. Nature 2007, 448, 666. [8] Fonseca,
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et al. Proc. Natl. Acad. Sci. USA 2018, 115, E10768.
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N. et al. Nat. Chem. Biol. 2018, 14, 299.
Newsletter-- Vol.34, No.2 (2019. 12)
9
2011–2012
2012–2019
2016–2018 Nathan W. Luedtke
2019 7
BrdU DNA
Fig. 11BrdU 5
10
5-ethynyldeoxyuridineEdU
DNA 2EdU Huisgen Copper catalyzed Azide-Alkyne
CycloadditionCuAACDNA
CuAAC
3 DNA
4CuAAC
DNA 5-azidomethyldeoxyuridineAmdU
dimorpholino- cycloocadiyneDiMOC DNA
2. POM-AmdUChemBioChem, 2018, 19, 1939. Luedtke 5
AmdU 5AmdU Strain-Promoted Azide-Alkyne CycloadditionSPAAC 6
AmdU
NH2 O
PO OPh
NH O
OAB I2, pyridine
OAB O
11
HINT-1 ProtideProt10
Scheme 1AmdU DNA
3
HeLa 24 DNA
CuAAC DNA Fig. 2
POM-AmdU AB-AmdU DNA AmdUProt- AmdU HeLa AmdU
HINT-1 AB-AmdU HeLa
U2OS 12
AB-AmdU POM-AmdU AB-AmdU 2
AB-AmdU
11POM-AmdU DNA
POM-AmdU U2OS AML
POM-AmdU
Fig. 2 AmdU POM-, AB-, Prot-AmdU 10 µM HeLa
24 . 2M HCl DNA AlexaFluoro-594-
Huisgen DNA . POM-AmdU
DAPI.
12
DNA
2 122010 CODY
SPAAC 13
Scheme 2 8
14 DiMOC
DiMOC X
CODY
DiMOC
> 10 mM DiMOC DNA DiMOC DNA
DNA DiMOC UV
DiMOC DNA 3 1
15 µM DiMOC AmdU
1.0 M-1•sec-1 DNA
DiMOC DNA
BCN-TAMRA 50 4%
AmdU BCN
Scheme 2. Dimorpholino cyclooctadiyne (DiMOC) . NBS =
N-bromosuccinimide, AIBN = azobis(isobutyronitrile), DIBAL-H =
diisobutylaluminium hydride, LHMDS = lithium
bis(trimethylsilyl)amide, LDA = lithium diisopropylamide.
CO2H
Me
LHMDS, ClP(O)(OEt)2 -78ºC
ON NO
13
ODN-1 DiMOC N3- TAMRA ODN-1 5
DNA
DAPI DiMOC
AmdU
2'(R)-azidodeoxyadenosineDNA
Fig. 4 RNA 2'(R)-azidodeoxy adenosineDNA AzC
.
Fig. 3 a) DiMOC AmdU DNA SPAAC . b) BCN-TAMRA N3-TAMRA
. c) AmdU DNAODN-1 BCN-TAMRA DiMOC/N3-TAMRA
. ODN-1 T AmdU . d) POM- AmdU HeLa BCN-TAMRA DiMOC/N3- TAMRA DNA
.
Newsletter-- Vol.34, No.2 (2019. 12)
14
DiMOC N3-TAMRA RNADNA
AzC DiMOC/N3-TAMRA DNA AzC
15
3-2. DiMOC DNA Angew. Chem. Int. Ed., 2018, 57, 15405. Cis-Pt
DNA-DNA ICL
POM-AmdU DNA 2
DiMOC DNA-DNA
AmdU DiMOC ICL
Fig. 5 ODN-2 AmdU ODN-3
AmdU Fig. 5a
ODN DiMOC 2 ODN-2
Fig 5b, lane 2 MALDI-MS ICL Fig. 5c 2.1 x 105 M-1•sec-1
AmdU DiMOC 10 DiMOC
DNA HeLa POM-AmdU 72
2 PD time = 30 DiMOC
ICL
denaturing-renaturing ICL POM-AmdUDiMOC
Fig. 5 a) DiMOC AmdU DNA ICL . b) ODN-2ODN-3 DIMOC
. c) Lane 2 MALDI-MS .
Newsletter-- Vol.34, No.2 (2019. 12)
15
DNA 100-300 bp DNA
ICL
Fig. 6aICL
POM-AmdU DiMOC DNA S1
Fig. 6b, lane 8, 10, 12
UPLC-MS ICL
Fig. 6c, dAmdU-DiMOC ICL
DiMOC POM- AmdU DiMOC
DiMOC SPAAC
DiMOC
Fig. 6 a) DNA ICL denaturing-renaturing . b) DNA
denaturing-renaturing S1 . c) S1
UHPLC-MS m/z=513.20–513.21 SIM . d) ICL .
Newsletter-- Vol.34, No.2 (2019. 12)
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POM-AmdU DiMOC DNA
POM-AmdU HeLa IC50 > 100 µMDiMOC DNA BrdU EdU
DiMOC
Department of Chemistry, University of Zurich Nathan W. Luedtke
McGill UniversityLuedtke DiMOC X
Tony Linden University of ZurichUPLC-MS Jorn Piel
ETH Zurich
Dr. Helmut Legerlotz Foundation [1] R. C. Leif, J. H. Stein, R. M.
Zucker, Cytometry 2004, 58A, 45–52. [2] A. Salic, T. J. Mitchison,
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Newsletter-- Vol.34, No.2 (2019. 12)
17
DNA RNA
GNA[4]
XNA
D-aTNA (acyclic D- Threoninol Nucleic Acid)[5], L-aTNA (acyclic
L-
Figure 1.
18
Threoninol Nucleic Acid)[6], SNA (Serinol Nucleic Acid)[7] 3
(Fig. 1) D-aTNA DNA RNASNA
L-aTNA
[8]
XNA XNA
XNA
DNA (Fig. 3)[10]
DNA L-aTNA N-Cyanoimidazole
2. L-aTNA 16-mer L-aTNA (Template) 8-mer L-aTNA (8A8B)8B
3’8A 1’8A 3’
PAGE (Fig. 4)
Figure 2.
19
DNA ( 27%) L-aTNA (74%)
N-Cyanoimidazole
L-aTNA DNA
DNA
N-Cyanoimidazole
DNA 2
DNA 1
L-aTNA
2
Figure 4. L-aTNA () () Reaction conditions: 4oC, 12 h, [oligomer] =
1.0 μM, 20 mM N-Cyanoimidazole, 20 mM ZnCl2, 100 mM NaCl,
Denaturing PAGE: 15% AA, 8 M Urea, 1.5 h, 750 V.
Figure 5.
Reaction conditions: 25oC, [oligomer] = 1.0 μM, 10 mM N-
Cyanoimidazole, 20 mM MnCl2, 100 mM NaCl.
Newsletter-- Vol.34, No.2 (2019. 12)
20
L-aTNA
L-aTNA (Fig. 6)
PCR
L-aTNA
8- mer 5-mer, 4-mer, 3-mer, 2- mer
(Fig. 7)6h 5- mer 4-mer
24h 3-mer
DNA
Figure 7. L-aTNA
Reaction conditions: 4oC, [8A] = [Template] = 1.0 μM, [5B] = [4B] =
[3B] = [2B] = 10 μM, 10 mM N-Cyanoimidazole, 20 mM MnCl2, 100 mM
NaCl.
Figure 6. L-aTNA
Newsletter-- Vol.34, No.2 (2019. 12)
21
(Fig. 8) 12-mer
16-mer
12h 84% A
L- aTNA
L-aTNA DNA
L-aTNA SELEX XNA
XNA Prebiotic world ”XNA world”
Figure 8.
Reaction conditions: 4oC, [8A] = [Template] = 1.0 μM, [4B] = [4B’]
= 10 μM, 10 mM N-Cyanoimidazole, 20 mM MnCl2, 100 mM NaCl.
Newsletter-- Vol.34, No.2 (2019. 12)
22
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Newsletter-- Vol.34, No.2 (2019. 12)
23
PPI PPI
1990
NSA 1a[4]
φ, ψ, ωφψ 1,3-
bω
Newsletter-- Vol.34, No.2 (2019. 12)
24
N N
2006 Arvidsson [6] N
NSA
NSA MD
NSA 500
0.8
1.6
NSA
NSA DEER
NSA
NSA
NSA (a)
(b) NSA φψ(c) NSA
25
1HCOSYHMQCHMBC NMR
NOESY
4. NSA PPI NSA
NSA N
PPI MDM2 p53
MDM2 p53
p53 C transactivation domainTAD
p53-TAD Phe19Trp23Leu26 a[7]
NSA N p53-TAD
b1 N
NSA
c
NSA KD = 1.1 µM MDM2
NSA MDM2 p53-TAD
Ki = 0.93 µM MDM2 p53-TAD
NSA
MDM2 NSG
DEER NSA NSG
Tikhonov
26
NSG MDM2 NSA MDM2
PPI
PPI
PPI [8] Kodadek Lim
[9,10]
D2
MDM2-p53 NSA PPI (a) p53-TAD MDM2 (b)
p53-TAD NSA p53 F19W23
L26 αβ NSA Nα (c) p53
NSA MDM2-p53
27
CREST [1] Simon, R. J.; Kania, R. S.; Zuckermann, R. N.; Huebner,
V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.;
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2016, 55, 602–606.
Newsletter-- Vol.34, No.2 (2019. 12)
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P-
-
2
PPI
P-
S-S
20
29
2P-
()Y140 (
)()
X
X X
(Fig. 3) PPI
PPI
P-
JSPS [1] Kudo, S.; Caaveiro, M. M. J.; Tsumoto, K. Structure, 2016,
24, 1523. [2] Senoo, A.; Nagatoishi, S.; Moberg, A.; Babol, N. L.;
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Miyafusa, T.; Matsuura T.; Sudou Y.; Tsumoto K. Sci. Rep., 2017, 7,
39518
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30
“
31
SELEX FGFR2
DNA
FGFR2 A
FGFR2
FGFR2 2.
[1] Sarabipour and Hristoba. Nat. Commun. 2016, 4:7, 10262. [2]
Ueki et al., Angew. Chem. Int. Ed., 2016, 55, 579. [3] Ueki et al.,
J. Am. Chem. Soc. 2017, 139, 6554.
. Aptamer
32
photoSLIPT
1 2JST
1990
1.
CFPGFPYFP mCherry
SLIPT
a
b
33
eDHFR TMP
o-(NVOC)
NVOC CFPGFP
(PIP3)PIP3
PIP3
PI3K mDcTMPNVOC
( 2a)PI3K p110 iSH2 eDHFR
(eDHFR-Venus-iSH2)eDHFR-Venus-iSH2 iSH2
eDHFR-Venus-iSH2 mDcTMPNVOC
3
( 2b)photoSLIPT
[1] Ishida, M.; Watanabe, H.; Takigawa, K.; Kurishita, Y.; Oki, C.;
Nakamura, A.; Hamachi, I.; Tsukiji, S. J. Am.
Chem. Soc. 2013, 135, 12684. [2] Nakamura, A.; Katahira, R.;
Sawada, S.; Shinoda, E.; Kuwata, K.; Yoshii, T.; Tsukiji, S.
Biochemistry. in press [3] Nakamura, A.; Oki, C.; Kato, K.;
Fujinuma, S.; Maryu, G.; Kuwata, K.; Yoshii, T.; Matsuda, M.; Aoki,
K.;
Tsukiji, S. ChemRxiv, DOI: 10.26434/chemrxiv.8222456
a
b
34
RNA
4
RNA G- quadruplex 1)G-quadruplex
G-quadruplex
RT 3)RNA
cDNA
G-quadruplex Fig. 2
RNA Staple DNA
Fig. 1. Staple mRNA RNA G-quadruplex
Newsletter-- Vol.34, No.2 (2019. 12)
35
RNA G-quadruplex
TPM3 5’UTR
Firefly luciferaseFluc mRNA
Staple
Staple G-quadruplex
TPM3 Staple
4. Staple mRNA G-quadruplex
Staple Staple
RNAi
[1] Kumari, S.; Bugaut, A.; Huppert, J. L.; Balasubramanian, S.
Nat. Chem. Biol. 2007, 3, 218–221 [2] Xu, S.; Li, Q.; Xiang, J.;
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Rep. 2016, 6, 24793. [3] Hagihara, M.; Yoneda, K.; Yabuuchi, H.;
Okuno, Y.; Nakatani, K. Bioorg. Med. Chem. Lett., 2010, 20,
2350-
2353.
Fig. 2. RT
36
1
1 1 2 3 1 4 4 5 6 7 3,
8 1, 9, 10
123456
789 10AMED-CREST
37
[2]
alkaline
phosphatases (ALPs)
ALPTNAP
Fig.3
ectonucleotide
pyrophosphatases/phosphodiesterases (ENPPs)
(Fig 5)
[1] R.Watanabe et al., Nat. Commun, 2014, 5, 4519. [2] S.Sakamoto
et al., Sci. Adv, in press
Fig 4. AENPP
B
A
B
38
NMDA
………
(NMDAR)AMPA (AMPAR)
AMPAR
NMDAR NMDAR
NMDAR
39
NMDA
[1] Fujishima, S. et al. J. Am. Chem. Soc., 2012, 134, 3961. [2]
Wakayama, S. et al. Nat. Commun., 2017, 8,14850
2(a)
(b) 2
LDAI (0h)
LDAI()
40
1 2
1,2, 1,2, 1, 1
2011 -2016
2016 -2018
2018 -2020
[1] ADC
Fc
1-methyl-4-aryl-urazole(MAUra) Ru
Fc
Figure 1.
41
ApA[4] Ru [5]
Fc (Figure 2a)Ru
HER2 CD20
EGFR Fc (Figure 2b)
LC-MS/MS Fc
Ru
[1] Beck, A.; Goetsch, L.; Dumontet, C.; Corvaïa, N. Nat. Publ. Gr.
2017, 16 (5), 315.
[2] Yamada, K.; Ito, Y. ChemBioChem 2019, 20, 2729.
[3] Sato, S.; Hatano, K.; Tsushima, M.; Nakamura, H. Chem. Commun.
2018, 54 (46), 5871.
[4] Li, R.; Dowd, V.; Stewart, D. J.; Burton, S. J.; Lowe, C. R.
Nat. Biotechnol. 1998, 16, 190.
[5] Tsushima, M.; Sato, S.; Niwa, T.; Taguchi, H.; Nakamura, H.
Chem. Commun. 2019, 55, 13275.
Figure 2. Fc
42
1,2,3
,4,5JST-PRESTO,6AMED-CREST
4, 1,2,6
1
g-GGT
43
2 X
X
X Y
Y
GGT
Y GGT
[1] Urano, Y. et al. Science Transl Med, 3, 110 (2011). [2] Ueo, H.
et al. Sci. Rep., 5, 12080 (2015). [3] Asanuma,
D. et al. Nat. Commun., 6, 6463 (2015). [4] Komatsu, T. et al. J.
Am. Chem. Soc., 135, 6002-6005 (2013).
Newsletter-- Vol.34, No.2 (2019. 12)
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(Q)
45
D-aTNA
aTNA
Dabcyl
Q1
Q3 Cy3
FAM
9
(Fig.5)
[1] H. Asanuma, et al., J. Am. Chem. Soc., 2010, 132, 14702-14703.
[2] K. Murayama, et al., ChemBioChem, 2015, 16, 1298-1301.
Fig. 2. DNA D-aTNA
Fig. 3
46
WPI
47
Newsletter-- Vol.34, No.2 (2019. 12)
48
9 4 ()9 6 () 3 13
34 21
2007
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1340-1440
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COI 2011 2011 2006 2002
Newsletter-- Vol.34, No.2 (2019. 12)
54
−
20
230
2
MPC
55
56
34 22
3
12
345
5 4
1 2 31
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RSCRoyal Society
of Chemistry Organic & Biomolecular Chemistry Molecular
Omics
Newsletter-- Vol.34, No.2 (2019. 12)
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53
*1 *2 *3
*1 Molecular Omics *2 Organic & Biomolecular Chemistry *3
Metallomics
58
*1 Molecular Omics *2 Organic & Biomolecular Chemistry *3
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59
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14 35 23
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https://www.med.kyushu-u.ac.jp/100ko-do/ DDS HP . (1) (2) (3) (4)
(5) (6) (7) 15 5 . 2 HP .
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