2956
H. Nagano et al. / Tetrahedron Letters 44 (2003) 2953–2956
Figure 2. Photographs of plant sections in the binding experiments which shows specific binding of probe 1 with the motor cell
of Albizzia plants (upper: Nomarskii image of plant section, lower: fluorescent image of plant section after treatment with 1×10−4
M of probe 1 [excitation: 450–490 nm]).
Acknowledgements
8. Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org.
Chem. 1998, 63, 4248–4255.
This work was supported by the Ministry of Education,
Science, Sports and Culture (Japan) for Grant-in-Aid
for Scientific Research (No. 1302467 and 12680598),
Pioneering Research Project in Biotechnology given by
the Ministry of Agriculture, Forestry and Fisheries,
Kato Memorial Bioscience Foundation, Naito Founda-
tion, Kurata Foundation, Moritani Foundation. This
work was also supported by Grant-in-Aid for the 21st
Century COE program ‘KEIO Life Conjugate Chem-
istry’ from the Ministry of Education, Culture, Sports,
Science, and Technology, Japan.
9. 1: 1H NMR (270 MHz, CD2OD, 18°C): 8.03 (1H, d,
J=2.0 Hz), 7.66 (1H, brs), 7.38 (2H, d, J=8.6 Hz),
7.20 (1H, d, J=8.4 Hz), 7.13 (2H, d, J=8.6 Hz), 6.70–
6.58 (7H, m), 5.89 (1H, d, J=12.7), 4.30 (1H, m),
3.94–3.37 (8H, m), 3.01 (2H, t, J=7.0 Hz), 1.86–1.41
(4H, m); 13C NMR (100 MHz, DMSO, 18°C): 180.2,
171.8, 169.6, 166.1, 165.5, 159.1, 158.2, 156.9, 155.2,
140.2, 137.7, 132.3, 130.0, 129.3, 127.8, 126.1, 125.2,
120.8, 120.2, 118.4, 115.8, 114.8, 111.0, 102.6, 69.0,
68.2, 52.3, 45.7, 43.9, 29.1, 25.0, 11.5; HR FAB MS
(positive): [M+H]+ found m/z 796.2778, C40H42O9N7S
requires m/z 796.2765; IR (film) w: 3273, 1589, 1466,
;
1387, 1265, 1209, 1111 cm−1 [h]D20 +40.2° (c 1.0,
DMSO).
References
10. 2: 1H NMR (400 MHz, CD3OD, 25°C): 7.49 (1H, d,
J=9 Hz), 7.42 (2H, d, J=9 Hz), 6.69 (2H, d, J=9
Hz), 6.67 (1H, dd, J=2, 8 Hz), 6.64 (1H, d, J=12 Hz),
6.51 (1H, d, J=2 Hz), 5.86 (1H, d, J=13 Hz), 4.42
(1H, dd, J=6, 7 Hz), 3.54 (2H, s), 3.51 (5H, m), 3.37
(3H, m), 3.16 (2H, t, J=7 Hz), 2.35 (3H, s), 1.98 (6H,
s), 1.82 (1H, m), 1.72–1.51 (3H, m); 13C NMR (100
MHz, CD3OD, 18°C): 175.2, 173.9, 173.3, 170.0, 164.9,
159.4, 158.6, 155.9, 153.6, 153.0, 139.5, 132.6, 127.9,
127.5, 120.7, 116.0, 114.6, 113.5, 112.0, 100.7, 70.3,
70.2, 54.3, 42.0, 40.6, 40.5, 35.2, 30.2, 26.3, 20.7, 15.4;
HR FABMS (positive): [M+H]+ found 622.2983 m/z,
C31H40O7N7 requires 622.2989 m/z; IR (film) w: 3344,
1668, 1554, 1516, 1201, 1136, 721 cm−1; [h]D20 +14.1° (c
0.5, MeOH).
1. Lee, Y. In The Pulvinus in Motor Organ for Leaf
Movement; Satter, R. L.; Gorton, H. L.; Vogelmann,
T. C., Eds.; American Society of Plant Physiologists:
Rockville, 1990; p. 130.
2. Ueda, M.; Takada, N.; Yamamura, S. Bull. Chem. Soc.
Jpn. 2002, 75, 2337–2347.
3. Ueda, M.; Wada, Y.; Yamamura, S. Tetrahedron Lett.
2001, 42, 3869–3872.
4. Sugimoto, T.; Wada, Y.; Yamamura, S.; Ueda, M. Tet-
rahedron 2001, 57, 9817–9825.
5. Sugimoto, T.; Yamamura, S.; Ueda, M. Chem. Lett.
2002, 1118–1119.
6. Ueda, M.; Tashiro, C.; Yamamura, S. Tetrahedron
Lett. 1997, 38, 3253–3256.
11. Probe 2 gave dim image and clear image with high
resolution was not obtained.
7. Ueda, M.; Okazaki, M.; Ueda, K.; Yamamura, S. Tet-
rahedron 2000, 56, 8101–8105.