HOME＞ケージド化合物のデータリスト＞Bhcmoc-DiC8

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Bhcmoc-diC8

3-[(6-Bromo-7-hydroxycoumarin-4-yl)-methoxycarbonyl]- 1,2-dioctanoyl-glycerol ( Bhcmoc-diC8)

Structure		Absorption Spectrum
Photochemical and Photophysical Properties
substrate	λ^a(ε)^b	φ_dis^c	φ_app^d	φε^e	s^f	t_1/2^g
Bhcmoc-diC8	343 (11,600)	0.014	nd	160	nd	37
[a] Absorption maximum (nm) measured in K-MOPS (pH 7.2). [b] Molar absorptivity (M-1cm-1). [c] Quantum yields for the disappearance of the starting materials upon irradiation (350 nm). Samples (10 uM) in K-MOPS (pH 7.2) were photolysed with two RPR 350 nm lamps. [d] Quantum yields for the appearance of the product upon irradiation (350 nm). [e] The product of quantum yields for the disappearance and molar absorptivity at 350 nm. [f] Solubility (uM) in K-MOPS (pH 7.2) containing 1% DMSO. [g] Half-life (h) in the dark. Samples (10 uM) in K-MOPS (pH 7.2) were placed in the dark at room temperature.

Spectroscopic Properties

1H NMR (270 MHz, CDCl3) 7.63 (s, 1H), 7.05 (s, 1H), 6.40 (t, 1H, J = 1.3 Hz), 5.33 (m, 1H), 5.28 (d, 2H, J = 1.3 Hz), 4.45 (dd, 1H, J = 11.9, 4.0 Hz), 4.35 (dd, 1H, J = 11.5, 4.3 Hz), 4.31 (dd, 1H, J = 11.5, 5.3 Hz), 4.20 (dd, 1H, J = 11.9, 5.6 Hz), 2.35 (t, 2H, J = 7.6 Hz), 2.34 (t, 2H, J = 7.6 Hz), 1.62 (m, 4H), 1.28 (m, 16H), 0.87 (m, 6H)
13C NMR (67.5 MHz, CDCl3) 173.4 (s), 173.0 (s), 160.2 (s), 155.9 (s), 154.4 (s), 154.2 (s), 147.4 (s), 126.8 (d), 111.6 (s), 111.3 (d), 106.9 (s), 104.4 (d), 68.5 (s), 66.6 (t), 64.4 (t), 61.7 (t), 34.1 (t), 34.0 (t), 31.6 (t), 29.0 (t), 28.9 (t), 24.8 (t), 22.6 (t), 14.0 (q)
IR (ATR) 3375 (broad), 1724, 1607, 1441, 1409, 1280, 1218, 1160 cm-1
MS (ESI) m/z 663.00 (C₃₀H₄₁⁷⁹BrO₁₀+Na⁺), 664.80 (C₃₀H₄₁⁸¹BrO₁₀+Na⁺)

References

synthesis
1) A. Z. Suzuki, T. Watanabe, M. Kawamoto, K. Nishiyama, H. Yamashita, M. Iwamura and T. Furuta, Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols, Org. Lett., 5, 4867-4870 (2003). [PubMed] 　 →　method

application
1) V. G. Robu, E. S. Pfeiffer, S. L. Robia, R. C. Balijepalli, Y. Pi, T. J. Kamp, J. W. Walker, J. Biol. Chem., 278, 48154-48161 (2003).