HOME＞ケージド化合物のデータリスト＞Bhc-cGMP/Ac

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Bhc-cGMP/Ac

7-Acetoxy-6-bromocoumarin-4-ylmethyl guanosine cyclic 3',5'-monophosphate, Bhc-cGMP/Ac

Structure		Absorption Spectrum
Photochemical and Photophysical Properties
	λ^a(ε)^b	φ_dis^c	φ_app^d	φε^e	s^f	t_1/2^g
Bhc-cGMP/Ac	320 (5120)	0.161	0.146	175	nd	17
[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 cyclic nucleotides 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) for the deacetyl reaction.

Spectroscopic Properties

1H NMR (CD3OD) (axial isomer): d 8.04 (1H, s), 7.82 (1H, s), 7.36 (1H, s), 6.63 (1H, s), 5.92 (1H, s), 5.55-5.45 (3H, m), 4.64-4.50 (4H, m), 2.37 (3H, s). (equatorial isomer): d 8.05 (1H, s), 7.83 (1H, s), 7.35 (1H, s), 6.69 (1H, s), 5.95 (1H, s), 5.48 (2H, d, J=7.3 Hz), 4.64-4.50 (5H, m), 2.36 (3H, s); HRMS (FAB+) Calcd for C22H20O11N5BrP: 640.0081 and 642.0061. Found: 640.0101 and 642.0104.

References

synthesis
1) T. Furuta, H. Takeuchi, M. Isozaki, Y. Takahashi, M. Sugimoto, M. Kanehara, T. Watanabe, K. Noguchi, T. M. Dore, T. Kurahashi, M. Iwamura, R. Y. Tsien, Bhc-cNMPs as either water-soluble or membrane-permeant photo-releasable cyclic nucleotides for both one and two-photon excitation, ChemBioChem, 5, 1119-1128 (2004).

application
1) T. Nishigaki, C. D. Wood, Y. Tatsu, N. Yumoto, T. Furuta, D. Ellias, K. Shiba, S. A. Baba, A. Darszon, A sea urchin jelly peptide induces a cGMP-mediated decrease in sperm intracellular Ca2+ before its increase, Dev. Biol. 272, 376-388 (2004).