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A novel method for the synthesis of sulfur substitutedcyclopyrophosphate of cADPR analogs |
Ren-Min Wu, Na Qi, Yu-Wen Jia, Zhu Guan, Liang-Ren Zhang, Li-He Zhang, Zhen-Jun Yang |
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China |
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Abstract A facile and efficient protocol for the synthesis of sulfur substituted-cyclopyrophosphate of cIDPRE (PS1-cIDPRE) was developed. The key step was the cyclization process which was completed by the sulfur substituted cyclization precursor 1b via the one-pot phosphoramidite strategy.
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Received: 03 June 2014
Published: 23 July 2014
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Fund: Weare grateful for scientific research funding from the National Natural Science Foundation of China (Nos. 21332010, 21172010, 21002004). |
Corresponding Authors:
Zhen-Jun Yang
E-mail: yangzj@bjmu.edu.cn
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[1] |
H.C. Lee, Physiological functions of cyclic ADP-ribose and NAADP as calcium messengers, Annu. Rev. Pharmacol. Toxicol. 41 (2001) 317-345.
|
[2] |
A.H. Guse, Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR), Curr. Med. Chem. 11 (2004) 847-855.
|
[3] |
L. Xu, T.F. Walseth, J.T. Slama, Cyclic ADP-ribose analogues containing the methylenebisphosphonate linkage: effect of pyrophosphate modifications on Ca2+ release activity, J. Med. Chem. 48 (2005) 4177-4181.
|
[4] |
X. Huang, M. Dong, J. Liu, et al., Concise syntheses of trifluoromethylated cyclic and acyclic analogues of cADPR, Molecules 15 (2010) 8689-8701.
|
[5] |
B.V.L. Potter, T.F. Walseth, Medicinal chemistry and pharmacology of cyclic ADPribose, Curr. Mol. Med. 4 (2004) 303-311.
|
[6] |
J. Xu, Z.J. Yang, W. Dammermann, et al., Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains, J. Med. Chem. 49 (2006) 5501-5512.
|
[7] |
A.H. Guse, Second messenger function and the structure-activity relationship of cyclic adenosine diphosphoribose (cADPR), FEBS. J. 272 (2005) 4590-4597.
|
[8] |
S. Shuto, M. Fukuoka, A. Manikowsky, et al., Total synthesis of cyclic ADPcarbocyclic-ribose, a stable mimic of Ca2+-mobilizing second messenger cyclic ADP-ribose1, J. Am. Chem. Soc. 123 (2001) 8750-8759.
|
[9] |
M. Dong, T. Kirchberger, X.C. Huang, et al., Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoro-methyl-N1-[(5''-O-phosphorylethoxy)methyl]-50-O-phosphorylinosine-50,500-cyclic-pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells, Org. Biomol. Chem. 8 (2010) 4705-4715.
|
[10] |
F.J. Zhang, S. Yamada, Q.M. Gu, C.J. Sih, Synthesis and characterization of cyclic ATP-ribose: a potent mediator of calcium release, Bioorg. Med. Chem. Lett. 6 (1996) 1203-1208.
|
[11] |
N. Qi, K. Jung, M. Wang, et al., A novel membrane-permeant cADPR antagonist modified in the pyrophosphate bridge, Chem. Commun. 47 (2011) 9462-9464.
|
[12] |
X. Gu, Z.J. Yang, L.R. Zhang, et al., Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5''-O-phosphorylethoxy) methyl]-5'-O-phosphoryl-inosine 5',5''-cyclic-pyrophosphate (cIDPRE) and 8-substituted derivatives, J. Med. Chem. 47 (2004) 5674-5682.
|
[13] |
R. Aarhus, K. Gee, H.C. Lee, Caged cyclic ADP-ribose synthesis and use, J. Biol. Chem. 270 (1995) 7745-7749.
|
[14] |
A.H. Guse, X.F. Gu, L.R. Zhang, et al., A minimal structural analogue of cyclic ADPribose synthesis and calcium release activity in mammalian cells, J. Biol. Chem. 280 (2005) 15952-15959.
|
[15] |
J.Wang, J. Zhou, G.P. Donaldson, et al., Conservative change to the phosphatemoiety of cyclic diguanylicmonophosphate remarkably affects its polymorphismand ability to bind DGC, PDE, and PilZ proteins, J Am. Chem. Soc. 133 (2011) 9320-9330.
|
[16] |
E. Krawczyk, J. Mikolajczak, A. Skowronska, J. Michalski, Reaction of tricoordinate phosphorus compounds with organophosphorus pseudohalogens: desulfurization and deoxygenation of oxophosphoranesulfenyl chlorides, scope and mechanism, J. Org. Chem. 57 (1992) 4963-4970.
|
[17] |
L.X. Na, X.L. Sun, M. Wang, et al., Atropisomerism of diastereomer diribonucleoside phosphotriester, Chin. Chem. Lett. 24 (2013) 13-16.
|
|
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