Journal of the American Chemical Society p. 3046 - 3050 (1989)
Update date:2022-08-05
Topics:
Komiyama, Makato
Regioselective P-O(2') cleavages of 2',3'-cyclic monophosphates of cytidine (1a), uridine (1b), adenosine (1c), and guanosine (1d) to the corresponding 3'-monophosphates (IIIa-d) are achieved at pH 11.08, 20 deg C by α-cyclodextrin (α-CyD) as catalyst.The selectivities asymptotically increase with increasing concentration of α-CyD, attaining 98, 94, 76, and 67percent for the cleavages of Ia-d, respectively, at the concentration of 0.05 M α-CyD.In the absence of α-CyD, however, significant concurrent cleavages of the P-O(3') bonds take place and the selectivities for IIIa-d are only 47, 50, 54, and 52percent.The rate of the P-O(2') cleavage of Ia in the α-CyD-Ia complex is 14 times as large as that of free Ia, and the rate of the P-O(3') cleavage in the complex is virtually zero. β- and γ-CyDs show no regioselective catalyses. 1H NMR spectroscopy indicates that the α-CyD-Ia and -Ib complexes are formed by hydrogen bondings and I's are located on the secondary hydroxyl side of the cavity of α-CyD.The selective cleavages of ribonucleotide dimers CpC, CpU, CpA, and CpG to IIIa are also successfully carried out by α-CyD as catalyst.
View MoreXi'an North Information Industry Co., Ltd. Weilv Chemical Department
Contact:+86-29-88156413
Address:Jixiang Road 99 Xi'an Shaanxi Province
Contact:+33-5-34012600
Address:28 ZA des Pignès
LIAOYANG WANRONG CHEMICALS COMPANY LIMITED
Contact:86-419-2390789
Address:XINLI VILLAGE , DONG NINGWEI COUNTY,TAIZIHE DISTRICT, LIAOYANG , LIAONING
Beijing Huikang Boyuan Chemical Tech Co.,LTD
Contact:+86-10-68862197
Address:No.7 Haiying Road,Science City,Fengtai District,Beijing,China
JiangXi Hong Run Chemical Co., Ltd
Contact:+86-0791-88521351
Address:XingHuo industrial zone in YongXiu county
Doi:10.1007/s00706-019-02488-2
(2019)Doi:10.1021/acs.orglett.8b01417
(2018)Doi:10.1021/jo00350a066
(1985)Doi:10.1007/BF00833354
(1985)Doi:10.1016/j.bmcl.2003.12.041
(2004)Doi:10.1039/c8ob00601f
(2018)