An NMR Study of N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxycarbonyl-guanosine

doi:10.11938/cjmr20182666

Abstract

Abstract: The nucleoside derivative N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxy carbonyl-guanosine (compound 1) was obtained by selectively cleaving the 1,1,3,3-tetraisopropyldisiloxanyl protecting group at 5'-position with pyridinium hydrofluoride. Liquid chromatography-mass spectrometry (LC-MS), gas chromatography-high resolution mass spectrometry (GC-HRMS), liquid one-dimensional/two-dimensional nuclear magnetic resonance (NMR) techniques (i.e., ¹H NMR, ¹³C NMR, ¹⁹F NMR, DEPT, ¹H-¹H COSY, ¹H-¹³C HSQC and ¹H-¹³C HMBC) were used to assign the signals.

Key words: liquid NMR, chemical shift assignment, N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxycarbonyl-guanosine, deprotection, nucleoside derivative

CLC Number:

O482.53

WEI Hui-qiang, YU Jiang, BI Chang-fen, NING Hong-xin, LI Yi-liang, LIU Qiang. An NMR Study of N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxycarbonyl-guanosine[J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 93-102.

References

[1] MARKIEWICZ W, PADYUKOVA N, SAMEK Z, et al. The reaction of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane with cytosine arabinoside and 1-(6-deoxy-α-L-talofuranosyl)uracil[J]. Collect Czech Chem Commun, 1980, 45(6):1860-1865.
[2] KARPEISKY A, GONZALEZ C, BURGIN A, et al. Highly efficient synthesis of 2'-O-amino nucleosides and their incorporation in hammerhead ribozymes[J]. Tetrahedron Lett, 1998, 39(10):1131-1134.
[3] NISHIZONO N, SUMITA Y, UENO Y, et al. Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability[J]. Nucleic Acids Res, 1998, 26(22):5067-5072.
[4] HANESSIAN S, MACROTTE S, MAHARANI R, et al. Total synthesis of malayamycin A and analogues[J]. Tetrahedron, 2006, 62(22):5201-5214.
[5] ZHU X F, WILLIAMS H, SCOTT I. Aqueous trifluoroacetic acid-an efficient reagent for exclusively cleaving the 5'-end of 3',5'-TIPDS protected ribonucleosides[J]. Tetrahedron Lett, 2000, 41(56):9541-9545.
[6] WU Q P, CHEN W, WANG Y, et al. Mild, efficient and highly selective hydrolysis of acetonides with antimony trichloride[J]. Lett Org Chem, 2006, 3(4):271-274.
[7] ZHOU Z G, YUAN Y Y, LIU H B, et al. An NMR study on prucalopride[J]. Chinese J Magn Reson, 2018, 35(1):119-127. 周中高, 元洋洋, 刘红波, 等. 普卡必利的NMR研究[J]. 波谱学杂志, 2018, 35(1):119-127.
[8] SUN W, SHE M Y, ZONG C L, et al. An NMR study on diacetonefructose[J]. Chinese J Magn Reson, 2017, 34(3):329-337. 孙伟, 厍梦尧, 宗春蕾, 等. 果糖二丙酮的结构全归属[J]. 波谱学杂志, 2017, 34(3):329-337.
[9] TIMOSHCHUK V, HOGREFE R, VAGHEFI M. Improved and reliable synthesis of 3'-azido-2',3'-dideoxyguanosine derivatives[J]. Nucleosides, Nucleotides and Nucleic Acids, 2004, 23(1-2):171-181.
[10] 张正行. 有机光谱分析[M]. 北京:人民卫生出版社, 2009.

[1]	LI Ying-jun, YANG Kai-dong, JIN Kun, LIU Ji-hong, WANG Si-yuan, ZHANG Nan. NMR Study of A Novel Carbazole-Isatin Based Bis-Thiocarbohydrozone Derivative [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 83-92.
[2]	YU Gang-jin, ZHOU Zhi-ming, LV Ming, QIAN Sheng-tao, KONG Yu-hua, ZHANG Xu, MAO Shi-zhen, LIU Mai-li. Qualitative and Quantitative NMR Analysis of 1,2-Butanediol in Polymer Grade Coal-Based Ethylene Glycol [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 55-64.
[3]	ZHOU Zhong-gao, YUAN Yang-yang, HUANG Li, LIU Jin-xiang, XIE Yong-rong. Spectral Analysis of Glucose-Based Chiral N-heterocyclic Carbene Precursors [J]. Chinese Journal of Magnetic Resonance, 2018, 35(2): 215-225.
[4]	CHAI Xin, SUN Peng, YUAN Bin, XIAO Xiong-jie, ZHANG Xu, LIU Mai-li. Fast Detection of Choline Containing Compounds in Dairy Products Using NMR [J]. Chinese Journal of Magnetic Resonance, 2018, 35(2): 178-187.
[5]	SUN Wei, SHE Meng-yao, ZONG Chun-lei, GAO Xiang, GUO Juan. An NMR Study on Diacetonefructose [J]. Chinese Journal of Magnetic Resonance, 2017, 34(3): 329-337.
[6]	LI Shuang-li, ZHU Qing-jun, LIU Mai-li, YANG Yun-huang. Characteristics of Protein NMR Resonances and Chemical Shift Assignments [J]. Chinese Journal of Magnetic Resonance, 2017, 34(2): 137-147.
[7]	YU Gang-jin, LIU Jun, MAO Shi-zhen, LIU Mai-li, DU You-ru. Exchange Kinetics of Surfactants TX-100 and CTAB Investigated by ¹H NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2016, 33(3): 422-431.
[8]	ZHANG Bin-feng, ZHU Xue-rong. NMR Analyses of Two Polyether Modified Organic Silicone Surfactants [J]. Chinese Journal of Magnetic Resonance, 2016, 33(3): 432-441.
[9]	HUANG Tai-huang. Probing the Molecular Basis of SUMO-Mediated Signaling Pathway by NMR [J]. Chinese Journal of Magnetic Resonance, 2015, 32(2): 163-180.
[10]	AN Zhi-min，MA Er-qian，YANG Qiu-qing*. Structural Changes of 2-Keto-L-Gulonic Acid Studied by NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2014, 31(3): 407-414.
[11]	AN Yan-peng1,2，YANG Xiao-yan1,2，LI Hong-de1,2，LI Ning1,2，TANG Hui-ru1* . NMR Analysis of Nicotinamide N-Oxide and Pseudouridine in Rat Urine [J]. Chinese Journal of Magnetic Resonance, 2014, 31(2): 232-242.
[12]	ZHU Xin-shu1,2，CUI Jia-tao1,2，FENG Yin-gang1，ZHANG Jing-tao1，CUI Qiu1,3 . Metabolomic Analysis of Clostridium thermocellum [J]. Chinese Journal of Magnetic Resonance, 2014, 31(2): 243-252.
[13]	HUANG Jin-Cha, CHEN Feng-Lian, ZENG Yuan-Er, CAO Cheng, XU Hong-Hua. Characterization of NMR Signals of a Tirterpenoid Isolated from Radix of Ilex asprella [J]. Chinese Journal of Magnetic Resonance, 2011, 28(1): 142-152.
[14]	REN Feng-Zhi, CHEN Shu-Hong, ZHANG Xue-Xia, LI Li-Hong, GAO Yue-Qi, WANG Ning. Structure Analysis of an Oligosaccharide Isolated from Bixo orellana by NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2011, 28(1): 160-167.
[15]	YU Chong, LI Zhi-Qiang, BI Yan-Gang, SHI Xu-Dong, ZHU Lin-Li, Xia Si-Feng, LU Xi. An NMR Studies of (C₅H₁₁N₂)⁺ and (C₇H₁₂N₂)²⁺ [J]. Chinese Journal of Magnetic Resonance, 2010, 27(4): 524-531.