Citation: Lu-Xin Na, Xu-Lin Sun, Meng Wang, Kun-Feng Li, Lei Xing, Zhuo Chen, Zhu Guan, Zhen-Jun Yang. Atropisomerism of diastereomer diribonucleoside phosphotriester[J]. Chinese Chemical Letters, ;2013, 24(01): 13-16. shu

Atropisomerism of diastereomer diribonucleoside phosphotriester

1.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

Corresponding author: Zhen-Jun Yang,
Received Date: 23 November 2012
Available Online: 20 December 2012

Linear diribonucleoside phosphotriester is an important intermediate for synthesizing biologically important compounds,such as cyclic bis(3'-5')diguanylic acid(c-di-GMP)and its analogues. Atropisomerism of diastereomers generated by the chiral center of the P atom,which results in the doubling of signals in ³¹P NMR.The data of ³¹P NMR at different temperature are presented,and thereafter the reason is discussed.
- Diribonucleoside phosphotriester,
- Atropisomer,
- ³¹P NMR
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  [10] Compound 1: ¹H NMR(400 MHz,DMSO-d₆): δ 12.07-12.05(m,8H),11.75-11.73 (m,4H),11.65-11.61(m,4H),8.29-8.25(m,8H),5.89-5.82(m,8H),4.83-4.79(m, 8H),4.67-2.90(m,32H),2.19-2.18(m,48H),0.92-0.62(m,72H),0.15-0.28(m, 48H). ³¹P NMR(162.0 MHz,DMSO-d₆,decoupled with¹H): δ 25 ℃:1.77(s),1.84 (s),1.94(s);@20 ℃ 1.77(s),1.83(s),1.94(s);@30 ℃:1.77(s),1.82(s),1.85(s), 1.95(s);@40 ℃:1.78(s),1.83(s),1.88(s),1.96(s);@60 ℃:1.81(s),1.84(s),1.93 (s),1.99(s).(CD3CN,162.0 MHz,decoupled with¹H): δ 2.30(s),2.41(s),2.70(s); MS(ESI)m/z:994.5[M+H] ⁺,1016.5[M+Na] ⁺.Compound 2: ³¹P NMR(162 MHz, DMSO-d₆): δ 2.43(s),2.45(s),2.52(s);MS(ESI)m/z:910.2[M+H] ⁺. Compound 3: ³¹P NMR(162 MHz,DMSO-d₆): δ 2.46(s),2.49(s),2.54(s), 2.56(s);MS(ESI)m/z:928.2[M+H] ⁺.Compound 4a: ³¹P NMR(162 MHz,DMSO-d6): δ 67.46(s),67.41(s);MS(ESI)m/z:1010.3[M+H] ⁺.Compound 4b: 31P NMR (162 MHz,DMSO-d₆): δ 67.69(s),67.50(s);MS(ESI)m/z:1010.3[M+H] ⁺.
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沈阳化工大学材料科学与工程学院沈阳 110142