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通过振动圆二色性确定溴化倍半萜的绝对构型。

Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism.

作者信息

Monde Kenji, Taniguchi Tohru, Miura Nobuaki, Vairappan Charles S, Suzuki Minoru

机构信息

Division of Biological Sciences, Graduate School of Science, Frontier Research Center for the Post-Genomic Science and Technology, Hokkaido University, Sapporo 001-0021, Japan.

出版信息

Chirality. 2006 May 15;18(5):335-9. doi: 10.1002/chir.20259.

Abstract

Two brominated sesquiterpenes, majapolene B (1) and acetylmajapolene B (2), isolated from the red algal genus Laurencia were investigated using vibrational circular dichroism (VCD). The ab initio theoretical VCD and IR calculations of 1 and 2 were performed by density functional theory (DFT) using the B3PW91/6-31G(d,p) basis set. The experimental VCD spectra and corresponding population-weighted theoretical VCD spectra were found to be in excellent agreement in CCl(4) solution in the 1800-850 cm(-1) region, which allowed unambiguous determination of the absolute configurations of (-)-1 and (-)-2 as 7S,10S and 7S,10S, respectively.

摘要

从红藻劳伦藻属中分离出的两种溴化倍半萜,马贾波烯B(1)和乙酰马贾波烯B(2),使用振动圆二色性(VCD)进行了研究。采用密度泛函理论(DFT),以B3PW91/6-31G(d,p)基组对1和2进行了从头算理论VCD和红外计算。发现在四氯化碳溶液中1800 - 850 cm⁻¹区域,实验VCD光谱与相应的总体加权理论VCD光谱高度吻合,这使得能够明确确定(-)-1和(-)-2的绝对构型分别为7S,10S和7S,10S。

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