固体丁酸类代谢物13C化学位移的结构依赖性

波谱学杂志 ›› 2012, Vol. 29 ›› Issue (2): 231-238.

固体丁酸类代谢物¹³C化学位移的结构依赖性

任萍萍^1,2，黄静^1,2，张利民¹，唐惠儒^1*

1. 波谱与原子分子物理国家重点实验室，武汉磁共振中心(中国科学院武汉物理与数学研究所)，湖北武汉 430071;
2. 中国科学院研究生院，北京 100049

收稿日期:2011-05-12 修回日期:2011-06-01 出版日期:2012-06-05 发布日期:2012-06-05
基金资助:
国家自然科学基金资助项目(20825520, 20903115, 20921004)；国家蛋白质重大科学研究计划资助项目（2007CB914701, 2010CB912501）.

Structural Dependence of ¹³C Chemical Shifts in Solid Hydroxy- and Amino-Butyrate Metabolites

REN Ping-Ping^1,2, HUANG Jing^1,2, ZHANG Li-Min¹, TANG Hui-Ru^1*

1. State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Center of Magnetic Resonance (Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences), Wuhan 430071, China; 
2. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China

Received:2011-05-12 Revised:2011-06-01 Online:2012-06-05 Published:2012-06-05
Supported by:
国家自然科学基金资助项目(20825520, 20903115, 20921004)；国家蛋白质重大科学研究计划资助项目（2007CB914701, 2010CB912501）.

摘要/Abstract

摘要：

丁酸类代谢物广泛存在于动物、植物和微生物中，且具有多种重要的生理功能，但它们的固体核磁共振参数、分子动力学性质及其结构依赖性并未得到清楚的认识. 该文使用高分辨交叉极化与魔角旋转核磁共振（¹³C CPMAS）实验技术，分析了一系列固体丁酸类代谢物的¹³C化学位移，发现了这些代谢物的¹³C化学位移与其分子结构的一些相关性规律. 另外还发现，固体丁酸类代谢物与其在溶液中的¹³C化学位移有显著的差异. 这些代谢物中甲基参与的疏水作用以及羟基、氨基和羧基参与的氢键作用均对其化学位移大小有重要的影响. 上述结果为认识代谢物的结构和功能以及功能对结构的依赖性提供了重要信息.

关键词: 固体核磁共振（solid-state NMR), 氨基丁酸, 羟基丁酸, ¹³C 化学位移, 结构依赖性

Abstract:

Butyrate metabolites are present in animals, plants and some microorganisms with various important biological functions. Many molecular features of the metabolites remain to be fully understood, including the characteristics of their structures in the solid states, molecular dynamics and the relationships between these two aspects. In this paper, the ¹³C chemical shifts of a series of amino- and hydroxylbutyrate metabolites were analyzed with ¹³C CP MAS NMR spectroscopy. Some structure-property relationships were observed. These metabolites had significant differences for their ¹³C chemical shifts in solution and the solid state. In the solid state, the presence of amino and hydroxyl groups had obvious contributions to such differences due to their participation in hydrogen-bonding whereas participation of methyl groups in hydrophobic interactions also had observable effects. These findings provide essential basic information for further understanding the structures, molecular dynamics and perhaps polymorphisms for these metabolites.

Key words: solid-state NMR, aminobutyrate, hydroxybutyrate, ¹³C chemical shift, structure-property relationship

中图分类号:

O482.53

任萍萍, 黄静, 张利民, 唐惠儒. 固体丁酸类代谢物¹³C化学位移的结构依赖性[J]. 波谱学杂志, 2012, 29(2): 231-238.

REN Ping-Ping, HUANG Jing, ZHANG Li-Min, TANG Hui-Ru. Structural Dependence of ¹³C Chemical Shifts in Solid Hydroxy- and Amino-Butyrate Metabolites[J]. Chinese Journal of Magnetic Resonance, 2012, 29(2): 231-238.

参考文献

[1] Pan J W, Rothman D L, Behar K L, et al. Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis[J]. J Cerebr Blood F Met, 2000, 20: 1 502-1 507.

[2] Walsh J M, Bowery N G, Brown D A, et al. Metabolism of gamma-aminobutyric acid (GABA) by peripheral nervous-tissue[J]. J Neurochem, 1974, 22: 1 145-1 147.

[3] Ignatov Yu D, Andreev B V, Makarova E P, et al. Effect of pain caused by bone tissue multiple injury on gamma-aminobutyric acid metabolism and functional condition of animals[J]. Patol Fiziol Eksp Ter, 1989, 1: 11-14.

[4] Zhang L M, Tang H R, Hou G J, et al. The domain structure and mobility of semi-crystalline poly (3-hydroxybutyrate) and poly (3-hydroxybutyrateco-3-hydroxyvalerate): A solid-state NMR study[J]. Polymer, 2007, 48: 2 928-2 938.

[5] Ding D W, Ding Y R, Cai Y J, et al. Exploring poly-beta-hydroxybutyrate metabolism through network-based extreme pathway analysis[J]. Rivista Di Biologia-Biology Forum, 2008, 101: 67-79.

[6] Xiao C N, Hao F H, Qin X R, et al. An optimized buffer system for NMR-based urinary metabonomics with effective pH control, chemical shift consistency and dilution minimization[J]. Analyst, 2009, 134: 916-925.

[7] Tang H R, Belton P S. Molecular motions of D-alpha-galacturonic acid (GA) and methyl D-alpha-galacturonic acid methyl ester (MGAM) in the solid state A proton NMR study [J]. Solid State Nucl Magn Reson, 1998, 12: 21-30.

[8] Tang H R, Wang Y L, Belton P S. Molecular motions of alpha L-rhamnopyranose and methyl alpha L-rhamnopyranoside in the glassy and crystalline states: A proton NMR study [J]. Phys Chem Chem Phys, 2004, 6: 3 694-3 701.

[9] Wang Y L, Tang H R, Belton P S. Solid state NMR studies of the molecular motions in the polycrystalline alpha L-fucopyranose and methyl alpha L-fucopyranoside[J]. J Phys Chem B, 2002, 106: 12 834-12 840.

[10] Ren P, Reichert D, He Q, et al. Understanding the molecular dynamics associated with polymorphic transitions of DL-norvaline with solid-state NMR methods[J]. J Phys Chem B, 2011, 115: 2 814-2 823.

[11] Hirokawa S, Kuribayashi S, Nitta I. The crystal structure of alpha-amino-isobutyric acid[J]. Bull Chem Soc Jpn, 1952, 25: 192-195.

[12] Ichikawa T, Iitaka Y. Crystal structures of DL-alpha-amino n-butyric acid[J]. Acta Cryst B, 1968, 24: 1 488-1 501.

[13] Gaykema W P J, Kanters J A, Roelofsen G. Crystal structure of α-hydroxyisobutyric acid[J]. Acta Cryst C, 1978, 7: 463-466.

[14] Dobson A J, Gerkin R E. DL-3-aminoisobutyric acid monohydrate[J]. Acta Cryst C, 1998, 54: 972-974.

[15] Weber H P, Craven B M, McMullan R K. γ-aminobutyric acid[J]. Acta Cryst B, 1983, 39: 360-362.

[16] Schilf W, Kamienski B, Kolodziej B, et al. The NMR study of hydrogen bond formation in some tris {[( salicylidene) amino] ethyl} amine derivatives in solution and in the solid state[J]. J Mol Struct, 2004, 708: 33-38.

[17] Odgaard L, Bak M, Jakobsen H J, et al. ¹³C chemical shift and ¹³C-¹⁴N dipolar coupling tensors determined by ¹³C rotary resonance solid-state NMR[J]. J Magn Reson, 2001, 148: 298-308.

[18] Tang H R, Belton P S. Molecular dynamics of polycrystalline cellobiose studied by solid-state NMR[J]. Solid State Nucl Magn Reson, 2002, 21: 117-133.

[19] Wang Y L, Belton P S, Tang H R, et al. Solid state NMR, IR and X-ray diffraction studies of the structure and motion of L-leucinamide[J]. J Chem Soc, Perkin Trans 2, 1997. 899-904.

固体丁酸类代谢物¹³C化学位移的结构依赖性

Structural Dependence of ¹³C Chemical Shifts in Solid Hydroxy- and Amino-Butyrate Metabolites

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	花蕊, 孙钰, 温林飞, 刘慧, 万遂人. 在体检测γ-氨基丁酸的MEGA-PRESS序列优化设计[J]. 波谱学杂志, 2018, 35(2): 188-197.
[2]	李东北, 许帅, 喻志武. 固体核磁共振技术在骨基生物材料研究中的应用[J]. 波谱学杂志, 2017, 34(1): 115-129.
[3]	陈梅泞, 王前锋, 李改英, 张竹伟, 陈录广, 李建奇. 人脑GABA磁共振波谱测量中大分子影响的研究[J]. 波谱学杂志, 2016, 33(4): 618-626.
[4]	张竹伟1，陈录广2，裴孟超3，李建奇1. 人脑 GABA-MRS* 中回顾性运动校正方法研究 [J]. 波谱学杂志, 2015, 32(4): 596-605.
[5]	徐玮婧，刘清华，胡炳文*，陈群. 聚氧乙烯-六氟砷酸锂复合物不同结晶结构的¹³C谱归属[J]. 波谱学杂志, 2015, 32(3): 399-408.
[6]	唐新启1,2，张正逢1，杨俊1*. 生物固体核磁共振中样品发热的研究进展[J]. 波谱学杂志, 2015, 32(1): 123-140.
[7]	罗欢1,2，梁欣苗1,2，冯继文1，王立英1. 结晶型PEO8∶NaPF6聚电解质中晶区链段的运动[J]. 波谱学杂志, 2015, 32(1): 12-22.
[8]	刘源，陈胜利，吴强，陈铁红，孙平川. 固体NMR 研究PMMA 纳米复合材料结构与受限链运动[J]. 波谱学杂志, 2015, 32(1): 23-32.
[9]	郑慧，韩明月，胡炳文，杨光. 不同采样模式的固体DQ-SQ 实验的压缩感知重建比较[J]. 波谱学杂志, 2014, 31(4): 535-547.
[10]	李博解，徐君，王强，王秀梅，齐国栋，邓风. 铜丝光沸石上甲醇羰基化反应的固体核磁共振研究[J]. 波谱学杂志, 2014, 31(3): 331-340.
[11]	陈录广，李建奇*，王前锋. 人脑GABA测量在临床3 T磁共振成像系统上的实现[J]. 波谱学杂志, 2013, 30(3): 345-353.
[12]	张正逢1,2，杨俊1*. 固体核磁共振研究淀粉样蛋白纤维的进展[J]. 波谱学杂志, 2013, 30(2): 157-174.
[13]	黄静, 唐惠儒. 自旋弛豫时间测定对固体代谢物分子动力学性质的研究[J]. 波谱学杂志, 2012, 29(4): 605-620.
[14]	张荣纯, 孙平川. 先进固体NMR技术研究高分子结构与动力学[J]. 波谱学杂志, 2012, 29(3): 307-338.
[15]	Joel A.Tang, 傅日强. 超强边缘磁场梯度场下的磁共振成像：STRAFI实验[J]. 波谱学杂志, 2012, 29(3): 419-445.