Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy
文献类型：期刊论文
| 作者 | Tan, Yanglan1,2; Zhao, Ning1; Stedwell, Corey N.1; Yu, Long1; Polfer, Nicolas C.1; Liu, Jinfeng3; Li, Pengfei4; , |
| 刊名 | JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
 |
| 出版日期 | 2017 |
| 卷号 | 28期号:3页码:539-550 |
| 关键词 | Lithiated N-acetyl-D-hexosamine IRMPD spectroscopy Mass spectrometry Vibrational signatures Gas-phase conformations |
| ISSN号 | 1044-0305 |
| DOI | 10.1007/s13361-016-1575-x |
| 文献子类 | Article |
| 英文摘要 | Three lithiated N-acetyl-D-hexosamine (HexNAc) isomers, N-acetyl-D-glucosamine (GlcNAc), N-acetyl-D-galactosamine (GalNAc), and N-acetyl-D-mannosamine (ManNAc) are investigated as model monosaccharide derivatives by gas-phase infrared multiple-photon dissociation (IRMPD) spectroscopy. The hydrogen stretching region, which is attributed to OH and NH stretching modes, reveals some distinguishing spectral features of the lithium-adducted complexes that are useful in terms of differentiating these isomers. In order to understand the effect of lithium coordination on saccharide structure, and therefore anomericity, chair configuration, and hydrogen bonding networks, the conformational preferences of lithiated GlcNAc, GalNAc, and ManNAc are studied by comparing the experimental measurements with density functional theory (DFT) calculations. The experimental results of lithiated GlcNAc and GalNAc show a good match to the theoretical spectra of low-energy structures adopting a C-4(1) chair conformation, consistent with this motif being the dominant conformation in condensed-phase monosaccharides. The epimerization effect upon going to lithiated ManNAc is significant, as in this case the C-1(4) chair conformers give a more compelling match with the experimental results, consistent with their lower calculated energies. A contrasting computational study of these monosaccharides in their neutral form suggests that the lithium cation coordination with Lewis base oxygens can play a key role in favoring particular structural motifs (e.g., a C-4(1) versus C-1(4)) and disrupting hydrogen bond networks, thus exhibiting specific IR spectral features between these closely related lithium-chelated complexes. |
| 学科主题 | Biochemistry & Molecular Biology ; Chemistry ; Spectroscopy |
| WOS关键词 | TANDEM MASS-SPECTROMETRY ; BETA-D-GALACTOPYRANOSE ; CRYSTAL-STRUCTURE ; D-GLUCOSAMINE ; D-GALACTOSE ; B3LYP/6-311++G-ASTERISK-ASTERISK LEVEL ; METHYL GLYCOSIDES ; NMR-SPECTROSCOPY ; HEPARAN-SULFATE ; ALPHA |
| 语种 | 英语 |
| WOS记录号 | WOS:000398111400016 |
| 出版者 | SPRINGER |
| 版本 | 出版稿 |
| 源URL | [http://202.127.25.144/handle/331004/968]  |
| 专题 | 中国科学院上海生命科学研究院营养科学研究所 |
| 作者单位 | 1.Univ Florida, Dept Chem, Gainesville, FL 32611 USA; 2.Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Nutr Sci, Shanghai 200031, Peoples R China; 3.East China Normal Univ, Inst Theoret & Computat Sci, State Key Lab Precis Spect, Shanghai 200062, Peoples R China; 4.Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA, |
| 推荐引用方式 GB/T 7714 | Tan, Yanglan,Zhao, Ning,Stedwell, Corey N.,et al. Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy[J]. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY,2017,28(3):539-550. |
| APA | Tan, Yanglan.,Zhao, Ning.,Stedwell, Corey N..,Yu, Long.,Polfer, Nicolas C..,...&,.(2017).Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy.JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY,28(3),539-550. |
| MLA | Tan, Yanglan,et al."Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy".JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY 28.3(2017):539-550. |
入库方式： OAI收割
来源：上海营养与健康研究所
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