| Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides | |
| Hou JL(侯军利) ; Shao XB(邵学斌) ; Chen GJ(陈光巨) ; Zhou YX(周艳霞) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭) | |
| 刊名 | J. Am. Chem. Soc.
 |
| 2004 | |
| 卷号 | 126期号:39页码:12386-12394 |
| ISSN号 | 0002-7863 |
| 其他题名 | 氢键驱动的寡聚肼酰胺及其对糖的识别作用 |
| 通讯作者 | 黎占亭 |
| 英文摘要 | This paper describes the synthesis and characterization of the first series of hydrogen bonding-driven hydrazide foldamers and their recognition for alkyl saccharides in chloroform. Oligomers 1, 2-4, 5, 6, and 7, which contain one, two, four, six, or twelve repeated dibenzoyl hydrazide residues, respectively, have been prepared. The rigid and planar conformations of 1 and 2 or 4 have been established with X-ray analysis and H-1 NMR spectroscopy, whereas the folding and helical conformations of 5-7 have been evidenced by the 1D and 2D H-1 NMR and IR spectroscopy and molecular mechanics calculations. Molecular mechanics calculations also revealed that 5, 6, and 7 possess a rigid cavity with size of ca. 10.6 to 11.1 Angstrom, and half of the carbonyl groups in the folding conformations are orientated inwardly inside the cavity. H-1 NMR and CD experiments revealed that 5-7 efficiently complex alkylated mono- and disaccharides 32-35 in chloroform. The association constants (K-assoc) of the complexes have been determined with the H-1 NMR and fluorescent titration methods. The energy-minimized conformation of 6(.)34 has been obtained with molecular mechanics calculation. The hydrazide-based folding structures described here represent novel examples of hydrogen bonding-driven foldamers that act as artificial receptors for selective molecular recognition. |
| 学科主题 | 物理有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/ja047430p |
| 语种 | 英语 |
| WOS记录号 | WOS:000224219900059 |
| 公开日期 | 2013-01-16 |
| 内容类型 | 期刊论文 |
| 源URL | [http://202.127.28.38/handle/331003/12648]  |
| 专题 | 上海有机化学研究所_物理有机化学研究室 |
| 推荐引用方式 GB/T 7714 | Hou JL,Shao XB,Chen GJ,et al. Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides[J]. J. Am. Chem. Soc.,2004,126(39):12386-12394. |
| APA | 侯军利,邵学斌,陈光巨,周艳霞,蒋锡夔,&黎占亭.(2004).Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides.J. Am. Chem. Soc.,126(39),12386-12394. |
| MLA | 侯军利,et al."Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides".J. Am. Chem. Soc. 126.39(2004):12386-12394. |
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