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王可可, 梁宇, 陈希, 姜明燕. 氨基酸衍生物类凝胶因子的合成及成胶能力评价[J]. 中国药科大学学报, 2014, 45(3): 320-324. DOI: 10.11665/j.issn.1000-5048.20140312
引用本文: 王可可, 梁宇, 陈希, 姜明燕. 氨基酸衍生物类凝胶因子的合成及成胶能力评价[J]. 中国药科大学学报, 2014, 45(3): 320-324. DOI: 10.11665/j.issn.1000-5048.20140312
WANG Keke, LIANG Yu, CHEN Xi, JIANG Mingyan. Synthesis and gelation ability assessment of amino acid derivative gelators[J]. Journal of China Pharmaceutical University, 2014, 45(3): 320-324. DOI: 10.11665/j.issn.1000-5048.20140312
Citation: WANG Keke, LIANG Yu, CHEN Xi, JIANG Mingyan. Synthesis and gelation ability assessment of amino acid derivative gelators[J]. Journal of China Pharmaceutical University, 2014, 45(3): 320-324. DOI: 10.11665/j.issn.1000-5048.20140312

氨基酸衍生物类凝胶因子的合成及成胶能力评价

Synthesis and gelation ability assessment of amino acid derivative gelators

  • 摘要: 以L-丙氨酸和L-苯丙氨酸为母体,与不同碳链长度的饱和酰氯进行酰胺反应,合成了一系列有机凝胶因子,并通过1H NMR和MS对其结构进行鉴定。通过测定最小胶凝浓度和相转变温度,比较凝胶因子分子结构与胶凝能力间的关系,结果表明,8种凝胶因子均可在大多数油相中形成有机凝胶,氨基酸手性碳原子的空间位阻及羧酸端酯基的增大均可导致胶凝能力的下降,而碳链长度的增加则使有机凝胶胶凝能力增强。有机凝胶因子分子结构对胶凝能力影响规律的发现为开发新型有机凝胶释药系统提供了理论基础。

     

    Abstract: A series of amino acid derivative gelators based on carbonyl chloride with different carbon chain lengths were synthesized using L-alanine and L-phenylalanine as precursors. The structures of the products were verified by FT-IR, 1H NMR and MS, respectively. In order to investigate the correlations between gelation ability and molecular structure, minimum gelation concentrations of organogelators and gel-sol transition temperatures of organogels were determined. The results indicated that: (i)these eight organogelators could produce gel in most oils; (ii)the increase of the amino acids chiral carbon atom steric hindrance and esterification degree of carboxylic acid group could lead to the decline of gelation ability; (iii)and the increase of carbon-chain length could strengthen the gelation ability. Overall, the relation between the gelator chemical structure and its gelation ability established during our work provides a theoretical basis for the development of a new organogel drug delivery system.

     

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