6-氨基己酸及2-氨基乙磺酸C60加成物的合成及溶解性

水溶性Fullerenes (C₆₀)衍生物的制备对于C₆₀的生物学研究具有十分重要的意义. 氨基酸与C₆₀的胺化反应可得到水溶性的氨基酸C₆₀衍生物. 以C₆₀与过量6-氨基己酸或2-氨基乙磺酸(摩尔比为1∶10)于80 ℃搅拌反应24 h, 分别得到加成度为5和4的氨基酸C₆₀主产物, 产率按加入的C₆₀计算分别为30%, 28%. 氨基酸碳链的长度及加成产物在反应体系中能否及时沉淀析出影响和控制着加成度的大小. C₆₀NH(CH₂)₅COOH]₅H₅ (3a)???, C₆₀(NHCH₂CH₂SO₃H)₄H₄ (6a)用柱层析进一步纯化, 其结构组成经元素分析, ¹H NMR, ¹³C NMR, IR所证实. 6a的水溶性受溶液pH的影响较小, 3a在不同pH缓冲溶液中的溶解性用光谱法测定, 分别为: pH＝10.25时为71.81 mg?mL^－1, pH＝7时为23.68 mg?mL^－1, pH＝3.36时为10.12 mg?mL^－1. 在波长273 nm处, 3a的摩尔消光系数为ε＝3.43×10⁴ L?mol^－1?cm^－1.

Synthesis and Solubility of 6-Aminohexanoic Acid and 2-Aminoethanesulfonic Acid C60 Adducts

Preparation of water soluble fullerenes (C₆₀) derivatives is meaningful to biological study of fullerenes. Amination reaction of amino-acid with C₆₀ led to water soluble amino-acid C₆₀ derivatives. Reaction of C₆₀ with excess of NH₂(CH₂)₅COO^－Na⁺ (1) or (4) (molar ratio is 1∶10) at 80 ℃ for 24 h afforded main amino-acid C₆₀ adducts with addition degree of 5 and 4, respectively. The yields based on the C₆₀ added were 30% and 28%, respectively. The addition degree was influenced by the length of hydrocarbon chain of amino-acid and precipitation of C₆₀ adducts from the reactant. C₆₀NH(CH₂)₅- COOH]₅H₅ (3a) and C₆₀(NHCH₂CH₂SO₃H)₄H₄ (6a) were further purified by silica column chromatography and characterized by ¹H NMR, ¹³C NMR, IR, FAB-MS spectra and elemental analysis. The solubility of 6a was less pH dependent. The solubility of 3a in water at different pH was measured by the spectro-photometric method, exhibiting solubility of 71.81 mg?mL^－1 (pH＝10.25), 23.68 mg?mL^－1 (pH＝7) and 10.12 mg?mL^－1 (pH＝3.36). The ε value of 3a at 272.8 nm was 3.43×10⁴ L?mol^－1?cm^－1.