Page 81 - 《精细化工》2021年第10期
P. 81
第 10 期 李亚楠,等: 香豆素基金属-有机笼对氨基葡萄糖的识别 ·2011·
3 结论 [13] DUAN H H, LI Y W, CAO L P, et al. Host-guest recognition and
fluorescence of a tetraphenylethene-based octacationic cage[J].
Angewandte Chemie International Edition, 2020, 59(25): 10101-
(1)设计合成了含有香豆素功能基团的有机配 10110.
体 H 3 L,通过与 Zn(Ⅱ)配位自组装构建了一例金属- [14] ZENG L H, XIAO Y L, JIANG J X, et al. Hierarchical gelation of a
Pd 12L 24 metal-organic cage regulated by cholesteryl groups[J].
有机笼状化合物 Zn-L,并通过紫外-可见吸收光谱和 Inorganic Chemistry, 2019, 58(15): 10019-10027.
高分辨质谱表征其为 M 6 L 4 的笼状结构。 [15] CAO D X, LIU Z Q, VERWILST P, et al. Coumarin-based
small-molecule fluorescent chemosensors[J]. Chemical Reviews,
(2)质谱结果表明,Zn-L 与氨基葡萄糖形成了
2019, 119(18): 10403-10519.
物质的量比为 1∶2 的主客体包合物,并且荧光滴定 [16] DU W (杜微), YANG Q W (杨秋云), JIA C M (贾春满), et al.
结果表明,Zn-L 与氨基葡萄糖的结合常数为 1.6× Synthesis and mechanism of multi-ion recognition fluorescence
probe[J]. Fine Chemicals (精细化工), 2017, 34(10): 1119-1125.
8
2
2
10 L /mol ,显示出主客体物种在溶液中高度的稳定性。 [17] FENG H J, LI R R, SONG Y C, et al. Novel D-π-A-π-A coumarin
(3)Zn-L 能够通过氢键作用在 9 种糖类小分子 dyes for highly efficient dye-sensitized solar cells: Effect of π-bridge
on optical, electrochemical, and photovoltaic performance[J]. Journal
中特异性识别氨基葡萄糖,以荧光淬灭的方式输出 of Power Sources, 2017, 345: 59-66.
识别信号,并且能够应用于细胞中氨基葡萄糖的荧 [18] LONG L L, HUANG M Y, WANG N, et al. A mitochondria-specific
fluorescent probe for visualizing endogenous hydrogen cyanide
光成像。在相同条件下,配体 H 3 L 对氨基葡萄糖没 fluctuations in neurons[J]. Journal of the American Chemical Society,
有识别效果,表明金属-有机笼状空腔对识别作用至 2018, 140(5): 1870-1875.
[19] WU J S, LIU W M, ZHUANG X Q, et al. Fluorescence turn on of
关重要。
coumarin derivatives by metal cations: A new signaling mechanism
based on C==N isomerization[J]. Organic Letters, 2007, 9(1): 33-36.
参考文献: [20] XU X Q, WANG Z, LI R, et al. A degradable and recyclable
[1] SOLANKIA A, DAS M, THAKORE S. A review on carbohydrate photothermal conversion polymer[J]. Chemistry-A European Journal,
embedded polyurethanes: An emerging area in the scope of 2018, 24(39): 9769-9772.
biomedical applications[J]. Carbohydrate Polymers, 2018, 181: 1003- [21] HE C, LIN Z H, HE Z, et al. Metal-tunable nanocages as artificial
1016. chemosensors[J]. Angewandte Chemie International Edition, 2008,
47(5): 877-881.
[2] GALLINGER A, BIET T, PETERS T, et al. Insights into neuronal [22] ZHAO L, WEI J W, LU J H, et al. Renewable molecular flasks with
cell metabolism using NMR spectroscopy: Uridyl diphosphate
NADH models: Combination of light-driven proton reduction and
n-acetyl-glucosamine as a unique metabolic marker[J]. Angewandte
biomimetic hydrogenation of benzoxazinones[J]. Angewandte
Chemie International Edition, 2011, 50(49): 11672-11674. Chemie, 2017, 129(30): 8818-8822.
[3] GAGARINOV I A, LI T H, BOONS G J, et al. Protecting-group- [23] CONNORS K A. Binding constants[M]. New York: John Wiley ,
controlled enzymatic glycosylation of oligo-N-acetyllactosamine 1987.
derivatives[J]. Angewandte Chemie International Edition, 2019, [24] JING L, JI G F, LIU Z L, et al. Uitrastable 1D europium complex for
58(31): 10547-10552. simultaneous and quantitative sensing of Cr (Ⅲ) and Cr (Ⅵ) ions in
[4] LABORDA P, LYU Y M, VOGLMEIR J, et al. An enzymatic aqueous solution with high selectivity and sensitivity[J]. Inorganic
N-acylation step enables the biocatalytic synthesis of unnatural Chemistry, 2017, 56: 4197-4205.
sialosides[J]. Angewandte Chemie International Edition, 2020, [25] WU X, HE C, WU X, et al. An L-proline functionalized metallo-
59(13): 5308-5311. organic triangle as size-selective homogeneous catalyst for
[5] ZHAO S F (赵胜芳), CHEN N Y (陈年友), LI Z Y (李早英), et al. asymmetry catalyzing aldol reactions[J]. Chemical Communications,
Synthesis of meso-tetra(4-carboxylphenyl)porphyrin and metal 2011, 47(29): 8415-8417.
complex and the selective recognition with carbohydrates[J]. Chinese [26] SHEN Y, SHEN M L, WANG P S. Light-mediated chiral phosphate
Journal of Organic Chemistry (有机化学), 2010, 30(12): 1903-1898. catalysis for asymmetric dicarbofunctionalization of enamides[J].
[6] RIOS P, MOOIBROEK T J, DAVIS A P, et al. Enantioselective ACS Catalysis, 2020, 10(15): 8247-8253.
carbohydrate recognition by synthetic lectins in water[J]. Chemical [27] ZHAO L, JING X, LI X Z, et al. Catalytic properties of chemical
Science, 2017, 8(5): 4056-4061. transformation within the confined pockets of werner-type
[7] FRANCESCONI O, MARTINUCCI M, ROELENS S, et al. A capsules[J]. Coordination Chemistry Reviews, 2019, 378: 151-187.
biomimetic synthetic receptor selectively recognising fucose in water[J]. [28] GAO X (高昕), JIA L H (贾丽华), YANG R (杨瑞), et al. Quinoline
3+
Chemistry-A European Journal, 2018, 24(26): 6828-6836. derivative with fluorescent off-on function for Fe and oxalic
acid[J]. Fine Chemicals (精细化工), 2020, 37(10): 2015-2020.
[8] MOOIBROEK T J, HARNIMAN R L, DAVIS A P, et al. A threading
[29] LI Y C, LI X Z, LI L, et al. Phenoxazine-based supramolecular
receptor for polysaccharides[J]. Nature Chemistry, 2016, 8(1): 69-74.
[9] PALANICHAMY K, BRAVO M F, BRAUNSCHWEIG A B, et al. tetrahedron as biomimetic lectin for glucosamine recognition[J].
Chinese Chemical Letters, 2021, 32(2): 735-739.
Binding studies on a library of induced-fit synthetic carbohydrate [30] KE C, DESTECROIX H, CRUMP M P, et al. A simple and
receptors with mannoside selectivity[J]. Chemistry-A European accessible synthetic lectin for glucose recognition and sensing[J].
Journal, 2018, 24(52): 13971-13982. Nature Chemistry, 2012, 4(9): 718-723.
[10] TROMANS R A, CARTER T S, DAVIS A P, et al. A biomimetic [31] FRANCESCONI O, GENTILI M, ROELENS S. Synthetic tripodal
receptor for glucose[J]. Nature Chemistry, 2019, 11(1): 52-56. receptors for carbohydrates. Pyrrole, a hydrogen bonding partner for
[11] LEE H, KIM D, JUNG O S, et al. Molecular balloon, Pd 6L 8 cages: saccharidic hydroxyls[J]. The Journal of Organic Chemistry, 2012,
Recognition of alkyl sulfate surfactants[J]. Chemical Communication, 77(17): 7548-7554.
2020, 56(19): 2841-2844. [32] VONGNAM K, MUANGNOI C, ROJSITTHISAK P, et al. A highly
[12] BRAVIN C, BADETTI E, ZONTA C, et al. Triggering assembly and selective turn-on fluorescent sensor for glucosamine from
disassembly of a supramolecular cage[J]. Journal of the American amidoquinoline-napthalimide dyads[J]. Biosensors and Bioelectronics,
Chemical Society, 2017, 139(18): 6456-6460. 2016, 86: 472-476.