用于手性识别α-氨基酸的方酰胺荧光探针分子
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摘要
以天然氨基酸为手性原料合成了4种新型的手性方酰胺荧光探针分子(5～8),该合成路线简短,后处理简单,无需柱层析纯化.以荧光光谱为检测手段,测试了此类探针分子对苯丙氨酸、缬氨酸和脯氨酸的手性识别效果,结果表明,探针分子5可以有效识别苯丙氨酸的2个对映异构体.当加入L-苯丙氨酸后,探针分子5的荧光强度显著增强,而加入D-苯丙氨酸后探针分子5的荧光强度显著减弱,2种异构体的荧光强度比(I_L/I_D)可达2. 4.
Four novel squaramide fluorescence probes were synthesised using natural amino acids as chiral sources, which featuers concise synthetic route, simple work-up and purification without column chromatography. The chiral recognition effects of these squaramide probes for phenylalanine,valine and proline were tested using fluorescence spectrum,which indicated that probe 5 could effectively discriminate two enantiomers of phenylalanine. The fluorescence intensity of probe 5 was remarkably enhanced after adding L-phenylalanine; on the contrary,it was observably reduced when D-phenylalanine was added,and the fluorescence intensity ratio of two enantiomers( I_L/I_D) was up to 2. 4.
Four novel squaramide fluorescence probes were synthesised using natural amino acids as chiral sources, which featuers concise synthetic route, simple work-up and purification without column chromatography. The chiral recognition effects of these squaramide probes for phenylalanine,valine and proline were tested using fluorescence spectrum,which indicated that probe 5 could effectively discriminate two enantiomers of phenylalanine. The fluorescence intensity of probe 5 was remarkably enhanced after adding L-phenylalanine; on the contrary,it was observably reduced when D-phenylalanine was added,and the fluorescence intensity ratio of two enantiomers( I_L/I_D) was up to 2. 4.
引文
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[3] Chen H.,LüX. Y.,Huang J. M.,Gao R. Y.,Wang Q. S.,Chem. J. Chinese Universities,2000,21(4),562—565(陈慧,吕宪禹,黄君珉,高如瑜,王琴孙.高等学校化学学报,2000,21(4),562—565)
[4] Huang J. M.,Chen H.,Gao R. Y.,Wang Q. S.,Chem. J. Chinese Universities,2001,22(11),1838—1842(黄君珉,陈慧,高如瑜,王琴孙.高等学校化学学报,2001,22(11),1838—1842)
[5] Busschaert N.,Caltagirone C.,van Rossom W.,Gale P. A.,Chem. Rev.,2015,115,8038—8155
[6] Saleem M.,Lee K.H.,RSC Adv.,2015,5,72150—72287
[7] Dong W. K.,Akogun S. F.,Zhang Y.,Sun Y. X.,Dong X. Y.,Sens. Actuators B,2017,238,723—734
[8] Zhou J. J.,Song X. Q.,Liu Y. A.,Wang X. L.,RSC Adv.,2017,7,25549—25559
[9] Yu B.,Li C. Y.,Sun Y. X.,Jia H. R.,Guo J. Q.,Li J.,Spectrochim. Acta A,2017,184,249—254
[10] Dong W. K.,Li X. L.,Wang L.,Zhang Y.,Ding Y. J.,Sens. Actuators B,2016,229,370—378
[11] Hu J. H.,Sun Y.,Qi J.,Li Q.,Wei T. B.,Spectrochim. Acta A,2017,175,125—133
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[13] Pu L.,Chem. Rev.,2004,104,1687—1716
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[17] Liu H. L.,Peng Q.,Wu Y. D.,Chen D.,Hou X. L.,Sabat M.,Pu L.,Angew. Chem. Int. Ed.,2010,49,602—606
[18] Folmer-Andersen J. F.,Lynch V. M.,Anslyn E. V.,J. Am. Chem. Soc.,2005,127,7986—7987
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[22] Zhao J.,Fyles T. M.,James T. D.,Angew. Chem. Int. Ed.,2004,43,3461—3464
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[25] Song F.,Wei G.,Wang L.,Jiao J.,Cheng Y.,Zhu C.,J. Org. Chem.,2012,77,4759—4764
[26] Folmer-Andersen J. F.,Lynch V. M.,Anslyn E. V.,J. Am. Chem. Soc.,2005,127,7986—7987
[27] Chen X.,Huang Z.,Chen S.,Li K.,Yu X.,Pu L.,J. Am. Chem. Soc.,2010,132,7297—7299
[28] Albrecht.,Dickmeiss G.,Acosta F. C.,Rodríguez-Escrich C.,Davis R. L.,Jrgensen K. A.,J. Am. Chem.Soc.,2012,134,2543—2546
[29] Malerich J. P.,Hagihara K.,Rawal V. H.,J. Am. Chem. Soc.,2008,130,14416—14417
[30] Ni X.,Wang Z.,Li X.,Cheng J. P.,Org. Lett.,2014,16,1786—1789
[31] Li Y.,Yang G. H.,He C. Q.,Li X.,Houk K. N.,Cheng J. P.,Org. Lett.,2017,19,4191—4194
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[33] Corradini R.,Paganuzzi C.,Marchelli R.,Pagliari S.,Sforza S.,Dossena A.,Galaverna G.,Duchateau A.,J. Mater. Chem.,2005,15,2741—2746
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[37] Kantharaju,Babu V. V. S.,Indian J. Chem.-Sec. B,2006,45,1942—1944