Chem. J. Chinese Universities ›› 2019, Vol. 40 ›› Issue (3): 462.doi: 10.7503/cjcu20180548
• Organic Chemistry • Previous Articles Next Articles
ZHANG Ye1, WU Weihui2, ZONG Liang2, DONG Junjun2,*
Received:
2019-08-03
Online:
2019-01-12
Published:
2019-01-12
Contact:
DONG Junjun
E-mail:dongjj536@sina.com
Supported by:
CLC Number:
TrendMD:
ZHANG Ye,WU Weihui,ZONG Liang,DONG Junjun. Carbonate Handle Modified Wang Resin and Its Function†[J]. Chem. J. Chinese Universities, 2019, 40(3): 462.
Concentration/(mmol·L-1) | Abs. | Concentration/(mmol·L-1) | Abs. |
---|---|---|---|
0.0100 | 0.149 | 0.0600 | 0.672 |
0.0200 | 0.296 | 0.0700 | 0.777 |
0.0300 | 0.392 | 0.0800 | 0.872 |
0.0400 | 0.471 | 0.0900 | 0.985 |
0.0500 | 0.568 | 0.1000 | 1.051 |
Table 1 Concentration-absorbance data of Fmoc
Concentration/(mmol·L-1) | Abs. | Concentration/(mmol·L-1) | Abs. |
---|---|---|---|
0.0100 | 0.149 | 0.0600 | 0.672 |
0.0200 | 0.296 | 0.0700 | 0.777 |
0.0300 | 0.392 | 0.0800 | 0.872 |
0.0400 | 0.471 | 0.0900 | 0.985 |
0.0500 | 0.568 | 0.1000 | 1.051 |
Amino acid | Connection rate(%) | Amino acid | Connection rate(%) |
---|---|---|---|
Fmoc-Val-OH | 93.2 | Fmoc-Thr(tBu)-OH | 84.9 |
Fmoc-pro-OH | 89.1 | Fmoc-Asn(Trt)-OH | 77.0 |
Fmoc-Leu-OH | 92.0 | Fmoc-Trp(Boc)-OH | 80.3 |
Fmoc-Ile-OH | 92.3 | Fmoc-Asp(otBu)-OH | 84.2 |
Fmoc-Met-OH | 90.5 | Fmoc-Tyr(tBu)-OH | 82.1 |
Fmoc-Phe-OH | 88.7 | Fmoc-Glu(otBu)-OH | 81.9 |
Fmoc-Ala-OH | 94.0 | Fmoc-Cys(Trt)-OH | 78.5 |
Fmoc-Gly-OH | 95.3 | Fmoc-Gln(Trt)-OH | 75.3 |
Fmoc-Arg(Pbf)-OH | 65.0 | Fmoc-His(Trt)-OH | 70.2 |
Fmoc-Lys(Boc)-OH | 80.3 | Fmoc-Ser(tBu)-OH | 86.2 |
Table 2 Connection rate of modified resin to 20 kinds of amino acids
Amino acid | Connection rate(%) | Amino acid | Connection rate(%) |
---|---|---|---|
Fmoc-Val-OH | 93.2 | Fmoc-Thr(tBu)-OH | 84.9 |
Fmoc-pro-OH | 89.1 | Fmoc-Asn(Trt)-OH | 77.0 |
Fmoc-Leu-OH | 92.0 | Fmoc-Trp(Boc)-OH | 80.3 |
Fmoc-Ile-OH | 92.3 | Fmoc-Asp(otBu)-OH | 84.2 |
Fmoc-Met-OH | 90.5 | Fmoc-Tyr(tBu)-OH | 82.1 |
Fmoc-Phe-OH | 88.7 | Fmoc-Glu(otBu)-OH | 81.9 |
Fmoc-Ala-OH | 94.0 | Fmoc-Cys(Trt)-OH | 78.5 |
Fmoc-Gly-OH | 95.3 | Fmoc-Gln(Trt)-OH | 75.3 |
Fmoc-Arg(Pbf)-OH | 65.0 | Fmoc-His(Trt)-OH | 70.2 |
Fmoc-Lys(Boc)-OH | 80.3 | Fmoc-Ser(tBu)-OH | 86.2 |
Substitution degree/(mmol·g-1) | Yield(%) | Reaction time/h | Yield(%) |
---|---|---|---|
1.06 | 65.6 | 2 | 65.0 |
0.84 | 70.8 | 3 | 72.1 |
0.43 | 72.3 | 4 | 71.4 |
0.22 | 72.0 | 5 | 71.8 |
Table 3 Effects of resin substitution degree and reaction time on connection rate
Substitution degree/(mmol·g-1) | Yield(%) | Reaction time/h | Yield(%) |
---|---|---|---|
1.06 | 65.6 | 2 | 65.0 |
0.84 | 70.8 | 3 | 72.1 |
0.43 | 72.3 | 4 | 71.4 |
0.22 | 72.0 | 5 | 71.8 |
[1] | Merrifield R. B., J. Am. Chem. Soc., 1963, 85(14), 2149—2154 |
[2] | Nan Y. P., Chemistry & Bioengineering, 2005, 22(6), 34—36 |
(南亚萍. 化学与生物工程, 2005, 22(6), 34—36) | |
[3] | Tang H. K., Studies on Solid-Phase Synthesis, Purification and Preparation of Peptide JFT, Northwest University, Xi’an, 2007 |
(唐宏琨. 减肥多肽JFT的固相合成及纯化制备工艺研究. 西安: 西北大学, 2007) | |
[4] | Yang F. L., Li H. S., Wang J. L., Shanghai Medical & Pharmaceutical Journal, 2010, 31(9), 414—416 |
(燕方龙, 李洪森, 王金龙. 上海医药, 2010, 31(9), 414—416) | |
[5] | Han X., Wang D. X., Acta Pharmaceutica Sinica, 2007, 42(2), 111—117 |
(韩香, 王德心. 药学学报, 2007, 42(2), 111—117) | |
[6] | Huang B., Henan Chemical Industry, 2013, 30(1), 28—30 |
(黄蓓. 河南化工, 2013, 30(1), 28—30) | |
[7] | Behrendt R., White P., Offer J., J. Pept. Sci., 2016, 22(1), 4—5 |
[8] | Wang W. G., Chen W. H., Wen F., Journal of Nanjing University of Technology, 2007, 29(1), 12—15 |
(卫国, 陈伟华, 闻峰. 南京工业大学学报, 2007, 29(1), 12—15) | |
[9] | Chen Y. L., Chemical Synthetic Research on Peptide Segments Ligation, Peptide Derivatives and Conjugate of Modifer-peptidederivative, Shandong University, Jinan, 2009 |
(陈艳丽. 多肽片段连接、 衍生物及偶合物的化学合成研究, 济南: 山东大学, 2009) | |
[10] | Fu Y. W., Wu L., Chemical Industry and Engineering, 2010, 27(4), 92—97 |
(符友伟, 吴蕾. 化学工业与工程, 2010, 27(4), 92—97) | |
[11] | Góngora B. M., Tulla P. J., ACS Combination Science, 2013, 15(5), 217—228 |
[12] | Subirós F. R., Faham A., Albericio F., Biopolymers, 2012, 98(2), 89—97 |
[13] | Ieronymaki M., Androutsou M., Pantelia A., Biopolymers, 2015, 104(5), 506—514 |
[14] | Han Y. B., Li Y., Yang G. Q., Progress in Chemistry, 2004, 16(2), 142—148 |
(韩永滨, 李嫕, 杨国强. 化学进展, 2004, 16(2), 142—148) | |
[15] | Albericio F., Barany G., Tetrahedron Letters, 1991, 32(8), 1015—1018 |
[16] | Wang D.X., Solid-Phase Organic Synthesis: Principle and Application Guide, Chemical Industry Press, Beijing, 2004, 543 |
(王德心. 固相有机合成——原理及应用指南, 北京: 化学工业出版社, 2004, 543) | |
[17] | Lou S. J., Xiang H., Huang H., Ion Exchange and Adsorption, 1999, 15(1), 15—22 |
(娄素君, 向新, 黄海. 离子交换与吸附, 1999, 15(1), 15—22) | |
[18] | Wu N., Study on the Handle of Hydroquinones for Peptide Solid Phase Synthesis, The Chemical Defence Collage, Beijing, 2010 |
(吴宁. 用于肽类固相合成的羟基酸酯类把手的研究, 北京: 防化学院, 2010) | |
[19] | Zong L., Dong J. J., Chen J., Chem. J. Chinese Universities, 2016, 37(7), 110—116 |
(宗良, 董俊军, 陈静. 高等学校化学学报, 2016, 37(7), 110—116) | |
[20] | Wang W. G., Chen W. H., Wen F., Journal of Nanjing Tech University, 2007, 29(1), 12—15 |
(王卫国, 陈伟华, 闻峰. 南京工业大学学报, 2007, 29(1), 12—15) |
[1] | CAO Shujie, LI Hongjun, GUAN Wenli, REN Mengtian, ZHOU Chuanzheng. Progress on the Stereocontrolled Synthesis of Phosphorothioate Oligonucleotides [J]. Chem. J. Chinese Universities, 2022, 43(Album-4): 20220304. |
[2] | CHANG Liying, LING Xinyu, CHEN Heqi, WANG Xue, LIU Tao. Application of Gene Editing in Mitochondrial Diseases [J]. Chem. J. Chinese Universities, 2022, 43(Album-4): 20220363. |
[3] | LIU Wenting, LIU Liuyi, ZHU Bochen, MAO Zongwan. Progress on the Recognition, Complex Structure and Intracellular Detection of Nucleic Acid G-quadruplex [J]. Chem. J. Chinese Universities, 0, (): 20220419. |
[4] | ZHANG Kaisong, WANG Shaoru, ZHANG Yutong, TIAN Tian. Study of Epigenetic Modifications of Nucleic Acids Based on Supramolecular Chemistry [J]. Chem. J. Chinese Universities, 0, (): 20220335. |
[5] | ZHAO Zhuo, WANG Xueqiang. Investigations upon the Bioconjugation-based Construction Technologies and Applications of Aptamer-drug Conjugates [J]. Chem. J. Chinese Universities, 2021, 42(11): 3367. |
[6] | LI Shijie,YANG Yang,CUI Yingying,SU Xianbin. High Efficient and Green Approach to the Synthesis of Leuprolide in Continuous-flow Microreactor† [J]. Chem. J. Chinese Universities, 2020, 41(7): 1559. |
[7] | LIU Bingtong, ZHUANG Yongliang. Structural Characterization of Peptide Calcium Chelate VGLPNSR-Ca and Its Calcium Absorption Ability in Caco-2 Cell Monolayer [J]. Chem. J. Chinese Universities, 2019, 40(8): 1643. |
[8] | SHI Mai,JIANG Rui,CUI Xinxia,ZHANG Xin,SHEN Shigang,DING Liang,PAN Xuefeng. Preparation, Structure and Pharmaceutical Analysis of Protamine-siRNA Complexes† [J]. Chem. J. Chinese Universities, 2019, 40(6): 1164. |
[9] | ZHU Jingxuan,YU Zhengfei,LIU Ye,ZHAN Dongling,HAN Jiarui,TIAN Xiaopian,HAN Weiwei. Exploration of Increasing the Non-specificity Substrates Activity for the Phosphotriesterase-like Lactonase Using Molecular Dynamics Simulations† [J]. Chem. J. Chinese Universities, 2019, 40(1): 138. |
[10] | LI Cheng,SONG Jixue,LIU Tingting,LI Yan,LIU Bingnan,WANG Liang,XIAO Shan,LI Lin,GENG Xuhui,WANG Jihui. Detection of Egg White Lysozyme Oligomers Based on Fluorescence Lifetime of ThT† [J]. Chem. J. Chinese Universities, 2019, 40(1): 90. |
[11] | FAN Jiahui,BIAN Yanan,SU Xianbin. Synthesis of Liraglutide Through Threonine Ligation† [J]. Chem. J. Chinese Universities, 2018, 39(12): 2679. |
[12] | ZHAO Wencai, HAN Lili, PENG Yingjun, WANG Xiaojing, LIU Shengyu, LI Pengfei, HUANG Yibing, CHEN Yuxin. Effect of Basic Amino Acids on the Biological Activity of Helical Antimicrobial Peptide† [J]. Chem. J. Chinese Universities, 2018, 39(4): 681. |
[13] | LIU Fei, XIE Qing, LIU Teli, XU Xiaoxia, GUO Xiaoyi, LI Nan, ZHU Hua, YANG Zhi. Radio-synthesis, Quality Control and Micro-PET Imaging of 64Cu-DOTA-TATE† [J]. Chem. J. Chinese Universities, 2018, 39(4): 695. |
[14] | GAO Chaohui, LI Haili, WANG Lei, QIU Zhanglei, MU Jianshuai, LI Lianzhi. Interaction of Neuroglobin Mutant H64V with Azide Anion† [J]. Chem. J. Chinese Universities, 2018, 39(3): 476. |
[15] | CAO Yuhui, ZHANG Juanjuan, WANG Zaiyang, ZHAO Yuanhui. Separation and Identification of Oyster Peptide Modified by Plastein Reaction and Characterization of Peptide-zinc Complexes† [J]. Chem. J. Chinese Universities, 2018, 39(3): 470. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||