多肽酰肼法合成Nesiritide
收稿日期: 2014-01-24
修回日期: 2014-03-22
网络出版日期: 2014-04-02
基金资助
国家自然科学基金(Nos.21102083;21372058)资助项目.
Synthesis of Nesiritide via Ligation of Peptide Hydrazide
Received date: 2014-01-24
Revised date: 2014-03-22
Online published: 2014-04-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 201102083, 21372058).
Nesiritide是一类重要的多肽类血管扩张药物,在维持心血管和肾脏的体内平衡方面发挥着重要的作用. 目前,Nesiritide的合成主要是通过基因重组表达法获得,该方法操作较为复杂且存在一定的限制. 本研究运用多肽固相合成及酰肼连接策略,通过3片段连接高效合成了Nesiritide,为大批量工业化生产该类多肽药物打下基础.
关键词: 多肽酰肼连接; 自然化学连接; 多肽硫酯; Nesiritide
陈晨晨 , 李思践 , 陈轶群 , 许华建 , 李宜明 . 多肽酰肼法合成Nesiritide[J]. 有机化学, 2014 , 34(7) : 1452 -1457 . DOI: 10.6023/cjoc201401039
Nesiritide is an important class of peptide vasodilator. It plays a significant role in the maintenance homeostasis of cardiovascular and kidney. Nowadays, nesiritide is mainly obtained by biological methods including gene recombinant expression, which is relative time-consuming. In present work, the chemical synthesis of nesiritide was reported by using (solid-phase peptide synthesis) (SPPS) strategy combining with the ligation of peptide hydrazides with high yield and purity. Therefore, it was considered that the method presented here provided a convinced alternative for acquiring pharmaceutical peptide in a large scale.
[1] (a) Kent, S. B. H. Chem. Soc. Rev. 2009, 38, 338.
(b) Hemantha, H. P.; Narendra, N.; Sureshbabu, V. V. Tetrahedron 2012, 68, 9491.
[2] Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776.
[3] (a) Hojo, H.; Aimoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 111.
(b) Camarero, J. A.; Cotton, G. J.; Adeva, A.; Muir, T. W. J. Pept. Res. 1998, 51, 303.
(c) Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 10068.
(d) Varadi, G.; Togh, G. K.; Kele, Z.; Galgoczy, L.; Fizil, A.; Batta, G. Chem. Eur. J. 2013, 19, 12864.
[4] (a) Mende, F.; Seitz, O. Angew. Chem., Int. Ed. 2011, 50, 1232.
(b) Macmillan, D.; Adams, A.; Premdjee, B. Isr. J. Chem. 2011, 51, 855.
[5] (a) Botti, P.; Villain, M.; Manganiello, S.; Gaertner, H. Org. Lett. 2004, 6, 4861.
(b) Warren, J. D.; Miller, J. S.; Keding, S. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6576.
(c) Zheng, J. S.; Cui, H. K.; Fang, G. M.; Xi, W. X.; Liu, L. ChemBioChem 2010, 11, 511.
(d) Fang, G. M.; Cui, H. K.; Zheng, J. S.; Liu, L. ChemBioChem 2010, 11, 1061.
(e) Zheng, J. S.; Chang, H. N.; Shi, J.; Liu, L. Sci. China Chem. 2012, 55, 64.
[6] (a) Zheng, J. S.; Chang, H. N.; Wang, F. L.; Liu, L. J. Am. Chem. Soc. 2011, 133, 11080.
(b) Ollivier, N.; Behr, J. B.; El-Mahdi, O.; Blanpain, A.; Melnyk, O. Org. Lett. 2005, 7, 2647.
(c) Nagaike, F.; Onuma, Y.; Kanazawa, C.; Hojo, H.; Ueki, A.; Nakahara, Y.; Nakahara, Y. Org. Lett. 2006, 8, 4465.
(d) Ohta, Y.; Itoh, S.; Shigenaga, A.; Shintaku, S.; Fujii, N.; Otaka, A. Org. Lett. 2006, 8, 467.
(e) Kang, J.; Richardson, J. P.; Macmillan, D. Chem. Commun. 2009, 407.
(f) Ollivier, N.; Dheur, J.; Mhidia, R.; Blanpain, A.; Melnyk, O. Org. Lett. 2010, 12, 5238.
(g) Hou, W.; Zhang, X.; Li, F.; Liu, C. F. Org. Lett. 2011, 13, 386.
(h) Sharma, R.; Tam, J. P. Org. Lett. 2011, 13, 5176.
(i) Kawakami, T.; Sumida, M.; Nakamura, K.; Vorherr, T.; Aimoto, A. Tetrahedron Lett. 2005, 46, 8805.
[7] Kawakami, T.; Aimoto, S. Chem. Lett. 2007, 36, 76.
[8] Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369.
[9] Blanco-Canosa, J. B.; Dawson, P. E. Angew. Chem., Int. Ed. 2008, 47, 6851.
[10] (a) Fang, G. M.; Li, Y. M.; Shen, F.; Huang, Y. C.; Li, J. B.; Lin, Y.; Cui, H. K.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 7645.
(b) Zheng, J. S.; Tang, S.; Huang, Y. C.; Liu, L. Acc. Chem. Res., 2013, 46, 2475.
[11] (a) Fang, G. M.; Wang, J. X.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 10472.
(b) Li, Y. M.; Yang, M. Y.; Huang, Y. C.; Li, Y. T.; Chen, P. R.; Liu, L. ACS Chem. Biol. 2012, 7, 1015.
(c) Zheng, J. S.; Tang, S.; Qi, Y. K.; Wang, Z. P.; Liu, L. Nat. Protocols 2013, 8, 2483.
(d) Li, Y. M.; Li Y. T.; Pan, M.; Kong, X. Q.; Huang, Y. C.; Hong, Z. Y.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 2198.
(e) Zheng, J. S.; Yu, M.; Qi, Y. K.; Tang, S.; Shen, F.; Wang, Z. P.; Xiao, L.; Zhang, L. H.; Tian, C. L.; Liu, L. J. Am. Chem. Soc. 2014, 136, 3695.
(f) Tang, S.; Zheng, J. S.; Yang, K.; Liu, L. Acta Chim. Sinica 2012, 70, 1471.
(g) Pan, M.; He, Y.; Wen, M.; Wu, F. M.; Sun, D. M.; Li, S. J.; Zhang, L. H.; Li, Y. M.; Tian, C. L. Chem. Commun. 2014, 50, 5837.
(h) Huang, Y. C.; Chen, C. C.; Li, S. J.; Gao, S.; Shi, J.; Li, Y. M. Tetrahedron 2014, 70, 2951.
(i) Chen, Y. Q.; Chen, C. C.; He, Y.; Yu, M.; Xu, L.; Tian, C. L.; Guo, Q. X.; Shi, J.; Zhang, M.; Li, Y. M. Tetrahedron Lett. 2014, 55: 2883.
[12] Boerrigter, G.; Costello-Boerrigter, L. C.; Burnett, J. C. Jr. Heart Fail Clin. 2009, 5(4), 501.
[13] Mukoyama, M.; Nakao, K.; Hosoda, K.; Suga, S.; Saito, Y.; Ogawa, Y.; Shirakami, G.; Jougasaki, M.; Obata, K.; Yasue, H.; Kambayashi, Y.; Inouye, K.; Imura, H. J. Clin. Invest. 1991, 87, 1402.
[14] James, A. L.; Darren, K. M.; Mark, H. D. Lancet 2003, 362, 316.
[15] Laxmi, S. R.; Milind, P. N.; Dinesh, P.; Rakesh, S.; Aruna, G. K.; S. Uma; Priti, T.; Anjali, C.; Neelesh, S.; Radhika, S.; Sagar, Z. Biotechnol. Bioproc. Engl. 2011, 16, 688.
(b) Jeffrey, J. S. M. WO 8912069, 1989[Chem. Abstr. 1989, 114(17), 158509].
/
〈 |
|
〉 |