scholarly journals Optimal Method for Disulfide Bond Closure in the Synthesis of Atosiban—Antagonist of Oxytocin Receptors

2021 ◽  
Vol 47 (6) ◽  
pp. 1241-1248
Author(s):  
D. V. Avdeev ◽  
M. V. Ovchinnikov ◽  
Y. S. Dudkina ◽  
A. S. Molokoedov ◽  
A. A. Azmuko ◽  
...  

Abstract This work is devoted to the large-scale solid-phase synthesis (SPS) of Atosiban, Mpa1-D-Tyr(OEt)-Ile-Thr-Asn-Cys6-Pro-Orn-Gly-NH2 cyclic 1,6 disulfide, the only clinically used oxytocin receptor antagonist. The conditions have been selected for the closure of the disulfide bond (S–S) in the Atosiban molecule both in the solution and solid phase with the minimal formation of by-products. A comparative assessment of the formation of the S–S bond was carried out under various conditions. The formation of by-products during the closure of the disulfide bond has been studied both in solution and on the polymer support. The developed technique allows for the synthesis of Atosiban on an enlarged scale (10–20 mmol) involving the cyclization of a protected intermediate with the formation of the S–S bond during solid-phase synthesis with the minimal formation of by-products.

2013 ◽  
Vol 125 (36) ◽  
pp. 9737-9741 ◽  
Author(s):  
Hong-Kui Cui ◽  
Ye Guo ◽  
Yao He ◽  
Feng-Liang Wang ◽  
Hao-Nan Chang ◽  
...  

Tetrahedron ◽  
1994 ◽  
Vol 50 (8) ◽  
pp. 2617-2622 ◽  
Author(s):  
F.Xavier Montserrat ◽  
Anna Grandas ◽  
Ramon Eritja ◽  
Enrique Pedroso

2017 ◽  
Vol 58 (17) ◽  
pp. 1677-1680 ◽  
Author(s):  
Yang Xu ◽  
Tao Wang ◽  
Chao-Jian Guan ◽  
Yi-Ming Li ◽  
Lei Liu ◽  
...  

Small ◽  
2011 ◽  
Vol 7 (7) ◽  
pp. 957-964 ◽  
Author(s):  
Sanjay K. Apte ◽  
Sunil N. Garaje ◽  
Gurudas P. Mane ◽  
Ajayan Vinu ◽  
Sonali D. Naik ◽  
...  

2019 ◽  
Vol 60 (17) ◽  
pp. 1197-1201 ◽  
Author(s):  
Shuai-Shuai Sun ◽  
Junyou Chen ◽  
Rui Zhao ◽  
Donald Bierer ◽  
Jun Wang ◽  
...  

2020 ◽  
Vol 44 (23) ◽  
pp. 9634-9646 ◽  
Author(s):  
Sonali D. Naik ◽  
Sanjay K. Apte ◽  
Sunil N. Garaje ◽  
Yogesh A. Sethi ◽  
Manish D. Shinde ◽  
...  

Nanostructured CdIn2S4 and ZnIn2S4 with unique morphologies can be synthesized using this method which is simple and easy to operate.


2013 ◽  
Vol 24 (10) ◽  
pp. 873-876 ◽  
Author(s):  
Xiao-Feng Wang ◽  
Xian-Tao Yang ◽  
Yue Chen ◽  
Yang Liu ◽  
Lang Zou ◽  
...  

2013 ◽  
Vol 52 (36) ◽  
pp. 9558-9562 ◽  
Author(s):  
Hong-Kui Cui ◽  
Ye Guo ◽  
Yao He ◽  
Feng-Liang Wang ◽  
Hao-Nan Chang ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document