Diaminodiacid-Based Solid-Phase Synthesis of Peptide Disulfide Bond Mimics

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

Dmab/ivDde protected diaminodiacids for solid-phase synthesis of peptide disulfide-bond mimics

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

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 ◽  
...  
Keyword(s):  
Disulfide Bond ◽  
Large Scale ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Comparative Assessment ◽  
Polymer Support ◽  
Optimal Method ◽  
Phase Synthesis ◽  
Oxytocin Receptors ◽  
By Products

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.

Efficient synthesis of a side-chain extended diaminodiacid for solid-phase synthesis of peptide disulfide bond mimics

2019 ◽  
Vol 60 (17) ◽  
pp. 1197-1201 ◽  
Author(s):  
Shuai-Shuai Sun ◽  
Junyou Chen ◽  
Rui Zhao ◽  
Donald Bierer ◽  
Jun Wang ◽  
...  
Keyword(s):  
Disulfide Bond ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Chain ◽  
Efficient Synthesis ◽  
Phase Synthesis

Solid phase synthesis of peptide–siRNA conjugates containing disulfide bond unit

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

Diaminodiacid-Based Solid-Phase Synthesis of Peptide Disulfide Bond Mimics

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

Chemical Synthesis of Six‐Atom Thioether Bridged Diaminodiacid for Solid‐Phase Synthesis of Peptide Disulfide Bond Mimics

2020 ◽  
Vol 5 (4) ◽  
pp. 1359-1363 ◽  
Author(s):  
Junyou Chen ◽  
Shuaishuai Sun ◽  
Rui Zhao ◽  
Chen‐Peng Xi ◽  
Wenjie Qiu ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Disulfide Bond ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals Amino Acids and Peptides. XXVII. Solid Phase Synthesis of Fibrinogen-Related Peptides with Disulfide Bond Formed on Solid Support.

1996 ◽  
Vol 44 (5) ◽  
pp. 1107-1110 ◽  
Author(s):  
Masa KAKIUCHI ◽  
Yasuhiro IZUNO ◽  
Mitsuko MAEDA ◽  
Kaori UEDA ◽  
Kazuko FUJIWARA ◽  
...  
Keyword(s):  
Amino Acids ◽  
Disulfide Bond ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Phase Synthesis

scholarly journals Preparation of canine relaxin by Fmoc-solid phase synthesis and regioselective disulfide bond formation within the A- and B-chains

2013 ◽  
Vol 1 (1) ◽  
pp. 4 ◽  
Author(s):  
Feng Lin ◽  
Julien Tailhades ◽  
Linda J Chan ◽  
Ross A.D Bathgate ◽  
Mohammed Akhter Hossain ◽  
...  
Keyword(s):  
Disulfide Bond ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Bond Formation ◽  
Disulfide Bond Formation ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis
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