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

The possibility of synthesizing HTSC ceramics in the reaction chamber of a plasma-chemical reactor is shown. The method allows one to significantly reduce the process of solid-phase synthesis and obtain modified HTSC ceramics with a given content of non-superconducting additives that act as pinning centers.

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Postsynthetic On-Column 2′ Functionalization of RNA by Convenient Versatile Method

International Journal of Molecular Sciences ◽

10.3390/ijms21145127 ◽

2020 ◽

Vol 21 (14) ◽

pp. 5127

Author(s):

Olga A. Krasheninina ◽

Veniamin S. Fishman ◽

Alexander A. Lomzov ◽

Alexey V. Ustinov ◽

Alya G. Venyaminova

Keyword(s):

Chemical Synthesis ◽

Physicochemical Properties ◽

Functional Groups ◽

Convenient Method ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Protecting Groups ◽

Hydroxyl Group ◽

Phase Synthesis ◽

Wide Range

We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2′ position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2′-O-protecting groups, namely 2′-O-thiomorpholine-carbothioate (TC, as “permanent”) and 2′-O-tert-butyl(dimethyl)silyl (tBDMS, as “temporary”), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynthetic 2′ functionalization of the naked hydroxyl group. This convenient method to tailor RNA, utilizing the advantages of solid phase approaches, gives an opportunity to introduce site-specifically a wide range of linkers and functional groups. By this strategy, a series of RNAs containing diverse 2′ functionalities were synthesized and studied with respect to their physicochemical properties.

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

Tetrahedron Letters ◽

10.1016/j.tetlet.2017.03.024 ◽

2017 ◽

Vol 58 (17) ◽

pp. 1677-1680 ◽

Cited By ~ 9

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

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

Russian Journal of Bioorganic Chemistry ◽

10.1134/s1068162021060042 ◽

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.

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

Tetrahedron Letters ◽

10.1016/j.tetlet.2019.03.061 ◽

2019 ◽

Vol 60 (17) ◽

pp. 1197-1201 ◽

Cited By ~ 3

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

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

Chinese Chemical Letters ◽

10.1016/j.cclet.2013.06.010 ◽

2013 ◽

Vol 24 (10) ◽

pp. 873-876 ◽

Cited By ~ 1

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

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SOLID-PHASE SYNTHESIS: FROM REVOLUTION TO EVOLUTION

COSMOS ◽

10.1142/s0219607708000275 ◽

2008 ◽

Vol 04 (01) ◽

pp. 17-37 ◽

Cited By ~ 1

Author(s):

BRENDAN A. BURKETT

Keyword(s):

Chemical Synthesis ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Chemical Research ◽

Phase Synthesis ◽

The World ◽

The Face ◽

Over Time

Solid-phase synthesis is a technique of synthesizing compounds that was first reported by R. Bruce Merrifield in 1963. This revolutionary way of performing chemical synthesis has changed the face of synthesis — yet few people outside the halls of chemical research will ever hear about it. So, what is this technique and why is it useful? How has the technique of solid-phase synthesis changed the world? How has the solid-phase synthesis changed over time? This article aims to give a background of the area of solid-phase synthesis and answer these questions.

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