Synthesis of cyclic peptide disulfide–PHPMA conjugates via sequential active ester aminolysis and CuAAC coupling

2016 ◽  
Vol 7 (4) ◽  
pp. 970-978 ◽  
Author(s):  
Kemal Arda Günay ◽  
Harm-Anton Klok
Keyword(s):  
Cyclic Peptide ◽  
Protecting Groups ◽  
Polymer Conjugates ◽  
Synthetic Strategy ◽  
Active Ester ◽  
Ester Aminolysis

A synthetic strategy for the preparation of cyclic peptide disulfide–polymer conjugates that does not require peptide protecting groups is reported.

Hierarchical Assembly of Branched Supramolecular Polymers from (Cyclic Peptide)–Polymer Conjugates

2014 ◽  
Vol 15 (11) ◽  
pp. 4002-4011 ◽  
Author(s):  
Ming Liang Koh ◽  
Katrina A. Jolliffe ◽  
Sébastien Perrier
Keyword(s):  
Cyclic Peptide ◽  
Supramolecular Polymers ◽  
Hierarchical Assembly ◽  
Polymer Conjugates

scholarly journals Synthesis of the spiroketal core of integramycin

2013 ◽  
Vol 9 ◽  
pp. 2446-2450
Author(s):  
Evgeny V Prusov
Keyword(s):  
Integrase Inhibitor ◽  
Protecting Groups ◽  
Hiv Integrase ◽  
Acylation Reaction ◽  
Synthetic Strategy

A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.

The AA* + B*B2 approach A simple and convenient synthetic strategy towards hyperbranched polyurea-urethanes

e-Polymers ◽  
2003 ◽  
Vol 3 (1) ◽  
Author(s):  
Bernd Bruchmann ◽  
Wolfgang Schrepp
Keyword(s):  
Functional Groups ◽  
Raw Materials ◽  
Protecting Groups ◽  
Isophorone Diisocyanate ◽  
Step Process ◽  
Synthetic Strategy ◽  
One Step

Abstract Synthesizing hyperbranched polyurethanes in a one step process using commercially available raw materials: these were the primary conditions for this work. By taking advantage of intramolecular reactivity differences of isocyanate groups in diisocyanates in combination with reactivity differences of OH and NH groups in alkanolamines, it is possible to generate in situ AB2 molecules by controlling reactions of specific functional groups towards each other. This AA* + B*B2 approach works without protecting groups and opens up a simple and versatile strategy towards hyperbranched aromatic as well as aliphatic polyureaurethanes. Preferential diisocyanates for this synthesis were 2,4-toluylene diisocyanate and isophorone diisocyanate, whereas diethanolamine and diisopropanolamine were used as isocyanate-reactive counterparts.

Synthesis of a branched cyclic peptide using a strategy employing Fmoc chemistry and two additional orthogonal protecting groups

1993 ◽  
Vol 34 (29) ◽  
pp. 4709-4712 ◽  
Author(s):  
G.B. Bloomberg ◽  
D. Askin ◽  
A.R. Gargaro ◽  
M.J.A. Tanner
Keyword(s):  
Cyclic Peptide ◽  
Protecting Groups ◽  
Fmoc Chemistry

scholarly journals Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

2020 ◽  
Vol 76 (10) ◽  
pp. 1653-1656
Author(s):  
Adam Wood ◽  
Paul V. Bernhardt ◽  
Ian van Altena ◽  
Michela I. Simone
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Biological Activities ◽  
Membered Ring ◽  
Protecting Groups ◽  
Hydroxyl Groups ◽  
Synthetic Strategy ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Cross Links

Short syntheses to high Fsp 3 index natural-product analogues such as iminosugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An isopropylidene group was employed towards the synthesis of seven-membered ring iminosugars and the title compound, C9H15N3O5, was crystallized as an intermediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O—H...(O,O) and O—H...N hydrogen-bonding interactions, which generate chains of molecules propagating parallel to the a-axis direction. There is a notable non-classical C—H...O hydrogen bond, which cross-links the [100] chains into (001) sheets.

scholarly journals HPMA-Based Polymer Conjugates for Repurposed Drug Mebendazole and Other Imidazole-Based Therapeutics

Polymers ◽  
2021 ◽  
Vol 13 (15) ◽  
pp. 2530
Author(s):  
Martin Studenovský ◽  
Anna Rumlerová ◽  
Libor Kostka ◽  
Tomáš Etrych
Keyword(s):  
Chemical Properties ◽  
Drug Repurposing ◽  
Water Soluble ◽  
Biologically Active ◽  
Lysosomal Hydrolases ◽  
Polymer Carrier ◽  
Design Synthesis ◽  
Polymer Conjugates ◽  
Synthetic Strategy ◽  
Physico Chemical

Recently, the antitumor potential of benzimidazole anthelmintics, such as mebendazole and its analogues, have been reported to have minimal side effects, in addition to their well-known anti-parasitic abilities. However, their administration is strongly limited owing to their extremely poor solubility, which highly depletes their overall bioavailability. This study describes the design, synthesis, and physico-chemical properties of polymer-mebendazole nanomedicines for drug repurposing in cancer therapy. The conjugation of mebendazole to water-soluble and biocompatible polymer carrier was carried out via biodegradable bond, relying on the hydrolytic action of lysosomal hydrolases for mebendazole release inside the tumor cells. Five low-molecular-weight mebendazole derivatives, differing in their inner structure, and two polymer conjugates differing in their linker structure, were synthesized. The overall synthetic strategy was designed to enable the modification and polymer conjugation of most benzimidazole-based anthelmintics, such as albendazole, fenbendazole or albendazole, besides the mebendazole. Furthermore, the described methodology may be suitable for conjugation of other biologically active compounds with a heterocyclic N-H group in their molecules.

Facile one-pot synthesis of cyclic peptide-conjugated photosensitisers for targeted photodynamic therapy

2020 ◽  
Vol 56 (80) ◽  
pp. 11941-11944
Author(s):  
Jacky C. H. Chu ◽  
Caixia Yang ◽  
Wing-Ping Fong ◽  
Clarence T. T. Wong ◽  
Dennis K. P. Ng
Keyword(s):  
Photodynamic Therapy ◽  
Cyclic Peptide ◽  
One Pot ◽  
One Pot Synthesis ◽  
Synthetic Strategy ◽  
Targeted Photodynamic Therapy

A facile synthetic strategy for in situ cyclisation of peptides and conjugation with functional boron dipyrromethenes (BODIPYs) using a bifunctional linker is reported.

scholarly journals Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

2020 ◽  
Vol 16 ◽  
pp. 106-110 ◽  
Author(s):  
Tapasi Manna ◽  
Arin Gucchait ◽  
Anup Kumar Misra
Keyword(s):  
Cell Wall ◽  
Perchloric Acid ◽  
Good Yield ◽  
Protecting Groups ◽  
O Antigen ◽  
Synthetic Strategy ◽  
Convenient Synthesis ◽  
Selection Of ◽  
Glycosyl Donors

A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO4/SiO2) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates.

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