Recent Advances in the Chemical Synthesis of Marine Acidic Carbohydrates

2020 ◽  
Vol 24 ◽  
Author(s):  
Xinru Li ◽  
Depeng Wang ◽  
Ping Zhang ◽  
Guangli Yu ◽  
Chao Cai

: The ocean supplies abundant active compounds, including small organic molecules, proteins, lipids, and carbohydrates, with diverse biological functions. The high-value transformation of marine carbohydrates primarily refers to their pharmaceutical, food, and cosmetic applications. However, it is still a big challenge to obtain these marine carbohydrates in well-defined structures. Synthesis is a powerful approach to access marine oligosaccharides, polysaccharide derivatives, and glycomimetics. In this review, we focus on the chemical synthesis of marine acidic carbohydrates with acidic ester groups or uronic acid building blocks including alginate, glycosaminoglycans. Regioselective sulfation using a chemical approach is also highlighted in the synthesis of marine oligosaccharides, as well as the multivalent glycodendrimers and glycopolymers for achieving specific functions. This review summarizes recent advances in the synthesis of marine acidic carbohydrates, as well as their preliminary structure activity relationship (SAR) studies, which establishes a foundation for the development of novel marine carbohydrate-based drugs and functional reagents.

2018 ◽  
Vol 47 (15) ◽  
pp. 5554-5573 ◽  
Author(s):  
Jing Mu ◽  
Jing Lin ◽  
Peng Huang ◽  
Xiaoyuan Chen

This review summarizes the recent progress of endogenous enzyme-responsive nanomaterials based on different building blocks such as polymers, liposomes, small organic molecules, or inorganic/organic hybrid materials for theranostics.


ChemInform ◽  
2014 ◽  
Vol 45 (19) ◽  
pp. no-no
Author(s):  
Antonio Rescifina ◽  
Chiara Zagni ◽  
Maria Giulia Varrica ◽  
Venerando Pistara ◽  
Antonino Corsaro

2012 ◽  
Vol 8 ◽  
pp. 930-940 ◽  
Author(s):  
Hiroki Oguri ◽  
Haruki Mizoguchi ◽  
Hideaki Oikawa ◽  
Aki Ishiyama ◽  
Masato Iwatsuki ◽  
...  

By emulating the universal biosynthetic strategy, which employs modular assembly and divergent cyclizations, we have developed a four-step synthetic process to yield a collection of natural-product-inspired scaffolds. Modular assembly of building blocks onto a piperidine-based manifold6, having a carboxylic acid group, was achieved through Ugi condensation,N-acetoacetylation and diazotransfer, leading to cyclization precursors. The rhodium-catalyzed tandem cyclization and divergent cycloaddition gave rise to tetracyclic and hexacyclic scaffolds by the appropriate choice of dipolarophiles installed at modules 3 and 4. A different piperidine-based manifold15bearing an amino group was successfully applied to demonstrate the flexibility and scope of the unified four-step process for the generation of structural diversity in the fused scaffolds. Evaluation of in vitro antitrypanosomal activities of the collections and preliminary structure–activity relationship (SAR) studies were also undertaken.


2013 ◽  
Vol 51 (8) ◽  
pp. 447-453 ◽  
Author(s):  
Bertrand Plainchont ◽  
Vicente de Paulo Emerenciano ◽  
Jean-Marc Nuzillard

Author(s):  
Qiuyan Guo ◽  
Enshe Jiang

: Podophyllotoxins including epipodophyllotoxin derivatives can act on a diverse array of drug targets in cancer cells, and thus possess potential activity against various forms of cancer cell lines including drug-resistant forms. Moreover, several podophyllotoxin derivatives which are represented by etoposide and teniposide have already been approved for the cancer therapy, demonstrating podophyllotoxin moiety is a useful pharmacophore for the discovery of novel anticancer agents. This review reports the recent advances in exploitation of podophyllotoxin derivatives to fight against multidrug-resistant cancer cells. The mechanism of action and structure-activity relationship (SAR) studies are also highlighted.


2014 ◽  
Vol 74 ◽  
pp. 95-115 ◽  
Author(s):  
Antonio Rescifina ◽  
Chiara Zagni ◽  
Maria Giulia Varrica ◽  
Venerando Pistarà ◽  
Antonino Corsaro

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Helge Mißbach ◽  
Jan-Peter Duda ◽  
Alfons M. van den Kerkhof ◽  
Volker Lüders ◽  
Andreas Pack ◽  
...  

AbstractIt is widely hypothesised that primeval life utilised small organic molecules as sources of carbon and energy. However, the presence of such primordial ingredients in early Earth habitats has not yet been demonstrated. Here we report the existence of indigenous organic molecules and gases in primary fluid inclusions in c. 3.5-billion-year-old barites (Dresser Formation, Pilbara Craton, Western Australia). The compounds identified (e.g., H2S, COS, CS2, CH4, acetic acid, organic (poly-)sulfanes, thiols) may have formed important substrates for purported ancestral sulfur and methanogenic metabolisms. They also include stable building blocks of methyl thioacetate (methanethiol, acetic acid) – a putative key agent in primordial energy metabolism and thus the emergence of life. Delivered by hydrothermal fluids, some of these compounds may have fuelled microbial communities associated with the barite deposits. Our findings demonstrate that early Archaean hydrothermal fluids contained essential primordial ingredients that provided fertile substrates for earliest life on our planet.


Author(s):  
Joshua Horton ◽  
Alice Allen ◽  
Leela Dodda ◽  
Daniel Cole

<div><div><div><p>Modern molecular mechanics force fields are widely used for modelling the dynamics and interactions of small organic molecules using libraries of transferable force field parameters. For molecules outside the training set, parameters may be missing or inaccurate, and in these cases, it may be preferable to derive molecule-specific parameters. Here we present an intuitive parameter derivation toolkit, QUBEKit (QUantum mechanical BEspoke Kit), which enables the automated generation of system-specific small molecule force field parameters directly from quantum mechanics. QUBEKit is written in python and combines the latest QM parameter derivation methodologies with a novel method for deriving the positions and charges of off-center virtual sites. As a proof of concept, we have re-derived a complete set of parameters for 109 small organic molecules, and assessed the accuracy by comparing computed liquid properties with experiment. QUBEKit gives highly competitive results when compared to standard transferable force fields, with mean unsigned errors of 0.024 g/cm3, 0.79 kcal/mol and 1.17 kcal/mol for the liquid density, heat of vaporization and free energy of hydration respectively. This indicates that the derived parameters are suitable for molecular modelling applications, including computer-aided drug design.</p></div></div></div>


Author(s):  
Joshua Horton ◽  
Alice Allen ◽  
Leela Dodda ◽  
Daniel Cole

<div><div><div><p>Modern molecular mechanics force fields are widely used for modelling the dynamics and interactions of small organic molecules using libraries of transferable force field parameters. For molecules outside the training set, parameters may be missing or inaccurate, and in these cases, it may be preferable to derive molecule-specific parameters. Here we present an intuitive parameter derivation toolkit, QUBEKit (QUantum mechanical BEspoke Kit), which enables the automated generation of system-specific small molecule force field parameters directly from quantum mechanics. QUBEKit is written in python and combines the latest QM parameter derivation methodologies with a novel method for deriving the positions and charges of off-center virtual sites. As a proof of concept, we have re-derived a complete set of parameters for 109 small organic molecules, and assessed the accuracy by comparing computed liquid properties with experiment. QUBEKit gives highly competitive results when compared to standard transferable force fields, with mean unsigned errors of 0.024 g/cm3, 0.79 kcal/mol and 1.17 kcal/mol for the liquid density, heat of vaporization and free energy of hydration respectively. This indicates that the derived parameters are suitable for molecular modelling applications, including computer-aided drug design.</p></div></div></div>


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