Macrolactonization Driven by Supramolecular Interactions

Author(s):  
guillaume force ◽  
david leboeuf

Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progresses made towards their synthesis, notably from <i>seco</i>-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe an alternative strategy relying on a speculated supramolecular template to enable a convenient access to macrolactones, macrodiolides and esters with a versatility that had not been reached with classic methods.

2020 ◽  
Author(s):  
guillaume force ◽  
david leboeuf

Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progresses made towards their synthesis, notably from <i>seco</i>-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe an alternative strategy relying on a speculated supramolecular template to enable a convenient access to macrolactones, macrodiolides and esters with a versatility that had not been reached with classic methods.


Polymers ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 624
Author(s):  
Cintya Dharmayanti ◽  
Todd A. Gillam ◽  
Manuela Klingler-Hoffmann ◽  
Hugo Albrecht ◽  
Anton Blencowe

Synthetic polypeptides and polymer-peptide hybrid materials have been successfully implemented in an array of biomedical applications owing to their biocompatibility, biodegradability and ability to mimic natural proteins. In addition, these materials have the capacity to form complex supramolecular structures, facilitate specific biological interactions, and incorporate a diverse selection of functional groups that can be used as the basis for further synthetic modification. Like conventional synthetic polymers, polypeptide-based materials can be designed to respond to external stimuli (e.g., light and temperature) or changes in the environmental conditions (e.g., redox reactions and pH). In particular, pH-responsive polypeptide-based systems represent an interesting avenue for the preparation of novel drug delivery systems that can exploit physiological or pathological pH variations within the body, such as those that arise in the extracellular tumour microenvironment, intracellularly within endosomes/lysosomes, or during tissue inflammation. Here, we review the significant progress made in advancing pH-responsive polypeptides and polymer-peptide hybrid materials during the last five years, with a particular emphasis on the manipulation of ionisable functional groups, pH-labile linkages, pH-sensitive changes to secondary structure, and supramolecular interactions.


2021 ◽  
Author(s):  
Mehboobali Pannipara ◽  
Abdullah G Al-Sehemi

Abstract Carboxylic acid supramolecular synthon exhibited dimer or catemer motifs in the crystal lattice depend on the substituent and other functional groups present in the structure. In general, presence of other competing functional groups produced catemer motifs whereas unsubstituted acids showed dimer. In this manuscript, we have synthesized a new aryl ether amine-based Schiff base with carboxylic acid functionality ( 1 ) and demonstrated polymorphic structure via catemer ( 1a ) and dimer ( 1b ) motifs in the solid state. In both the structure, carboxylic acid group adopted different orientation in the crystal lattice. The different H-bonding lead to modulation of optical properties that was further supported highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) calculation. Further the stability calculation indicates that catemer structure was more stable by 8.54 kcal/mole relative to dimer motifs. In contrast, naphthyl group attached carboxylic acid structure did not show neither dimer nor catemer motifs in the crystal lattice as compared to diethylaminophenyl group, which confirm the presence of other substituent or competing functional groups strongly influence on the motifs of supramolecular interactions.


2020 ◽  
Vol 14 (2) ◽  
pp. 134-153 ◽  
Author(s):  
A. S. Herc ◽  
M. Wlodarska ◽  
M. Nowacka ◽  
J. Bojda ◽  
W. Szymanski ◽  
...  

1971 ◽  
Vol 25 (1) ◽  
pp. 76-79 ◽  
Author(s):  
J. P. Luongo

The highly advanced polymerization techniques developed in the natural and synthetic resin industries have created a strong demand, not only for general identification of polymeric substances, but for the characterization of the newer stereoregular polymers. Although the gross ir spectral features of a particular polymer are mostly attributable to its functional groups, there are often many small but significant spectral differences which are associated with different structural arrangements that can exist within the polymer. Thus, in a number of cases the subtle spectral differences can be correlated with molecular configurations and used as evidence for various structures.


Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 954-958 ◽  
Author(s):  
Fu-Xue Chen ◽  
Pran Karmaker ◽  
Jiashen Qiu ◽  
Di Wu ◽  
Hongquan Yin

A novel and convenient oxidative radical cyclization of N-substituted N-arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K2S2O8 as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.


2008 ◽  
Vol 8 (9) ◽  
pp. 3420-3429 ◽  
Author(s):  
Andrzej Wierzbicki ◽  
Charles A. Knight ◽  
E. Alan Salter ◽  
Camden N. Henderson ◽  
Jeffry D. Madura

2022 ◽  
pp. 260-285
Author(s):  
Nidhi Yogeshbhai Patel ◽  
Shivani Maheshkumar Yagnik ◽  
Dhritiksha Mansukhbhai Baria ◽  
Vikram Hiren Raval

Extremophiles are at center stage of scientific interest owing to their peculiar properties in terms of physiology, ecology, biochemistry, and molecular genetics. The bio-active compounds from extremophiles involve various types of extremolytes. The functional applicability of extremophiles has been far-reaching. Looking to the global scenario medical, pharmaceutical and allied healthcare sectors have a persistent surge for a novel anticancer, antimicrobial, stable drug deliverables, nutraceuticals, fine chemicals, natural antioxidants, and bio-polymers compounds. Genetic engineering tools clubbed with -omics approach enhance and better the chances for applicability of the extremophilic metabolites in varied sectors of red and yellow biotechnology. The chapter provides an insight into the various types of bio-active molecules from extremophiles and their wide biotechnological applicability in the medical and pharmaceutical industry.


2015 ◽  
Vol 76 (10) ◽  
Author(s):  
Syarifah Nor Faizah Syed Abdul Rahman ◽  
Norazah Abd Rahman ◽  
Siti Shawalliah Idris ◽  
Noor Fitrah Abu Bakar ◽  
Roslan Mokhtar

Over recent years, there has been an explosive growth of interest in the development of novel gel-phase materials based on small molecules. It has been recognised that an effective gelator should possess functional groups that interact with each other via temporal associative forces. This process leads to the formation of supramolecular polymer-like structures, which then aggregated further hence, gelating the solvent. Supramolecular interactions between building blocks that enable gel formation include hydrogen bonds, interactions, solvatophobic effects and van der Waals forces.  


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