Combinatorial Synthesis of Exohedrally Modified Fullerene Derivatives

2003 ◽  
Vol 17 (08n09) ◽  
pp. 1910-1915 ◽  
Author(s):  
Yasuhiko Kawamura ◽  
Yasuyuki Akai ◽  
Masao Tsukayama
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Combinatorial Synthesis ◽  
Environmentally Benign ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Compound Library ◽  
Phase Synthesis ◽  
Fullerene Derivatives ◽  
Wide Range

Fulleropyrrolidines have been very welcomed in a community of a fullerene science. But sometimes the synthesis ends up with disappointing yields of the products. In order to overcome the problem and to explore more environmentally benign method for synthesizing fullerene derivatives having various attachment on the surface of the fullerenes, a solid-phase synthesis is examined. We found that the dipolar cycloaddition of an azomethine ylide, i.e., 2-phenyl-N-benzylideneglycine methyl ester, supported on a Wang resin, proceeded feasibly with C 60 and the objective fulleropyrrolidines were afforded in good yields (>75%). The method is expected to be utilized with wide range of application and it is therefore able to provide a compound library of modified fullerenes which is hard to obtain by other methods employed so far.

Solid Phase Synthesis of Novel Fullerene Nucleotides Conjugates

2011 ◽  
Vol 266 ◽  
pp. 200-203
Author(s):  
Jing Zhang ◽  
Ya Dong Zhang
Keyword(s):  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Azomethine Ylide ◽  
Hydroxyl Group ◽  
Spectrometric Analysis ◽  
Phase Synthesis ◽  
Chemical Structures ◽  
Controlled Pore Glass

N-substituted 3, 4-fullero pyrrolidine was synthesized according to 1, 3-dipolar cycloaddition of the azomethine ylide. Aspartic acid with protected α-amino and α-carboxyl groups was reacted with the activated hydroxyl group of N-substituted 3, 4-fullero pyrrolidine. The products were deprotected, affording the monofullerene aspartic acid (mFas). The conjugate FasT was synthesized by reaction of mFas containing protected amino group with the thymidylic acid derivatived controlled pore glass (CPG) using solid phase synthesis. All of the above fullerene derivatives were characterized by UV–vis, 1H NMR, IR and MS spectrometric analysis, giving the correct spectra with regard to their chemical structure. The chemical structures of fullerene nucleotides conjugate FasT is different from previous reports and may have novel biological properties. Moreover, they are more suitable for applications in biomedical research due to their solubilization in THF and DMSO. They have a potential to be used as monomer for the automatic synthesis. It allows further conjugation with specific biomolecules including amino acids, peptides, nucleotides and nucleic acids. A novel method has been developed to synthesize fullerene nucleotides conjugate. Their unique chemical structures make them very interesting for their potential use in medicine and biology.

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

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.

Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support

2001 ◽  
Vol 66 (7) ◽  
pp. 1078-1106 ◽  
Author(s):  
Viktor Krchňák ◽  
Jennifer Smith ◽  
Josef Vágner
Keyword(s):  
Drug Discovery ◽  
Hydrogen Atom ◽  
Heterocyclic Compounds ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Combinatorial Synthesis ◽  
Target Compound ◽  
Phase Synthesis ◽  
Acidic Reagent

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.

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