scholarly journals Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

2013 ◽  
Vol 9 ◽  
pp. 56-63 ◽  
Author(s):  
Daniel Fürniss ◽  
Timo Mack ◽  
Frank Hahn ◽  
Sidonie B L Vollrath ◽  
Katarzyna Koroniak ◽  
...  
Keyword(s):  
Nucleic Acids ◽  
Click Chemistry ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Bioactive Molecules ◽  
Phase Synthesis ◽  
Modular Synthesis ◽  
Wide Range ◽  
Up Scaling

Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described.

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.

scholarly journals Recovery, Purification, and Reusability of Building Blocks for Solid Phase Synthesis

2019 ◽  
Vol 41 (2) ◽  
pp. 1900473
Author(s):  
Fadi Shamout ◽  
Lukas Fischer ◽  
Nicole L. Snyder ◽  
Laura Hartmann
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

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.

Concise solid-phase synthesis of inverse poly(amidoamine) dendrons using AB2 building blocks

2013 ◽  
Vol 49 (51) ◽  
pp. 5784 ◽  
Author(s):  
Adela Ya-Ting Huang ◽  
Ching-Hua Tsai ◽  
Hsing-Yin Chen ◽  
Hui-Ting Chen ◽  
Chi-Yu Lu ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

scholarly journals Modular automated solid phase synthesis of dermatan sulfate oligosaccharides

2014 ◽  
Vol 50 (15) ◽  
pp. 1875-1877 ◽  
Author(s):  
Jeyakumar Kandasamy ◽  
Frank Schuhmacher ◽  
Heung Sik Hahm ◽  
James C. Klein ◽  
Peter H. Seeberger
Keyword(s):  
Solid Phase Synthesis ◽  
Dermatan Sulfate ◽  
Solid Phase ◽  
Building Blocks ◽  
Automated Synthesis ◽  
Phase Synthesis ◽  
Iduronic Acid

Orthogonally protected d-galactosamine and l-iduronic acid building blocks and a photo-cleavable linker are instrumental for the automated synthesis of dermatan sulfate oligosaccharides.

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