Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones

RSC Advances ◽  
2016 ◽  
Vol 6 (14) ◽  
pp. 11528-11535 ◽  
Author(s):  
Ajjampura C. Vinayaka ◽  
Toreshettahally R. Swaroop ◽  
Prasanna Kumara Chikkade ◽  
Kanchugarakoppal S. Rangappa ◽  
Maralinganadoddi P. Sadashiva

The transition-metal-free economical solid phase synthesis of 1,2-disubstituted 4-quinolones has been developed via the novel regiospecific synthesis of enaminones.

2018 ◽  
Vol 3 (45) ◽  
pp. 12946-12950 ◽  
Author(s):  
Delie An ◽  
Wenkang Song ◽  
Zhihong Peng ◽  
Yingjun Zhang ◽  
Wanrong Dong

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1872 ◽  
Author(s):  
Ondřej Kostov ◽  
Radek Liboska ◽  
Ondřej Páv ◽  
Pavel Novák ◽  
Ivan Rosenberg

We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands.


2021 ◽  
Vol 304 ◽  
pp. 122548
Author(s):  
Feiyi Lyu ◽  
Zhuo Chen ◽  
Ruowen Shi ◽  
Jiase Yu ◽  
Bo-Lin Lin

2016 ◽  
Vol 12 ◽  
pp. 2556-2562 ◽  
Author(s):  
Elisabeth Mairhofer ◽  
Elisabeth Fuchs ◽  
Ronald Micura

Access to 3-deazaadenosine (c3A) building blocks for RNA solid-phase synthesis represents a severe bottleneck in modern RNA research, in particular for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, we report the 5-step synthesis of a c3A phosphoramidite from cost-affordable starting materials. The key reaction is a silyl-Hilbert–Johnson nucleosidation using unprotected 6-amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling.


2001 ◽  
Vol 113 (24) ◽  
pp. 4765-4768 ◽  
Author(s):  
Ignacio Vargas-Baca ◽  
Debbie Mitra ◽  
Holly J. Zulyniak ◽  
Jay Banerjee ◽  
Hanadi F. Sleiman

Author(s):  
Ignacio Vargas-Baca ◽  
Debbie Mitra ◽  
Holly J. Zulyniak ◽  
Jay Banerjee ◽  
Hanadi F. Sleiman

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 813 ◽  
Author(s):  
Kinga Hartman ◽  
Przemyslaw Mielczarek ◽  
Jerzy Silberring

This work presents the synthesis of the novel covalent inhibitor of cysteine proteases where epoxide has been replaced by the iodoacetyl functional group. The molecule, similar in action to E-64 and DCG-04, the commonly applied inhibitors, is additionally biotinylated and contains tyrosyl iodination sites. The Fmoc solid phase synthesis has been applied. Conjugation of iodoacetic acid with the peptide was optimized by testing different conjugation agents. The purity of the final product was verified by mass spectrometry and its bioactivity was tested by incubation with a model cysteine protease—staphopain C. Finally, it was shown that the synthesized inhibitor binds to the protein at the ratio of 1:1. More detailed analysis by means of tandem mass spectrometry proved that the inhibitor binds to the cysteine present in the active site of the enzyme.


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