Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern

2014 ◽  
Vol 20 (9) ◽  
pp. 725-735 ◽  
Author(s):  
Stancho Stanchev ◽  
Zbigniew Zawada ◽  
Lenka Monincová ◽  
Lucie Bednárová ◽  
Jiřina Slaninová ◽  
...  
Keyword(s):  
Disulfide Bridge ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Bridge Pattern

scholarly journals Autocatalytic and oscillatory reaction networks that form guanidines and products of their cyclization

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Alexander I. Novichkov ◽  
Anton I. Hanopolskyi ◽  
Xiaoming Miao ◽  
Linda J. W. Shimon ◽  
Yael Diskin-Posner ◽  
...  
Keyword(s):  
Chemical Cues ◽  
Native Chemical Ligation ◽  
Reaction Networks ◽  
Oscillatory Reaction ◽  
Experimental Conditions ◽  
Chemical Ligation ◽  
Chemical Systems ◽  
Life On Earth ◽  
Emergence Of Life ◽  
Equilibrium Chemical

AbstractAutocatalytic and oscillatory networks of organic reactions are important for designing life-inspired materials and for better understanding the emergence of life on Earth; however, the diversity of the chemistries of these reactions is limited. In this work, we present the thiol-assisted formation of guanidines, which has a mechanism analogous to that of native chemical ligation. Using this reaction, we designed autocatalytic and oscillatory reaction networks that form substituted guanidines from thiouronium salts. The thiouronium salt-based oscillator show good stability of oscillations within a broad range of experimental conditions. By using nitrile-containing starting materials, we constructed an oscillator where the concentration of a bicyclic derivative of dihydropyrimidine oscillates. Moreover, the mixed thioester and thiouronium salt-based oscillator show unique responsiveness to chemical cues. The reactions developed in this work expand our toolbox for designing out-of-equilibrium chemical systems and link autocatalytic and oscillatory chemistry to the synthesis of guanidinium derivatives and the products of their transformations including analogs of nucleobases.

scholarly journals Oxo-ester Mediated Native Chemical Ligation: Concept and Applications

2008 ◽  
Vol 130 (47) ◽  
pp. 15814-15816 ◽  
Author(s):  
Qian Wan ◽  
Jin Chen ◽  
Yu Yuan ◽  
Samuel J. Danishefsky
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation
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