Insights into the Mechanism and Catalysis of the Native Chemical Ligation Reaction

2006 ◽  
Vol 128 (20) ◽  
pp. 6640-6646 ◽  
Author(s):  
Erik C. B. Johnson ◽  
Stephen B. H. Kent
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Ligation Reaction

21.11.7 Chemoselective Ligation Methods Based on the Concept of Native Chemical Ligation

2021 ◽  
Author(s):  
L. R. Malins ◽  
R. J. Payne
Keyword(s):  
Peptide Synthesis ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Chemoselective Ligation ◽  
Ligation Reaction ◽  
Recent Developments ◽  
Peptide Ligation

AbstractThis chapter extends from the earlier Science of Synthesis contribution on peptide synthesis (Section 21.11) and focuses on recent developments in chemoselective ligation chemistry based on the logic of native chemical ligation. Synthetic strategies that broaden the scope and versatility of the ligation reaction and that have been widely adopted for the preparation of homogeneous peptides and proteins are highlighted. Methods enabling the efficient preparation of peptide ligation precursors are also included in this chapter.

Cover Picture: Expanded Utility of the Native Chemical Ligation Reaction (Chem. Eur. J. 19/2004)

2004 ◽  
Vol 10 (19) ◽  
pp. 4651-4651
Author(s):  
Dawn S. Y. Yeo ◽  
Rajavel Srinivasan ◽  
Grace Y. J. Chen ◽  
Shao Q. Yao
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Ligation Reaction

One-pot native chemical ligation by combination of two orthogonal thioester precursors

2017 ◽  
Vol 53 (13) ◽  
pp. 2114-2117 ◽  
Author(s):  
Yuya Asahina ◽  
Toru Kawakami ◽  
Hironobu Hojo
Keyword(s):  
Native Chemical Ligation ◽  
Protecting Group ◽  
One Pot ◽  
Chemical Ligation ◽  
Ligation Reaction ◽  
Ligation Method ◽  
Peptide Ligation

We developed a one-pot peptide ligation method using two orthogonal thioester precursors and a protecting group for the ligation reaction between Asp and Cys.

Expanded Utility of the Native Chemical Ligation Reaction

2004 ◽  
Vol 10 (19) ◽  
pp. 4664-4672 ◽  
Author(s):  
Dawn S. Y. Yeo ◽  
Rajavel Srinivasan ◽  
Grace Y. J. Chen ◽  
Shao Q. Yao
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Ligation Reaction

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.

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