Synthetic Procedure for N-Fmoc Amino Acyl-N-Sulfanylethylaniline Linker as Crypto-Peptide Thioester Precursor with Application to Native Chemical Ligation

2012 ◽  
Vol 77 (16) ◽  
pp. 6948-6958 ◽  
Author(s):  
Ken Sakamoto ◽  
Kohei Sato ◽  
Akira Shigenaga ◽  
Kohei Tsuji ◽  
Shugo Tsuda ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Synthetic Procedure ◽  
Peptide Thioester

Synthesis of misfolded glycoprotein dimers through native chemical ligation of a dimeric peptide thioester

2016 ◽  
Vol 14 (25) ◽  
pp. 6088-6094 ◽  
Author(s):  
Masayuki Izumi ◽  
Shinji Komaki ◽  
Ryo Okamoto ◽  
Akira Seko ◽  
Yoichi Takeda ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Thioester

Misfolded glycoprotein dimers were synthesized through double native chemical ligation between a dimeric peptide-α-thioester, glycopeptide, and non-glycosylated peptide.

scholarly journals Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation

2017 ◽  
Vol 8 (1) ◽  
pp. 117-123 ◽  
Author(s):  
Hader E. Elashal ◽  
Yonnette E. Sim ◽  
Monika Raj
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solid Support ◽  
Native Chemical Ligation ◽  
Selective Activation ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

scholarly journals A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters

2016 ◽  
Vol 7 (1) ◽  
pp. 339-345 ◽  
Author(s):  
Victor P. Terrier ◽  
Hélène Adihou ◽  
Mathieu Arnould ◽  
Agnès F. Delmas ◽  
Vincent Aucagne
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Straightforward Method ◽  
Peptide Thioester

A bio-inspired method for the synthesis of peptide thioester surrogates for native chemical ligation was developed. The process can be fully automated and does not require postsynthetic steps.

Palladium mediated deallylation in fully aqueous conditions for native chemical ligation at aspartic and glutamic acid sites

2018 ◽  
Vol 16 (22) ◽  
pp. 4061-4064 ◽  
Author(s):  
Muhammad Jbara ◽  
Emad Eid ◽  
Ashraf Brik
Keyword(s):  
Glutamic Acid ◽  
Acid Sites ◽  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Aqueous Conditions

An efficient native chemical ligation approach at Asp and Glu sites is reported applying a hydrazide precursor, as a peptide thioester, and allyl protection at the side chain of Asp and Glu.

Peptidyl N-alkylcysteine as a peptide thioester surrogate in the native chemical ligation

2015 ◽  
Vol 56 (11) ◽  
pp. 1370-1373 ◽  
Author(s):  
Yuya Asahina ◽  
Kei Nabeshima ◽  
Hironobu Hojo
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Thioester

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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