scholarly journals Side-Chain Cysteine-Functionalized Poly(2-oxazoline)s for Multiple Peptide Conjugation by Native Chemical Ligation

2015 ◽  
Vol 16 (4) ◽  
pp. 1088-1094 ◽  
Author(s):  
Michael Schmitz ◽  
Matthias Kuhlmann ◽  
Oliver Reimann ◽  
Christian P. R. Hackenberger ◽  
Jürgen Groll
Keyword(s):  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Peptide Conjugation

scholarly journals Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1923-1928 ◽  
Author(s):  
Derek Macmillan ◽  
Durbis Castillo-Pazos
Keyword(s):  
Glutamic Acid ◽  
Chain Length ◽  
Cyclic Peptides ◽  
Fine Tuning ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Popular Method ◽  
Slow Reaction

N→S Acyl transfer is a popular method for the postsynthesis production of peptide C α-thioesters for use in native chemical ligation and for the synthesis of head-to-tail cyclic peptides. Meanwhile thioester formation at the side chain of aspartic or glutamic acids, leading to tail-to-side-chain-cyclized species, is less common. Herein we explore the potential for cysteine to function as a latent thioester when appended to the side chain of glutamic acid. Initial insights gained through study of C-terminal β-alanine as a model for the increased chain length were ultimately applied to peptide macrocyclization. Our results emphasize the increased barrier to acyl transfer at the glutamic acid side chain and indicate how a slow reaction, facilitated by cysteine itself, may be accelerated by fine-tuning of the stereoelectronic environment.

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.

Nucleobase-involved native chemical ligation: a novel reaction between an oxanine nucleobase and N-terminal cysteine for oligonucleotide–peptide conjugation

2020 ◽  
Vol 56 (41) ◽  
pp. 5508-5511
Author(s):  
Eui Kyoung Jang ◽  
Yohei Koike ◽  
Yuko Ide ◽  
Kunihiko Tajima ◽  
Kenji Kanaori ◽  
...  
Keyword(s):  
Transfer Reaction ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Site Specific ◽  
Peptide Conjugation ◽  
Acyl Transfer Reaction ◽  
A Site

A novel nucleobase-involved native chemical ligation (NbCL) that allows a site–specific oligonucleotide–peptide conjugation via a new S–N acyl transfer reaction between an oxanine nucleobase and N-terminal cysteine.

scholarly journals Peptide Conjugation to a Polymer Coating via Native Chemical Ligation of Azlactones for Cell Culture

2016 ◽  
Vol 17 (3) ◽  
pp. 1040-1047 ◽  
Author(s):  
Samantha K. Schmitt ◽  
David J. Trebatoski ◽  
John D. Krutty ◽  
Angela W. Xie ◽  
Benjamin Rollins ◽  
...  
Keyword(s):  
Cell Culture ◽  
Polymer Coating ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Conjugation

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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