Fmoc-Based Synthesis of Peptide Thioesters for Native Chemical Ligation Employing atert-Butyl Thiol Linker

2011 ◽  
Vol 13 (7) ◽  
pp. 1606-1609 ◽  
Author(s):  
Richard Raz ◽  
Jörg Rademann
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Thioesters

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 Single addition of an allylamine monomer enables access to end-functionalized RAFT polymers for native chemical ligation

2016 ◽  
Vol 52 (88) ◽  
pp. 12952-12955 ◽  
Author(s):  
Naatasha Isahak ◽  
Guillaume Gody ◽  
Lara R. Malins ◽  
Nicholas J. Mitchell ◽  
Richard J. Payne ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
Functional Monomer ◽  
Chemical Ligation ◽  
Novel Method ◽  
Single Addition ◽  
Raft Polymers ◽  
Peptide Thioesters

A novel method for the introduction of a single protected amine-functional monomer at the chain end of RAFT polymers has been developed to enable native chemical ligation with peptide thioesters.

Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer

2015 ◽  
Vol 51 (35) ◽  
pp. 7554-7557 ◽  
Author(s):  
J. Schmalisch ◽  
O. Seitz
Keyword(s):  
Sh3 Domain ◽  
High Reactivity ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation ◽  
Synthetic Utility ◽  
Peptide Thioesters

The old dog and a new trick; mercaptopropionylcysteine (MPA–Cys) peptide thioesters show a surprisingly high reactivity in native chemical ligation (NCL) and allow thiol-additive free reactions. This facilitates sequential NCL reactions and ligation–desulfurization reactions in one-pot formats. The synthetic utility is demonstrated by the synthesis of a SH3 domain.

scholarly journals Going Round in Circles with N→S Acyl Transfer

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1517-1529 ◽  
Author(s):  
Derek Macmillan
Keyword(s):  
Transfer Reaction ◽  
Peptide Sequence ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Full Potential ◽  
Chemical Ligation ◽  
Peptide Engineering ◽  
Naturally Occurring ◽  
Native Peptide ◽  
Peptide Thioesters

It is not highly sophisticated, yet the N→S acyl transfer reaction of a native peptide sequence potentially fills an important technology gap. While several routes to synthetic peptide thioesters exist, only one is routinely applicable for biologically derived samples. Using the naturally occurring amino acid cysteine as the sole activator for N→S acyl transfer we have demonstrated transformation of synthetic and biologically derived precursors into thioesters for use in Native Chemical Ligation, providing a viable alternative for biological samples. Further refinement will be key to realising the full potential of this intriguing process, and increase the number of applications in peptide engineering and therapeutics.1 Introduction2 N→S acyl transfer in ‘normal’ peptide sequences3 Reduced reactivity of internal Xaa-Cys motifs as an advantage in head-to-tail peptide cyclisation4 Reduced reactivity of internal Xaa-Cys motifs as an advantage in modification and cyclisation of biologically produced precursors5 Hydrazinolysis of Xaa-Cys motifs and the acyl hydrazide as a stable thioester equivalent6 Rapid thioester formation via an N→Se acyl shift7 Outlook and conclusions

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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