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 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

Organocatalytic asymmetric Michael/hemiketalization/acyl transfer reaction of 1,3-propanediones with (E)-2-(2-nitrovinyl)phenols

2019 ◽  
Vol 17 (7) ◽  
pp. 1718-1721 ◽  
Author(s):  
Nimisha Bania ◽  
Subhas Chandra Pan
Keyword(s):  
Transfer Reaction ◽  
Acyl Transfer ◽  
Keto Ester ◽  
Acyl Transfer Reaction

An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between (E)-2-(2-nitrovinyl)phenols and 1,3-propanediones is disclosed to generate products having keto, ester and nitro functionalities.

Synthesis of strained cyclic peptides via an aza-Michael–acyl-transfer reaction cascade

2012 ◽  
Vol 48 (65) ◽  
pp. 8084 ◽  
Author(s):  
Jochem P. A. Rutters ◽  
Yvette Verdonk ◽  
Remko de Vries ◽  
Steen Ingemann ◽  
Henk Hiemstra ◽  
...  
Keyword(s):  
Cyclic Peptides ◽  
Transfer Reaction ◽  
Acyl Transfer ◽  
Acyl Transfer Reaction

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
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