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

One-pot hydrazide-based native chemical ligation for efficient chemical synthesis and structure determination of toxin Mambalgin-1

2014 ◽  
Vol 50 (44) ◽  
pp. 5837-5839 ◽  
Author(s):  
Man Pan ◽  
Yao He ◽  
Ming Wen ◽  
Fangming Wu ◽  
Demeng Sun ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Snake Venom ◽  
Structure Determination ◽  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation ◽  
Venom Toxin ◽  
Snake Venom Toxin ◽  
Switch Strategy

An efficient one-pot chemical synthesis of snake venom toxin Mambalgin-1 was achieved using an azide-switch strategy combined with hydrazide-based native chemical ligation.

scholarly journals A synthetic approach to ‘click’ neoglycoprotein analogues of EPO employing one-pot native chemical ligation and CuAAC chemistry

2019 ◽  
Vol 10 (3) ◽  
pp. 815-828 ◽  
Author(s):  
D. J. Lee ◽  
A. J. Cameron ◽  
T. H. Wright ◽  
P. W. R. Harris ◽  
M. A. Brimble
Keyword(s):  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
One Pot ◽  
Chemical Ligation ◽  
Synthetic Methodologies

The batch-wise variability of commercial erythropoietin (EPO) preparations warrants development of more advanced synthetic methodologies. We have developed a diverse chemical toolkit to prepare ‘click’ neoglycoprotein variants of EPO.

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.

One-Pot/Sequential Native Chemical Ligation Using Photocaged Crypto-thioester

2016 ◽  
Vol 18 (3) ◽  
pp. 596-599 ◽  
Author(s):  
Keisuke Aihara ◽  
Kosuke Yamaoka ◽  
Naoto Naruse ◽  
Tsubasa Inokuma ◽  
Akira Shigenaga ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation

scholarly journals Thiazolidine Deprotection by 2-Aminobenzamide-Based Aldehyde Scavenger for One-Pot Multiple Peptide Ligation

2021 ◽  
Author(s):  
Koki Nakatsu ◽  
Hitoshi Murakami ◽  
Gosuke Hayashi ◽  
Akimitsu Okamoto
Keyword(s):  
Native Chemical Ligation ◽  
High Yield ◽  
Side Reactions ◽  
Model Peptide ◽  
One Pot ◽  
Chemical Ligation ◽  
Good Ability ◽  
Synthetic Proteins ◽  
Short Time ◽  
Peptide Ligation

Strategies for one-pot peptide ligation enable chemists to access synthetic proteins at a high yield in a short time. Herein, we report a new one-pot multi-segments ligation strategy using N-terminal thiazolidine (Thz) peptide and a formaldehyde scavenger. Among our designed 2-aminobenzamide-based aldehyde scavengers, 2-amino-5-methoxy-N’,N’-dimethylbenzohydrazide showed a good ability to capture formaldehyde from Thz at pH 4.0. This scavenger had compatibility with the conditions of native chemical ligation at pH 7.5. Using this scavenger for a model peptide ligation system, we performed one-pot four-segment ligation at a high yield without significant side reactions.

ChemInform Abstract: Shifting Native Chemical Ligation into Reverse Through N- versus S-Acyl Transfer

ChemInform ◽  
2012 ◽  
Vol 43 (9) ◽  
pp. no-no
Author(s):  
Derek Macmillan ◽  
Anna Adams ◽  
Bhavesh Premdjee
Keyword(s):  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Chemical Ligation

Imidazole-Aided Native Chemical Ligation: Imidazole as a One-Pot Desulfurization-Amenable Non-Thiol-Type Alternative to 4-Mercaptophenylacetic Acid

2016 ◽  
Vol 22 (50) ◽  
pp. 17940-17944 ◽  
Author(s):  
Ken Sakamoto ◽  
Shugo Tsuda ◽  
Masayoshi Mochizuki ◽  
Yukie Nohara ◽  
Hideki Nishio ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation
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