scholarly journals A backbone amide protecting group for overcoming difficult sequences and suppressing aspartimide formation

2016 ◽  
Vol 22 (5) ◽  
pp. 360-367 ◽  
Author(s):  
Abu‐Baker M. Abdel‐Aal ◽  
George Papageorgiou ◽  
Richard Raz ◽  
Martin Quibell ◽  
Fabienne Burlina ◽  
...  
Keyword(s):  
Protecting Group ◽  
Backbone Amide ◽  
Aspartimide Formation ◽  
Difficult Sequences

ChemInform Abstract: A Reversible Protecting Group for the Amide Bond in Peptides. Use in the Synthesis of ′Difficult Sequences′.

ChemInform ◽  
2010 ◽  
Vol 24 (23) ◽  
pp. no-no
Author(s):  
T. JOHNSON ◽  
M. QUIBELL ◽  
D. OWEN ◽  
R. C. SHEPPARD
Keyword(s):  
Amide Bond ◽  
Protecting Group ◽  
Difficult Sequences

scholarly journals Cyanosulfurylides (CSY): Carboxylic Acid Protecting Groups That Prevent Aspartimide Formation During Peptide Synthesis

2019 ◽  
Author(s):  
Kevin Neumann ◽  
Jakob Farnung ◽  
Simon Baldauf ◽  
Jeffrey Bode
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Bond Cleavage ◽  
Solid Phase Peptide Synthesis ◽  
Academic Research ◽  
Industrial Applications ◽  
Protecting Group ◽  
Peptide Chemistry ◽  
Formidable Challenge ◽  
Aspartimide Formation

Peptide chemistry has made great progress in the last decades but the frequent occurrence of aspartimide formation during peptide synthesis remains a formidable challenge. Aspartimide formation leads to low yields in addition to costly purification steps or even inaccessible peptide sequences, hindering both academic research and industrial applications. Here, we report a new alternative approach to address this longstanding challenge of solid phase peptide synthesis by utilizing cyanosulfurylides to mask carboxylic acids by a stable C–C bond. These functional groups – formally zwitterionic species – are exceptionally stable to all common manipulations and impart improved solubility and processing during peptide synthesis. Deprotection is readily and rapidly achieved under mild, aqueous conditions with electrophilic halogenating agents via a highly selective C–C bond cleavage reaction. This new protecting group was employed for the synthesis a range of peptides and proteins including teduglutide, ubiquitin, and LDLa – a peptide that was not accessible on solid-phase peptide synthesis before due to three aspartimide-prone motifs. This protecting group strategy has the potential to overcome one of the most difficult aspects of modern peptide chemistry.

scholarly journals Cyanosulfurylides (CSY): Carboxylic Acid Protecting Groups That Prevent Aspartimide Formation During Peptide Synthesis

2019 ◽  
Author(s):  
Kevin Neumann ◽  
Jakob Farnung ◽  
Simon Baldauf ◽  
Jeffrey Bode
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Bond Cleavage ◽  
Solid Phase Peptide Synthesis ◽  
Academic Research ◽  
Industrial Applications ◽  
Protecting Group ◽  
Peptide Chemistry ◽  
Formidable Challenge ◽  
Aspartimide Formation

Peptide chemistry has made great progress in the last decades but the frequent occurrence of aspartimide formation during peptide synthesis remains a formidable challenge. Aspartimide formation leads to low yields in addition to costly purification steps or even inaccessible peptide sequences, hindering both academic research and industrial applications. Here, we report a new alternative approach to address this longstanding challenge of solid phase peptide synthesis by utilizing cyanosulfurylides to mask carboxylic acids by a stable C–C bond. These functional groups – formally zwitterionic species – are exceptionally stable to all common manipulations and impart improved solubility and processing during peptide synthesis. Deprotection is readily and rapidly achieved under mild, aqueous conditions with electrophilic halogenating agents via a highly selective C–C bond cleavage reaction. This new protecting group was employed for the synthesis a range of peptides and proteins including teduglutide, ubiquitin, and LDLa – a peptide that was not accessible on solid-phase peptide synthesis before due to three aspartimide-prone motifs. This protecting group strategy has the potential to overcome one of the most difficult aspects of modern peptide chemistry.

scholarly journals A caged sperm-activating peptide that has a photocleavable protecting group on the backbone amide

FEBS Letters ◽  
2002 ◽  
Vol 525 (1-3) ◽  
pp. 20-24 ◽  
Author(s):  
Yoshiro Tatsu ◽  
Takuya Nishigaki ◽  
Alberto Darszon ◽  
Noboru Yumoto
Keyword(s):  
Protecting Group ◽  
Backbone Amide
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