Tetramethylfluoroformamidinium Hexafluorophosphate: A Rapid-Acting Peptide Coupling Reagent for Solution and Solid Phase Peptide Synthesis

1995 ◽  
Vol 117 (19) ◽  
pp. 5401-5402 ◽  
Author(s):  
Louis A. Carpino ◽  
Ayman El-Faham
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Coupling ◽  
Coupling Reagent ◽  
Tetramethylfluoroformamidinium Hexafluorophosphate

scholarly journals Cover Picture: Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis (11/2021)

2021 ◽  
Vol 6 (11) ◽  
pp. 2648-2648
Author(s):  
Othman Al Musaimi ◽  
Richard Wisdom ◽  
Peter Talbiersky ◽  
Beatriz G. De La Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis

2021 ◽  
Vol 6 (11) ◽  
pp. 2649-2657
Author(s):  
Othman Al Musaimi ◽  
Richard Wisdom ◽  
Peter Talbiersky ◽  
Beatriz G. De La Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis

2012 ◽  
Vol 18 (3) ◽  
pp. 199-207 ◽  
Author(s):  
Claudia U. Hjørringgaard ◽  
Andreas Brust ◽  
Paul F. Alewood
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

scholarly journals Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis

2018 ◽  
Vol 14 ◽  
pp. 1112-1119 ◽  
Author(s):  
Dan Liu ◽  
Ya-Li Guo ◽  
Jin Qu ◽  
Chi Zhang
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Solid Phase ◽  
Biological Activities ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reaction ◽  
Hypervalent Iodine ◽  
Peptide Coupling ◽  
Cyclic Peptide Synthesis ◽  
Cyclic Heptapeptide

The system of the hypervalent iodine(III) reagent FPID and (4-MeOC6H4)3P was successfully applied to solid-phase peptide synthesis and cyclic peptide synthesis. Four peptides with biological activities were synthesized through SPPS and the bioactive cyclic heptapeptide pseudostellarin D was obtained via solution-phase peptide synthesis. It is worth noting that FPID can be readily regenerated after the peptide coupling reaction.

Improved Fmoc Solid-Phase Peptide Synthesis of Oxytocin with High Bioactivity

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1780-1784 ◽  
Author(s):  
Pengcheng Sun ◽  
Wenli Tang ◽  
Yu Huang ◽  
Bi-Huang Hu
Keyword(s):  
Peptide Synthesis ◽  
Disulfide Bond ◽  
High Purity ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Side Chain ◽  
Protecting Group ◽  
Coupling Reagent

We described here the synthesis of oxytocin by an improved Fmoc solid-phase peptide synthesis (SPPS) method with a Rink-Amide resin as the solid support, HBTU as the coupling reagent, Fmoc-protected amino acids as the building blocks, and piperazine for Fmoc removal as a substitute for the standard reagent piperidine. Unlike previously reported syntheses, the removal of the S-Acm protecting group of Cys and cyclization forming the disulfide bond were carried out by using iodine on the resin with the fully protected peptide chains. Finally, a crude oxytocin with a purity of 92% was obtained by simultaneous cleavage of the peptide chains from the resin and removal of all side-chain protecting groups with trifluoroacetic acid containing the scavengers (yield 85%). The crude peptide was purified by using preparative RP-HPLC to obtain oxytocin (high purity 99.3%) with a bioactivity of 588 IU/mg, the highest reported so far in the literature. This investigation provides a contribution in efforts for the large-scale synthesis of oxytocin in high purity under mild conditions with iodine for on-resin disulfide bond formation and a substitute for the standard Fmoc-deprotecting reagent piperidine, a controlled substance.

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