scholarly journals Green Solvent Mixtures for Solid-Phase Peptide Synthesis: A Dimethylformamide-Free Highly Efficient Synthesis of Pharmaceutical-Grade Peptides

2019 ◽  
Vol 7 (15) ◽  
pp. 12867-12877 ◽  
Author(s):  
Lucia Ferrazzano ◽  
Dario Corbisiero ◽  
Giulia Martelli ◽  
Alessandra Tolomelli ◽  
Angelo Viola ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solvent Mixtures ◽  
Green Solvent ◽  
Efficient Synthesis ◽  
Highly Efficient

Efficient synthesis of glycopeptide-α-thioesters with a high-mannose type oligosaccharide by means of tert-Boc-solid phase peptide synthesis

2012 ◽  
Vol 364 ◽  
pp. 41-48 ◽  
Author(s):  
Yutaka Makimura ◽  
Tatsuto Kiuchi ◽  
Masayuki Izumi ◽  
Simone Dedola ◽  
Yukishige Ito ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Efficient Synthesis ◽  
High Mannose

scholarly journals Harnessing polarity and viscosity to identify green binary solvent mixtures as viable alternatives to DMF in solid-phase peptide synthesis

2021 ◽  
Author(s):  
Vincent Martin ◽  
Sandip Jadhav ◽  
Peter H. G. Egelund ◽  
Raphael Liffert ◽  
Henrik Johansson Castro ◽  
...  
Keyword(s):  
Pharmaceutical Industry ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Sequence ◽  
Binary Solvent ◽  
Solvent Mixtures ◽  
Binary Solvent Mixtures

Solid-phase peptide synthesis (SPPS) enables routine synthesis of virtually any type of peptide sequence and is the preferred method for peptide synthesis in academia and the pharmaceutical industry alike. Still,...

scholarly journals Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 4004 ◽  
Author(s):  
Ashish Kumar ◽  
Anamika Sharma ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Ring Opening ◽  
Solid Phase ◽  
Theoretical Calculations ◽  
Solid Phase Peptide Synthesis ◽  
Time Dependent ◽  
Green Solvent ◽  
Protecting Group ◽  
Fmoc Protecting Group

GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal.

Efficient synthesis of protected l-phosphonophenylalanine (Ppa) derivatives suitable for solid phase peptide synthesis

2007 ◽  
Vol 48 (23) ◽  
pp. 4051-4054 ◽  
Author(s):  
Satendra S. Chauhan ◽  
Arti Varshney ◽  
Bhavana Verma ◽  
Michael W. Pennington
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Efficient Synthesis

scholarly journals Replacing DMF in solid-phase peptide synthesis: Varying the composition of green binary solvent mixtures as a tool to mitigate common side-reactions

2021 ◽  
Author(s):  
Sandip Jadhav ◽  
Vincent Martin ◽  
Peter H. G. Egelund ◽  
Henrik Johansson Castro ◽  
Tobias Krüeger ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Environmentally Benign ◽  
Side Reactions ◽  
Binary Solvent ◽  
Solvent Mixtures ◽  
Binary Solvent Mixtures ◽  
Made In

Significant efforts have been made in recent years to identify more environmentally benign and less hazardous alternatives to N,N-dimethylformamide (DMF) in solid-phase peptide synthesis (SPPS). Several greener solvents have been...

scholarly journals Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis

2017 ◽  
Vol 58 (4) ◽  
Author(s):  
Javier Eduardo García Castañeda ◽  
Cristian Francisco Vergel Galeano ◽  
Zuly Jenny Rivera Monroy ◽  
Javier Eduardo Rosas Pérez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Synthetic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Amino Group ◽  
Efficient Synthesis ◽  
Phase Synthesis

<p>Solid phase peptide synthesis using the Fmoc/<em>t</em>-Bu strategy (SPPS-Fmoc/tBu) is the most widely used methodology for obtaining synthetic peptides. In this paper, we evaluate the viability of using 4-methylpiperidine as a reagent for deprotection of the amino acid alpha amino group in SPPS-Fmoc/tBu. For this purpose, the peptide (RRWQWRMKKLG) was simultaneously synthesized using 4-methylpiperidine or piperidine for Fmoc removal reagent. The obtained products had similar purities and yields. Finally, 21 peptides were synthesized using 4-methylpiperidine. Our results suggest that is possible to obtain synthetic peptides efficiently by the strategy SPPS-Fmoc/tBu when 4-methylpiperidine was used as reagent to remove Fmoc groups N-alpha protected amino acids.</p>

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