scholarly journals Development of oxetane modified building blocks for peptide synthesis

2020 ◽  
Vol 18 (28) ◽  
pp. 5400-5405 ◽  
Author(s):  
Stefan Roesner ◽  
Jonathan D. Beadle ◽  
Leo K. B. Tam ◽  
Ina Wilkening ◽  
Guy J. Clarkson ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks

The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported.

scholarly journals Reinvestigation of a Critical Reductive Amination Step Leads to an Optimized Protocol for the Synthesis of N-2-Hydroxybenzylcysteine Peptide Crypto-Thioesters

2020 ◽  
Author(s):  
Skander Abboud ◽  
Vincent AUCAGNE
Keyword(s):  
Peptide Synthesis ◽  
Reaction Mechanisms ◽  
Reductive Amination ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Optimized Protocol ◽  
Depth Study

An in-depth study of the Fmoc-based solid phase peptide synthesis of N-Hnb-Cys crypto-thioester peptides, advantageous building blocks for the native chemical ligation-based synthesis of proteins, led to the identification of epimerized and imidazolidinone side products formed during a key reductive amination step. The understanding of the underlying reaction mechanisms was crucial for the developement of an automatable optimized synthetic protocol.

Caged Phospho-Amino Acid Building Blocks for Solid-Phase Peptide Synthesis

2003 ◽  
Vol 68 (17) ◽  
pp. 6795-6798 ◽  
Author(s):  
Deborah M. Rothman ◽  
M. Eugenio Vazquez ◽  
Elizabeth M. Vogel ◽  
Barbara Imperiali
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks

scholarly journals Convergent Synthesis of Thioether Containing Peptides

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 218
Author(s):  
Spyridon Mourtas ◽  
Christina Katakalou ◽  
Dimitrios Gatos ◽  
Kleomenis Barlos
Keyword(s):  
Carboxylic Acids ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Solid Support ◽  
Convergent Synthesis ◽  
Fmoc Group ◽  
Synthetic Routes ◽  
Peptide Elongation

Thioether containing peptides were obtained following three synthetic routes. In route A, halo acids esterified on 2-chlorotrityl(Cltr) resin were reacted with N-fluorenylmethoxycarbonyl (Fmoc) aminothiols. These were either cleaved from the resin to the corresponding (Fmoc-aminothiol)carboxylic acids, which were used as key building blocks in solid phase peptide synthesis (SPPS), or the N-Fmoc group was deprotected and peptide chains were elongated by standard SPPS. The obtained N-Fmoc protected thioether containing peptides were then condensed either in solution, or on solid support, with the appropriate amino components of peptides. In route B, the thioether containing peptides were obtained by the reaction of N-Fmoc aminothiols with bromoacetylated peptides, which were synthesized on Cltr-resin, followed by removal of the N-Fmoc group and subsequent peptide elongation by standard SPPS. In route C, the thioether containing peptides were obtained by the condensation of a haloacylated peptide synthesized on Cltr-resin and a thiol-peptide synthesized either on 4-methoxytrityl(Mmt) or trityl(Trt) resin.

Diaminodiacid-based solid-phase synthesis of all-hydrocarbon stapled α-helical peptides

2015 ◽  
Vol 13 (22) ◽  
pp. 6286-6290 ◽  
Author(s):  
Feng-Liang Wang ◽  
Ye Guo ◽  
Si-Jian Li ◽  
Qing-Xiang Guo ◽  
Jing Shi ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Helical Peptides ◽  
Phase Synthesis

An alternative stapling strategy is described herein using Fmoc-solid phase peptide synthesis (SPSS) that employed pre-prepared diaminodiacid building blocks to introduce all-hydrocarbon staples into peptides by on-resin cyclization.

Arylboronate Ester Protected Amino Acids as Orthogonal Building Blocks for Fmoc Solid-Phase Peptide Synthesis

2017 ◽  
Vol 2017 (39) ◽  
pp. 5916-5920 ◽  
Author(s):  
Chao Liu ◽  
Yan Zou ◽  
Hui Song ◽  
Yuan-Ye Jiang ◽  
Hong-Gang Hu
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks

Nα-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

2018 ◽  
Vol 16 (29) ◽  
pp. 5359-5362 ◽  
Author(s):  
Eva Schütznerová ◽  
Adam Přibylka ◽  
Viktor Krchňák
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Design Synthesis ◽  
Mild Conditions ◽  
Privileged Structures

Fmoc-protected Nα-amino acid containing heterocyclic privileged structures, O-(1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)-l-serine and O-((S)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)-l-serine, were synthesized on the solid phase from simple commercially available building blocks under mild conditions.

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