Paper
Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters.
Published Sep 9, 2011 · H. Hojo, Hajime Kobayashi, R. Ubagai
Organic & biomolecular chemistry
Q2 SJR score
20
Citations
0
Influential Citations
Abstract
The synthesis of Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, an N- to S-acyl migratory device for the preparation of peptide thioesters by Fmoc-SPPS (solid-phase peptide synthesis) is described. Condensation of Fmoc-aminoacyl pentafluorophenyl ester and N-ethyl-S-triphenylmethylcysteine was efficiently performed in the presence of HOOBt (3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine) in DMF. A small amount of diastereomer yielded during the reaction was easily separated by HPLC purification and the highly pure devices were obtained for most of the proteinogenic amino acids.
Study Snapshot
This study efficiently synthesized Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, a key device for peptide thioester synthesis, using HOOBt in DMF, resulting in highly pure devices for most protein
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
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Citations
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Cyclic peptides synthesized using N-ethylcysteine-assisted native chemical ligation show good yields and purity, with potential for antimalarial activity against P. falciparum 3D7.
2019·7citations·G. Serra et al.·Chemical communications
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This study presents a one-step method for synthesis of Fmoc-aminoacyl-N-alkylcysteine dipeptide, enabling efficient peptide thioester production through N-alkylcysteine-assisted thioesterification.
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Glycopeptide Synthesis Based on a TFA-Labile Protection Strategy and One-Pot Four-Segment Ligation for the Synthesis of O-Glycosylated Histone H2A
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