Cited by 22Chemical Synthesis and AnalysisAdvanced Synthetic Organic ChemistryBiochemical and Structural Characterization

Multigram-Scale Synthesis of Short Peptides via a Simplified Repetitive Solution-Phase Procedure

Meneses, Célia, Nicoll, Sarah L., Trembleau, Laurent·2010·The Journal of Organic Chemistry

Abstract

A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluorophenyl active esters in a THF/water solvent mixture. Due to their poor solubility, peptide acid intermediates are easily isolated in high purity by acidification under controlled conditions and removal of excess active esters by selective extraction. Contrary to modern repetitive solution-phase peptide synthesis procedures, our approach does not require time-consuming neutralization reactions and reduces significantly the number of operation units that are necessary to obtain peptide intermediates. Efficiency of the method was demonstrated by the rapid synthesis of short hydrophobic and hydrophilic peptides, the antimalarial cycloheptapeptide mahafacyclin B, and a protected form of the hydrophilic pentapeptide GRGDS.

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Crossref · 10.1021/jo902116p

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  • While some optimizations have been performed, a practical strategy for N → C peptide synthesis using unprotected amino acids remains unavailable.

    “While some optimizations have been performed, practical strategy remains unavailable.21”

    From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [21]

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Authors
Meneses, C., Nicoll, S. L., & Trembleau, L.
Affiliations
University of Aberdeen (GB)
Venue
The Journal of Organic Chemistry
Published
2009-12-31
Volume
75
Issue
3
Pages
564-569
ISSN
  • 0022-3263 (ISSN-L)
  • 1520-6904
OpenAlex
W2036602792
Cited by
22
References
30
Citations by year
2026: 1 · 2025: 2 · 2024: 4 · 2023: 1 · 2022: 2 · 2021: 2 · 2020: 1 · 2019: 2 · 2017: 1 · 2016: 1 · 2015: 1 · 2014: 1 · 2013: 2 · 2012: 1
FWCI
0.13
Type
journal article
Language
en
Open access
closed
Locations
  • The Journal of Organic Chemistry (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biochemical and Structural Characterization
MeSH terms
Amino Acid Sequence, Esters, Oligopeptides, Peptides, Peptides, Cyclic, Solubility, Solutions, Solvents, Stereoisomerism, Hydrophobic and Hydrophilic Interactions

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