AJIPHASE®: A Highly Efficient Synthetic Method for One-Pot Peptide Elongation in the Solution Phase by an Fmoc Strategy

Angewandte Chemie
Daisuke TakahashiTatsuya Fukui

Abstract

We previously reported an efficient peptide synthesis method, AJIPHASE®, that comprises repeated reactions and isolations by precipitation. This method utilizes an anchor molecule with long-chain alkyl groups as a protecting group for the C-terminus. To further improve this method, we developed a one-pot synthesis of a peptide sequence wherein the synthetic intermediates were isolated by solvent extraction instead of precipitation. A branched-chain anchor molecule was used in the new process, significantly enhancing the solubility of long peptides and the operational efficiency compared with the previous method, which employed precipitation for isolation and a straight-chain aliphatic group. Another prerequisite for this solvent-extraction-based strategy was the use of thiomalic acid and DBU for Fmoc deprotection, which facilitates the removal of byproducts, such as the fulvene adduct.

References

Nov 14, 2000·Biopolymers·L AnderssonM Verlander
May 26, 2001·The Journal of Organic Chemistry·A BendavidL Wieczorek
Aug 29, 2002·Chemical Communications : Chem Comm·Kazuhiro ChibaMasahiro Tada
May 15, 2003·Chemical Communications : Chem Comm·Mamoru MizunoToshiyuki Inazu
Jul 8, 2011·Bioorganic & Medicinal Chemistry Letters·Shingo KitadaKazuhiro Chiba
Dec 3, 2014·Drug Discovery Today·Keld Fosgerau, Torsten Hoffmann

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Citations

Mar 29, 2019·Current Protocols in Nucleic Acid Chemistry·Alejandro Gimenez Molina, Yogesh S Sanghvi
Jan 15, 2021·Angewandte Chemie·Jet YeoAndrew Livingston
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shinya YanoHideki Kubota
Mar 23, 2019·The Journal of Organic Chemistry·Albert Isidro-LlobetFrank Roschangar
Nov 23, 2021·The Journal of Organic Chemistry·Xuan ZhouXianglin Shi

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Software Mentioned

AJIPHASE®
SPPS
AJPHASE

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