Novel diphenylmethyl-Derived Amide Protecting Group for Efficient Liquid-Phase Peptide Synthesis: AJIPHASE
- 24 August 2012
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (17), 4514-4517
- https://doi.org/10.1021/ol302002g
Abstract
An efficient method for the synthesis of peptides bearing an amide at the C-terminal is described. This method involves the attachment of a C-terminal protecting group bearing long aliphatic chains, followed by the repetition of simple reaction and precipitation steps with the combined advantages of liquid-phase peptide synthesis (LPPS) and solid-phase peptide synthesis (SPPS). Using this method, a hydrophobic peptide was successfully synthesized in good yield and high purity, which cannot be obtained satisfactorily by SPPS.Keywords
This publication has 12 references indexed in Scilit:
- Solution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tagTetrahedron, 2011
- Hydrophobic tag-assisted liquid-phase synthesis of a growth hormone-inhibiting peptide somatostatinBioorganic & Medicinal Chemistry Letters, 2011
- Synthetic therapeutic peptides: science and marketDrug Discovery Today, 2010
- DioRaSSP: Diosynth Rapid Solution Synthesis of PeptidesOrganic Process Research & Development, 2005
- A novel peptide synthesis using fluorous chemistryChemical Communications, 2003
- Rapid, Continuous Solution-Phase Peptide Synthesis: Application to Peptides of Pharmaceutical InterestOrganic Process Research & Development, 2002
- A Novel Protecting Group for Constructing Combinatorial Peptide LibrariesBulletin of the Chemical Society of Japan, 2001
- Large-scale synthesis of peptidesBiopolymers, 2000
- New, easily removable poly(ethylene glycol) supports for the liquid-phase method of peptide synthesisThe Journal of Organic Chemistry, 1980
- Liquid-phase Peptide Synthesis by Fragment Condensation on a Soluble Polymer Support. III. The Influence of the Content and the Chain Length of a Peptide Anchored to a Soluble Polymer Support on the Reactivity of the Amino-free Terminal of the PeptideBulletin of the Chemical Society of Japan, 1980