Synthesis of hydrazinopeptides using solid-phase N -electrophilic amination: extension to the Fmoc/tert -butyl strategy and chemistry of the N-N bond in strong acid media
- 1 October 1999
- journal article
- research article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 54 (4) , 270-278
- https://doi.org/10.1034/j.1399-3011.1999.00105.x
Abstract
The synthesis of hydrazinopeptides using solid‐phase N‐electrophilic amination was extended to the Fmoc/tert‐butyl strategy. Both Boc/benzyl and Fmoc/tert‐butyl strategies led to the isolation of by‐products arising from the partial instability of the N–N bond during the final cleavage and deprotection step. Two paths of decomposition have been shown: the cleavage of the N–N bond leading to the regeneration of the amine and a Hofmann‐type elimination yielding original dianisyl adducts. Our data suggest that the Fmoc/tert‐butyl strategy is better suited for the synthesis of hydrazinopeptides.Keywords
This publication has 20 references indexed in Scilit:
- Synthesis of lipopeptides using hydrazone chemical ligationChemical Biology & Drug Design, 1998
- Synthesis of hydrazinopeptides using solid phase N-amination. Application to chemical ligationTetrahedron Letters, 1996
- Crystal structure analysis of a β‐turn mimic in hydrazino peptidesInternational Journal of Peptide and Protein Research, 1994
- In situ neutralization in Boc‐chemistry solid phase peptide synthesisInternational Journal of Peptide and Protein Research, 1992
- Preparation of protein conjugates via intermolecular hydrazone linkageBiochemistry, 1986
- Solid Phase SynthesisScience, 1986
- Hydrazinverbindungen als Heterobestandteile in Peptiden. XVIII. Synthese von Eledoisinpeptiden, die α‐Hydrazinopropionsäure enthaltenJournal für Praktische Chemie, 1974
- Negamycin, a novel hydrazide antibioticJournal of the American Chemical Society, 1971
- Isolation, Characterization, and Synthesis of Linatine. A Vitamin B6 Antagonist from Flaxseed (Linum usitatissimum)*Biochemistry, 1967
- Solid Phase Peptide Synthesis. I. The Synthesis of a TetrapeptideJournal of the American Chemical Society, 1963