N,N′-Dialkyldiamide-Type Phosphate Protecting Groups for Fmoc Synthesis of Phosphotyrosine-Containing Peptides: Optimization of the Alkyl Group
- 1 August 1998
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 71 (8) , 1887-1898
- https://doi.org/10.1246/bcsj.71.1887
Abstract
Synthesis and evaluation of three Fmoc–phosphotyrosine derivatives with a phosphate group protected as N,N′-dialkyldiamide (alkyl = Prn, Pri, and Bui) were studied. All the derivatives were obtained as crystals, among which the Buiderivative (4c) was the best in ease of preparation and excellence in cleavage property. Solid phase synthesis of a methionine-containing peptide, H–Tyr(PO3H2)–Val–Pro–Met–Leu–OH, could be done without any problems.This publication has 16 references indexed in Scilit:
- N,N′-Dialkyldiamide-type phosphate protecting groups for Fmoc synthesis of phosphotyrosine-containing peptidesTetrahedron Letters, 1996
- Synthesis and Application of Fmoc-O-[Bis(dimethylamino)phosphono]tyrosine, a Versatile Protected Phosphotyrosine EquivalentThe Journal of Organic Chemistry, 1995
- Solid‐phase synthesis of peptides containing phosphoserine using phosphate tert.‐butyl protecting group*International Journal of Peptide and Protein Research, 1990
- FMOC-polyamide solid phase synthesis of an O-phosphotyrosine-containing tridecapeptideTetrahedron Letters, 1989
- Removal of 9-fluorenylmethyloxycarbonyl (Fmoc) group with tetrabutylammonium fluorideTetrahedron Letters, 1987
- A Simple and Effective Chemical Phosphorylation Procedure for BiomoleculesHelvetica Chimica Acta, 1987
- Phosphinyl- and Phosphinothioylamino Acids and Peptides. V. Preparation of Dimethylphosphinothioylamino Acids and Solid Phase Peptide SynthesisBulletin of the Chemical Society of Japan, 1979
- 9-Fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting groupJournal of the American Chemical Society, 1970
- Mechanisms in the Hydrolysis of Phosphorodiamidic Chlorides1Journal of the American Chemical Society, 1965