N,N'-DIALKYLDIAMIDE-TYPE PHOSPHATE PROTECTING GROUPS FOR FMOC SYNTHESIS OF PHOSPHOTYROSINE-CONTAINING PEPTIDES - OPTIMIZATION OF THE ALKYL GROUP

Authors
UEKI M GOTO R OKUMURA J ISHII K
Citation
M. Ueki et al., N,N'-DIALKYLDIAMIDE-TYPE PHOSPHATE PROTECTING GROUPS FOR FMOC SYNTHESIS OF PHOSPHOTYROSINE-CONTAINING PEPTIDES - OPTIMIZATION OF THE ALKYL GROUP, Bulletin of the Chemical Society of Japan, 71(8), 1998, pp. 1887-1898
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
71
Issue
8
Year of publication
1998
Pages
1887 - 1898
Database
ISI
SICI code
0009-2673(1998)71:8<1887:NPPGFF>2.0.ZU;2-Y
Abstract
Synthesis and evaluation of three Fmoc-phosphotyrosine derivatives wit h a phosphate group protected as N,N'-dialkyldiamide (alkyl = Pr-n, Pr -i, and Bu-i) were studied. All the derivatives were obtained as cryst als, among which the Bu-i derivative (4c) was the best in ease of prep aration and excellence in cleavage property. Solid phase synthesis of a methionine-containing peptide, H-Tyr(PO3H2)-Val-Pro-Met-Leu-OH, coul d be done without any problems.