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A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues

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A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.
OriginalsprogEngelsk
TidsskriftEuropean Journal of Medicinal Chemistry
Vol/bind38
Udgave nummer1
Sider (fra-til)117-22
Antal sider6
ISSN0223-5234
StatusUdgivet - 2003

ID: 42389845