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US 8,569,452 B2Granted
Preparation of phalloidin and its derivatives
AssigneeAmerican Peptide Company, Inc.
InventorsBaosheng Liu, Jianheng Zhang
Life of this patent
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Abstract
The present invention relates to novel phalloidin derivatives and their fluorescent dye conjugates. These new compounds may be used in studies of actin dynamics in living systems. The present invention also relates to methods for preparing such compounds. The synthesis routes combine solid-phase and solution phase peptide synthesis, and has great advantage for efficient preparation of a diverse library of the phalloidin derivatives, especially for the synthesis of phalloidin.
Claims9
A method of making the following compound:
- wherein R1, R2, R3 are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkylaryl, heteroaryl, acyl, acylalkyl, carboxy, carboxamido, trialkylsilyl, aryldialkyl, hydroxy, alkoxy, aryloxy, heteroaryloxy, chloro, bromo, fluoro, iodo, thio, alkylthio, arylthio, acyclthio, amino, alkylamino, dialkylamino, acylamino, arylamino, diarylamino, carboxamido;
- and wherein the method comprises the following steps:
- a) synthesizing a linear heptapeptide on a resin;
- b) cleaving the linear heptapeptide from the resin;
- c) performing head-to-tail coupling on the heptapeptide to produce a cyclic peptide;
- d) forming a thioether by direct indole thionation
- thereby making the compound.
4 more elements
Dependencies are inferred from the claim text.