Synthesis of <Emphasis Type="Italic">P,N</Emphasis>-protected phosphinic pseudoprolylglycine block |
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| Authors: | A V Vinyukov M E Dmitriev A V Afanas’ev V V Ragulin L A Andreeva N F Myasoedov |
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| Institution: | 1.Institute of Physiologically Active Compounds,Russian Academy of Sciences,Chernogolovka, Moscow oblast,Russia;2.Chembridge Ltd.,Moscow,Russia;3.Institute of Molecular Genetics,Russian Academy of Sciences,Moscow,Russia |
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| Abstract: | The phosphine block N-Cbz-Pro-ψP(O)(OAd)CH2]-GlyOH has been synthesized for subsequent peptide assembly. A procedure has been proposed for the preparation of phosphorus prolylglycine isostere by three-center two-component amide version of the Kabachnik–Fields reaction. A combination of amide and carbonyl fragments in the molecule of 4-N-Cbz-aminobutyraldehyde makes it possible to accomplish cyclization with generation in situ of a cyclic pyrrolidine Schiff base, followed by Arbuzov phosphorylation of the latter with diacetyl 2-(ethoxycarbonyl)ethyl phosphonite generated in situ. |
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