Synthesis and Fungicidal Activity of Lipophylic N- and O-Acyl Derivatives of β-Hydroxy ᴅʟ-α-Amino Acids

Abstract

Synthesis of N- and O-acyl derivatives of ᴅʟ-serine and threo-ᴅʟ-phenylserine was accomplished by a regioselective acylation of the corresponding amino acid. The residues introduced into amino acid structure contain hydrophobic long chain or aromatic, namely lauroyl, myristoyl and phenylacetyl moieties. The fungicidal activity against six strains of fungi was studied. Several compounds were found to be effective against growth of fungi, and Omyristoyl- ᴅʟ-serine 2 and N-phenylacetyl-threo-ᴅʟ-phenylserine 8 completely inhibited the growth of the mycelium of the fungus Verticillium dahliae.

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

“…While it is true that a number of convenient techniques for chemoselective O -acylations were developed during this time period, the application of these techniques nevertheless seems to have been strictly confined to biologically oriented chemistry, as a set of specialized techniques, useful for certain applications in peptide chemistry or in the synthesis of medicinal compounds from tyrosine or L-DOPA, besides, of course, the preparation and study of such O -acylated amino acids in itself. The employment of acidic O -acylations of hydroxyamino acids as a tool for such purposes would continue to flourish, and has to a certain extent remained to do so, for instance as a method for chemoselective O - and S -palmitoylation of peptides [ 39 ], as reported in 1999 (using palmitoyl chloride in CF 3 CO 2 H) or in the synthesis of O -lauroyl, O -myristoyl and O -phenylacetyl derivatives of DL-serine and threo-DL-phenylserine, as reported in 2003 (using the acyl chlorides in CF 3 CO 2 H), derivatives that displayed fungicidal activity [ 40 ]. However, by and large, the synthesis of amino acid or amino alcohol derivatives has relied on traditional protective group chemistry, much due to the pervasive role of flash column chromatography in modern organic synthesis.…”