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J. Biol. Chem., Vol. 265, Issue 27, 16248-16254, Sep, 1990
RC Stephenson and S Clarke
Polypeptides synthesized in eucaryotic cells with a C-terminal -Cys-Xaa-
Xaa-Xaa (-CXXX) sequence are candidates for post-translational
modifications that include the removal of the last 3 amino acids and the
lipidation and methyl esterification of the cysteinyl residue. To
characterize the methylation reaction in vitro, the peptide Leu-Ala-Arg-
Tyr-Lys-Cys (LARYKC) and its S-isoprenylated and S-alkylated derivatives
were synthesized and assayed as methyl-accepting substrates with
subcellular fractions of rat tissues including liver microsomal membranes.
While little or no peptide-specific methyltransferase activity was detected
in the latter preparation using the unmodified hexapeptide, the C10, C15,
and C20 isoprenylated derivatives were substrates with Km values of 389
microM for S-geranyl-LARYKC, 2.2 microM for S-farnesyl-LARYKC, and
approximately 10.9 microM for S- geranylgeranyl-LARYKC. The methyl-acceptor
activities of a variety of n- alkyl S-derivatives of LARYKC (C8, C10, C13,
C15) were also tested; all of these compounds were poorer substrates than
the S-geranyl derivative. This enzyme activity uses S-adenosyl-L-methionine
as the methyl donor (Km = 2.1 microM) and can be inhibited by S-
adenosylhomocysteine (Ki = 9.2 microM), a product of the methylation
reaction. The S-farnesyl-LARYKC peptide can inhibit the carboxyl
methylation of bovine retinal rod outer segment membrane proteins that was
previously shown to occur at the alpha-carboxyl group of C-terminal
cysteine residues, demonstrating that the same enzyme can methylate both
peptides and proteins. These results suggest that the methyl esterification
of proteins containing a C-terminal -CXXX sequence requires not only the
removal of the 3 terminal amino acids, but the isoprenylation of the
sulfhydryl group as well.
Identification of a C-terminal protein carboxyl methyltransferase in rat liver membranes utilizing a synthetic farnesyl cysteine-containing peptide substrate
Department of Chemistry and Biochemistry, University of California, Los Angeles 90024.
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