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- W209426244 abstract "CuOOH-mediated inactivation of P450s results in their prosthetic heme degradation to products that alkylate the apoprotein. Indirect approaches suggest that this alkylation occurs at the active site. To identify the specific apoprotein site(s) alkylated, purified {sup 3}H-or {sup 14}C-heme labeled P450 2B1 incubated with CuOOH, was subjected to lysyl endopeptidase-C digestion. Two major peaks (L1 and L2) containing {sup 3}H- or {sup 14}C-labeled peptides were detected by reverse-phase HPLC of the digest (C4 column; linear solvent gradient: 15 to 85% B (iPrOH:acetonitrile, 1:1; 0.08% HFBA)/120 min; A (H{sub 2}O/0.1% HFBA)). L1 (eluting at {approx} 65% solvent B) contained the highest specific radioactivity and after tricine-SDS PAGE yielded 3 peptide bands (MW {approx} 3,000 (P1), 5,000 (P2) and 8,000 (P3)). Although all 3 bands were found radiolabeled, the yield of P1 was higher than that of P2 or P3. Amino acid (AA) sequence analysis of the first 13 N-terminal residues of P1 revealed the sequence RICLGEGIARNEL, corresponding to residues 434-446 of the reported 2B1 sequence. A peptide with the molecular mass of 3,771 was detected in preliminary electrospray mass spectrometric analysis of L1. Since the mass calculated for the AA composition of the predicted peptide (434-466) is 3,722, the additional 49more » mass units apparently are contributed by the alkylating heme fragment. This alkylated 2B1 sequence contains Cys{sub 436}, the conserved residue that provides the SH-ligand for heme, and therefore corresponds to the heme-sandwiching helix L of P450 101. Thus, these findings indicate the heme alkylation occurs at the 2B1 active site, thereby qualifying the process as truly suicidal.« less" @default.
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- W209426244 date "1992-02-26" @default.
- W209426244 modified "2023-09-24" @default.
- W209426244 title "Cumene hydroperoxide (CuOOH) inactivated cytochrome P450 2B1: Identification of an active site heme-alkylated peptide" @default.
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