{
    "accession": "MITE0000450",
    "status": "active",
    "comment": "RebM is the rebeccamycin sugar 4\u2032-O-methyltransferase that catalyzes the final tailoring step in rebeccamycin biosynthesis. It transfers a methyl group from S-adenosyl-L-methionine to the 4\u2032-hydroxy group of 4\u2032-demethylrebeccamycin, forming rebeccamycin and S-adenosyl-L-homocysteine.",
    "changelog": [
        {
            "version": "1",
            "date": "2026-05-15",
            "contributors": [
                "0009-0005-2489-2079"
            ],
            "reviewers": [
                "0000-0002-5203-4662"
            ],
            "comment": "New entry. Reviewer 1 fixed ambiguous stereochemistry in smarts."
        }
    ],
    "enzyme": {
        "name": "RebM",
        "description": "SAM-dependent O-methyltransferase",
        "references": [
            "doi:10.1074/jbc.M800503200",
            "doi:10.1002/cbic.200500504",
            "doi:10.1271/bbb.67.127"
        ],
        "databaseIds": {
            "uniprot": "Q8KZ94",
            "genpept": "BAC10678.1",
            "mibig": "BGC0000821"
        },
        "cofactors": {
            "organic": [
                "SAM"
            ]
        }
    },
    "reactions": [
        {
            "tailoring": [
                "Methylation"
            ],
            "description": "4\u2032-O-methylation of 4\u2032-demethylrebeccamycin to rebeccamycin using SAM as the methyl donor.",
            "reactionSMARTS": "[#8:1]=[#6:2]1-[#7:11]-[#6:9](=[#8:10])-[#6:8]2:[#6:3]-1:[#6:4]1:[#6:33]3:[#6:34]:[#6:35]:[#6:36]:[#6:37](-[Cl:38]):[#6:32]:3:[#7:20](\\[#6@:21]3-[#6@:30](/[#8:31])-[#6@@:28](\\[#8:29])-[#6@:26](/[#8:27])-[#6@@:23](\\[#6:24]-[#8:25])-[#8:22]-3):[#6:5]:1:[#6:6]1:[#7:19]:[#6:13]3:[#6:14](-[Cl:18]):[#6:15]:[#6:16]:[#6:17]:[#6:12]:3:[#6:7]:1:2>>[#8:1]=[#6:2]1-[#7:11]-[#6:9](=[#8:10])-[#6:8]2:[#6:3]-1:[#6:4]1:[#6:33]3:[#6:34]:[#6:35]:[#6:36]:[#6:37](-[Cl:38]):[#6:32]:3:[#7:20](\\[#6@:21]3-[#6@:30](/[#8:31])-[#6@@:28](\\[#8:29])-[#6@:26](/[#8:27]-[#6])-[#6@@:23](\\[#6:24]-[#8:25])-[#8:22]-3):[#6:5]:1:[#6:6]1:[#7:19]:[#6:13]3:[#6:14](-[Cl:18]):[#6:15]:[#6:16]:[#6:17]:[#6:12]:3:[#6:7]:1:2",
            "reactions": [
                {
                    "substrate": "O=C1NC(=O)c2c1c1c3cccc(Cl)c3[nH]c1c1c2c2cccc(Cl)c2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O",
                    "products": [
                        "CO[C@H]1[C@H](O)[C@@H](O)[C@H](n2c3c(Cl)cccc3c3c4c(c5c6cccc(Cl)c6[nH]c5c32)C(=O)NC4=O)O[C@@H]1CO"
                    ],
                    "isIntermediate": false,
                    "description": "4\u2032-O-methylation of 4\u2032-demethylrebeccamycin to rebeccamycin using SAM as the methyl donor."
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "Heterologous expression",
                    "In vitro assay",
                    "Knock-out studies",
                    "Site-directed mutagenesis"
                ],
                "references": [
                    "doi:10.1074/jbc.M800503200",
                    "doi:10.1074/jbc.m800503200",
                    "doi:10.1002/cbic.200500504"
                ]
            },
            "databaseIds": {
                "rhea": "27353",
                "ec": "2.1.1.164"
            }
        }
    ]
}