{
    "accession": "MITE0000433",
    "status": "active",
    "comment": "Chlorination of tryptophan to 6-chlorotryptophan",
    "changelog": [
        {
            "version": "1",
            "date": "2026-06-25",
            "contributors": [
                "0009-0008-8086-5325"
            ],
            "reviewers": [
                "0000-0001-5701-0590"
            ],
            "comment": "New entry."
        }
    ],
    "enzyme": {
        "name": "ThdH",
        "description": "Tryptophan 6-halogenase",
        "references": [
            "doi:10.1002/cbic.201400016",
            "doi:10.1002/anie.7072895"
        ],
        "auxiliaryEnzymes": [
            {
                "name": "ThdF",
                "description": "Flavin reductase",
                "databaseIds": {
                    "uniprot": "UPI000814E025",
                    "genpept": "ANW12119.1"
                }
            }
        ],
        "databaseIds": {
            "uniprot": "UPI0000EA332E",
            "genpept": "ANW12118.1",
            "mibig": "BGC0001374"
        },
        "cofactors": {
            "organic": [
                "FAD"
            ]
        }
    },
    "reactions": [
        {
            "tailoring": [
                "Halogenation"
            ],
            "description": "ThdH catalyzes regioselective chlorination of L-tryptophan at the C6 position of its indole ring during the biosynthesis of thienodolin",
            "reactionSMARTS": "[#7:1]\\[#6@:2](-[#6:13](-[#8:15])=[#8:14])-[#6:3]-[#6:4]1:[#6:8]2:[#6:9]:[#6:10]:[#6:11]:[#6:12]:[#6:7]:2:[#7:6]:[#6:5]:1>>[#7:1]\\[#6@:2](-[#6:13](-[#8:15])=[#8:14])-[#6:3]-[#6:4]1:[#6:8]2:[#6:9]:[#6:10]:[#6:11](-[Cl]):[#6:12]:[#6:7]:2:[#7:6]:[#6:5]:1",
            "reactions": [
                {
                    "substrate": "N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O",
                    "products": [
                        "N[C@@H](Cc1c[nH]c2cc(Cl)ccc12)C(=O)O"
                    ],
                    "isIntermediate": true,
                    "description": "Tryptophan 6-halogenase ThdH, could catalyze the regioselective chlorination, as well as bromination, of tryptophan to form 6-chlorotryptophan and 6-bromotryptophan which leds to the production of thienodolin and 6-bromothienodolin, respectively."
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "Heterologous expression",
                    "Knock-out studies"
                ],
                "references": [
                    "doi:10.1002/cbic.201400016"
                ]
            }
        }
    ]
}