Protecting group chemistry for clean, reductant-free dyeing

A method of producing a compound of Formula (A), the method comprising:

• culturing a host cell in vitro in a growth medium,
• wherein the host cell is genetically modified with heterologous nucleic acids encoding:
• i) a heterologous oxygenase polypeptide comprising an amino acid sequence having at least 90% amino acid sequence identity to any one of SEQ ID NOs:1 and 21-24;
• and
• ii) a heterologous glucosyltransferase polypeptide comprising an amino acid sequence having at least 90% amino acid sequence identity to any one of SEQ ID NOs:3-8,
• wherein the compound of Formula (A) is:
• wherein:
• R1, R2, R3, and R4 are independently selected from the group consisting of H, halo, nitro, sulfate, phosphate, hydroxyl, —C(O)ORb, —R2C(O)ORb,
• —RaOC(O)Rb, —ORa, —NRbRc, and alkyl;
• wherein alkyl is unsubstituted or substituted with one or more substituents independently selected from the group consisting of halo, nitro, sulfate, phosphate, hydroxyl, —C(O)ORb, —RaC(O)ORb, —RaOC(O)Rb, —ORa, —NRbRc, and —RaORd;
• R5 is H or alkyl, wherein alkyl is unsubstituted or substituted with one or more substituents independently selected from the group consisting of halo, hydroxyl, ═O,
• —C(O)ORb, —RaC(O)ORb, —RaOC(O)Rb, —ORa, and —NRbRc;
• Ra and Rd are independently alkyl;
• Rb and Rc are independently H or alkyl;
• Z is a glycone;
• wherein the heterologous oxygenase polypeptide and the heterologous glucosyltransferase polypeptide are encoded by multiple heterologous nucleic acids, or wherein the heterologous oxygenase polypeptide and the heterologous glucosyltransferase polypeptide are encoded by a single heterologous nucleic acid.