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US 12,098,405 B2Granted
Protecting group chemistry for clean, reductant-free dyeing
AssigneeThe Regents of the University of California
InventorsJohn Eugene Dueber, Zachary Nicholas Russ, Tammy Melody Hsu, Terry Don Johnson, Jr., Bernardo Cervantes, Ramya Lakshmi Prathuri, Shyam Pravin Bhakta, Arthur Muir Fong, III, Luke Nathaniel Latimer
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Abstract
The present disclosure relates to the biosynthesis of indigoid dye precursors and their conversion to indigoid dyes. Specifically, the present disclosure relates to methods of using polypeptides to produce indigoid dye precursors from indole feed compounds, and the use of the indigoid dye precursors to produce indigoid dyes.
Claims23
A method for dyeing a textile article, the method comprising:
- a) 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 comprising nucleotide sequences 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;
- b) converting the isolated compound of Formula (A) to a compound of Formula (II),
- wherein the compound of Formula (II) is:
- wherein R1, R2, R3, R4, and R5 are defined as for Formula (A);
- and
- c) applying the compound of Formula (II) to the textile article, thereby dyeing the textile article;
- 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.
20 more elements
A method for dyeing a textile article, the method comprising:
- a) 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 one or more heterologous nucleic acids comprising nucleotide sequences 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;
- b) converting the isolated compound of Formula (A) to a compound of Formula (II),
- wherein the compound of Formula (II) is:
- wherein R1, R2, R3, R4, and R5 are defined as for Formula (A);
- c) applying the compound of Formula (II) to the textile article;
- and
- d) converting the compound of Formula (II) to a compound of Formula (B), thereby dyeing the textile article, wherein the compound of Formula (B) is
- wherein R1, R2, R3, R4, and R5 are defined as for Formula (A), and
- R1′, R2′, R3′, R4′, and R5′ are R1, R2, R3, R4, and R5, respectively as defined in Formula (A).
21 more elements
A method for dyeing a textile article, the method comprising:
- a) 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 one or more heterologous nucleic acids comprising nucleotide sequences 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;
- b) converting the isolated compound of Formula (A) to a compound of Formula (II), wherein the compound of Formula (II) is:
- wherein R1, R2, R3, R4, and R5 are defined as for Formula (A);
- c) converting the compound of Formula (II) to a compound of Formula (B),
- wherein the compound of Formula (B) is
- wherein R1, R2, R3, R4, and R5 are defined as for Formula (A), and
- R1′, R2′, R3′, R4′, and R5′ are R1, R2, R3, R4, and R5, respectively as defined in Formula (A),
- d) reducing the compound of Formula (B) to provide a reduced intermediate of the compound of Formula (B),
- e) applying the reduced intermediate to the textile article, and
- f) oxidizing the reduced intermediate to a compound of Formula (B), thereby dying the textile article.
23 more elements
Dependencies are inferred from the claim text.