Methods of making nylon intermediates from glycerol

Abstract

Embodiments of the invention relate to the enzymatic conversion of bioderived feedstocks to commercially valuable chemicals. The enzymatic conversions of the embodiments of the invention offer the potential for lower cost routes to these value-added chemicals. Some of the chemicals that are useful include nylon intermediates such as caprolactam, adipic acid, 1,6-hexamethylene diamine; butanediols such as 1,4-butanediol, 1,3-butanediol, and 2,3-butanediol; butanols such as 1-butanol, and 2-butanol; succinic acid, butadiene, isoprene, and 3-hydroxypropanoic acid.

1 . A method for converting glycerol enzymatically to alkane dicarboxylic acids, alkane diamines, alkane diols, ω-aminoacids, ω-hydroxyacids, alkanols, dienes or lactams in a genetically modified whole cell organism, wherein:
 (i) the whole cell organism expressing an active glycerol transporter protein, and 
 (ii) the alkane dicarboxylic acids, alkane diamines, alkane diols, ω-aminoacids, ω-hydroxyacids, alkanols, dienes or lactams are produced via a genetically modified pathway. 
 
     
     
         2 . The method of  claim 1 , wherein the alkane dicarboxylic acids are C4 to C6 alkane dicarboxylic acids. 
     
     
         3 . The method of  claim 1 , wherein the alkane dicarboxylic acid comprises hexane-1,6-dioic acid; the alkane diamine comprises hexane-1,6-diamine; the ω-aminoacids comprises 6-aminohexanoic acid; the lactams comprise caprolactam; and the dienes comprise 1,3-butadiene. 
     
     
         4 . The method of  claim 3 , wherein the hexane-1,6-dioic acid, hexane-1,6-diamine, 6-aminohexanoic acid, and caprolactam comprise intermediates in the synthesis of nylons. 
     
     
         5 . The method of  claim 1 , wherein the alkane diols comprise 1,3-propanediol, 1,4-butanediol, 1,3-butanediol or 2,3-butanediol; the ω-hydroxy acids comprise 3-hydroxypropionic acid or 4-hydroxybutanoic acid; and the alkanols comprise 1-butanol or 2-butanol. 
     
     
         6 . The method of  claim 1 , wherein the diene is 1,3-butadiene. 
     
     
         7 . A host cell capable of performing the method of  claim 1 . 
     
     
         8 . A recombinant host cell according to  claim 7 , which is genetically modified to overexpress a heterologous or homologous active glycerol transporter protein comprised of:
 (i) a bacterial glycerol major intrinsic protein (MIP) channel;   (ii) a plant tonoplast intrinsic protein (TIP) or an algae aquaporin; or   (iii) a fungi or yeast glycerol channel protein.   
     
     
         9 . A host cell according to  claim 7 , wherein the bacterial glycerol MIP channel is GipF. 
     
     
         10 . A host cell according to  claim 7 , wherein the active glycerol transporter protein is a plant TIP. 
     
     
         11 . A host cell according  claim 7 , wherein the active glycerol transporter protein is an algae aquaporin. 
     
     
         12 . A host cell according to  claim 7 , wherein the fungi or yeast glycerol channel protein is Fpsl. 
     
     
         13 . The host cell according to  claim 7 , wherein the host cell comprises  Yarrowia lipolytica, Candida  spp,  C. tropicalis, C. glycerinogenesis, C. albicans, C. cloacae, C. guillermondii, C. intermedia, C., maltosa, c. parapsilosis, C. zeylanoides, Aspergillus  spp.  Saccharomyces  spp.  Rhodotorula  spp.  Rhizopus  spp.  Trichosporon  spp.  Lipomyces  spp.,  Clostridium  spp. Pseudomonas  spp, or  Escherichia coli.    
     
     
         14 . The method of  claim 1 , wherein the glycerol has been produced as the by-product of bio-diesel production. 
     
     
         15 . A host cell according to  claim 7 , further comprising an aldehyde dehydrogenase and an aminotransferase that convert glycerol into aminohexanoic acid via a hexane-1,6 dioic acid intermediate. 
     
     
         16 . A host cell according to  claim 7 , comprising a metabolic pathway that converts glycerol into 6-aminohexanoic acid and further comprises an amidohydrolase to convert 6-aminohexanoic acid to caprolactam. 
     
     
         17 . A host cell according to  claim 7 , comprising a metabolic pathway that converts glycerol into 6-aminohexanoic acid and further comprises an aldehyde dehydrogenase and an aminotransferase or a diamine transaminase that convert 6-aminohexanoic to hexane-1,6-diamine. 
     
     
         18 . A host cell according to  claim 6 , which comprises acetyl-CoA C-acetyltransferase (EC 2.3.1.9), 3-hydroxybutyryl-CoA dehydrogenase (EC 1.1.1.157), and oxidoreductase[EC 1.1.1.-], wherein the cell produces 1,3-butandiol from glycerol. 
     
     
         19 . A host cell according to  claim 6 , which comprises acetolactate synthase (EC 2.2.1.6), Acetolactate decarboxylase (EC 4.1.1.5), and butanediol dehydrogenase (EC 1.1.1.4), wherein the cell produces 2,3-butandiol from glycerol.