Reaction #487522

ord-6906d1b991c0473fb0c04a2367969762

Reaction equation

C=CC(=C)C
isoprene
C=CC(=C)C
isoprene
C=CC(=C)C
isoprene
CC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-]
dimethylallyl diphosphate
CC(C)=CCO
3-methyl-2-buten-1-ol
C=CC(C)(C)O
2-methyl-3-buten-2-ol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Although the direct conversion of dimethylallyl diphosphate to isoprene by isoprene synthase enzymes is known in the art, we have shown that isoprene can also be produced from two different alcohols, 3-methyl-2-buten-1-ol and 2-methyl-3-buten-2-ol, using linalool dehydratase-isomerase (see Example 1 and Example 2 and FIGS. 6 and 8), an enzyme isolated from Castellaniella defragrans strain 65Phen. The linalool dehydratase isomerase permits the development of novel isoprene biosynthetic pathways of either two or three steps. In a two-step isoprene biosynthetic pathway, dimethylallyl diphosphate is converted to 2-methyl-3-buten-2-ol by an enzyme such as a 2-methyl-3-buten-2-ol synthase, followed by conversion of 2-methyl-3-buten-2-ol to isoprene. In a three-step isoprene biosynthetic pathway, dimethylallyl diphosphate is converted to 3-methyl-2-buten-1-ol by either a phosphatase or a terpene synthase capable of converting dimethylallyl diphosphate to 3-methyl-2-buten-1-ol, 3-methyl-2-buten-1-ol is converted to 2-methyl-3-buten-2-ol by a 2-methyl-3-buten-2-ol isomerase, and 2-methyl-3-buten-2-ol is converted to isoprene by a 2-methyl-3-buten-2-ol dehydratase. As demonstrated in Example 1 and Example 2, the Castellaniella defragrans linalool dehydratase-isomerase functions as both a 2-methyl-3-buten-2-ol isomerase and a 2-methyl-3-buten-2-ol dehydratase.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741612B2uspto-grants-2014_06