Isoprene → 2-Methyl-3-buten-2-ol
Reaction equation
[O:1]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])P(OP([O-])([O-])=O)(=O)[O-].[CH2:15]=[CH:16][C:17](=[CH2:19])[CH3:18]>>[CH3:13][C:12]([CH3:14])=[CH:11][CH2:10][OH:1].[CH3:19][C:17]([OH:1])([CH:16]=[CH2:15])[CH3:18]Participants
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.
Sources & evidence
- ORD record
- ord-de0608e622e547e7941bd7089040b36f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741613B2
Reaction notes
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