Alpha-Pinene is a monoterpene that may be a significant factor affecting bacterial activities in nature. It is a major component in tea-tree oils, and gives off a piney smelling odor. Terpenes are widely used as flavorings, deodorants, and medicines (as in the treatment of acne).
It is not clear whether the enzymes from B. pallidus here named "alpha-pinene dehydrogenase" and "alpha-pinene monooxygenase" are the same enzyme or two different enzymes. Indeed, these pathways may be catalyzed by a limited number of isomerase, monooxygenase and dehydrogenase enzymes with broad substrate specificities. Glycine mediates the isomerization of cis-2-Methyl-5-isopropylhexa-2,5-dienoic acid to trans-2-Methyl-5-isopropylhexa-2,5-dienoic acid. The beta-oxidation reactions transforming cis/trans-2-Methyl-5-isopropylhexa-2,5-dienoic acid to 3-Isopropylbut-3-enoic acid are postulated (Savithiry et al., 1998).
The following is a text-format alpha-Pinene pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions.
|-----------Graphical Map (12K)---------------------| Graphical Map (21K)
alpha-Pinene alpha-Pinene alpha-Pinene
Nocardia sp. Pseudomonas putida Pseudomonas putida
Pseudomonas fluorescens | Nocardia sp.
| | |
+---------------------+ | |
| | | |
| | | |
| | | |
| alpha-pinene | alpha-pinene | alpha-pinene | alpha-pinene mono-
| dehydrogenase | lyase | monooxygenase | oxygenase[NADH]
| | | |
| | | |
V V | V
Myrtenol Limonene | alpha-Pinene oxide
| | | |
| | | |
| | | |
| myrtenol | limonene | | alpha-pinene
| dehydrogenase | 6-monooxygenase | | oxide lyase
| | | +------------+
| | | |
V V V V
Myrtenal Carveol <-------- Pinocarveol cis-2-Methyl-5-iso- --> trans-2-Methyl-5-iso-
| | pinocarveol | propylhexa-2,5-dienal propylhexa-2,5-dienal
| | isomerase | | |
| | | | |
| myrtenal | carveol | pinocarveol | cis-2-methyl-5-iso- | trans-2-methyl-5-iso-
| dehydrogenase | dehydrogenase | dehydrogenase | propylhexa-2,5-dienal | propylhexa-2,5-dienal
| | | | dehydrogenase | dehydrogenase
| V | | |
V to the V V V
Myrtenic acid Limonene Pathway Pinocarvone cis-2-Methyl-5- trans-2-Methyl-5-
isopropylhexa-2,5- isopropylhexa-2,5-
dienoic acid dienoic acid
| |
| cis-2-methyl-5- | trans-2-methyl-5-
| isopropylhexa-2,5- | isopropylhexa-2,5-
| dienoate-CoA ligase | dienoate-CoA ligase
| |
v v
cis-2-Methyl-5- trans-2-Methyl-5-
isopropylhexa-2,5- isopropylhexa-2,5-
dienoyl-CoA dienoyl-CoA
| |
| enoyl-CoA hydratase | enoyl-CoA hydratase
| |
| |
+----> 3-Hydroxy-2,6- <---+
dimethyl-5-methylene-
heptanoyl-CoA
|
| 3-hydroxy-2,6-dimethyl-
| 5-methylene-heptanoyl-
| CoA dehydrogenase
|
v
2,6-Dimethyl-5-
methylene-3-oxo-
heptanoyl-CoA
|
| 2,6-dimethyl-5-methylene-
| 3-oxo-heptanoyl-CoA
| C-acetyltransferase
|
v
3-Isopropylbut-
3-enoyl-CoA
|
| 3-isopropylbut-
| 3-enoyl CoA
| thioesterase
|
v
3-Isopropylbut-3
enoic acid
Page Author(s): Diana Wong, Shiqian Li, Sean Anderson
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