ChemicalBook CAS DataBase List TRANS-2,4-PENTADIENOIC ACID

TRANS-2,4-PENTADIENOIC ACID synthesis

7synthesis methods

Product Name:TRANS-2,4-PENTADIENOIC ACID
CAS Number:626-99-3
Molecular formula:C5H6O2
Molecular Weight:98.1

81357-28-0 Synthesis

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626-99-3
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Yield:-

Reaction Conditions:

with 3-hydroxypent-4-enoate dehydrataseEnzymatic reaction;

Steps:

1.2R
Figure 2 also shows pathways derived from the 4-hydroxy 2- oxovalerate intermediate. 4-hydroxy 2-oxovalerate is dehydrated to 2-oxopent-4- enoate (also called 2-hydroxypenta-2,4-dienoate) by 4-hydroxy-2-oxopentanoate dehydratase, also called 2-oxopent-4-enoate hydratase (2C). An alcohol dehydrogenase with 2-oxopent-4-enoate reductase activity forms 2-hydroxypent-4- enoate. Multiple enzymatic routes are shown in Fig 2 for converting 2-hydroxypent- 4-enoate to butadiene and butadiene precursors. One route entails isomerization of 2-hydroxypent-4-enoate to 5-hydroxypent-2-enoate (2E). This intermediate is then decarboxylated to 3-buten-l-ol (2P) and dehydrated to butadiene (2Q). Alternately, the 5-hydroxypent-2-enoate is further dehydrated to pentadienoate (2F) and subsequently decarboxylated to butadiene (2G). In yet another pathway, the 5- hydroxypent-2-enoate intermediate is activated to its corresponding acyl-CoA (21), dehydrated to pentadienoyl-CoA (2N), and further hydrolyzed to 2,4-pentadienoate (2J). Yet another set of pathways results when 2-hydroxypent-4-enoate is converted to 3-hydroxypent-4-enoate (abbreviated as 3FTPE) by a mutase (2H). Direct conversion of 3HPE to butadiene is catalyzed by an oxidative decarboxylase (2K). The two-step conversion of 3HPE to butadiene via 2,4-pentadienoate entails dehydration (2R) followed by decarboxylation (2G). In yet another route, 3HPE is activated to its acyl-CoA by a CoA synthetase or transferase. Conversion of 3-HPE- CoA to 2,4-pentadienoyl-CoA is catalyzed by an acyl-CoA dehydratase (20) or an isomerase and dehydratase (2M, 2 ). Useful products shown in Figure 2 include butadiene, 3-buten-l-ol, 4-hydroxy-2-oxovaIerate, 2-oxopent-4-enoate, 2- hydroxypent-4-enoate, 4-hydroxypent-2-enoate, 3HPE and 2,4-pentadienoate. Enzymes for catalyzing each step are described below.

References:

GENOMATICA, INC.;CULLER, Stephanie J.;BURK, Mark J.;OSTERHOUT, Robin E.;PHARKYA, Priti WO2016/4334, 2016, A1 Location in patent:Paragraph 0015; 00101

141-82-2 Synthesis