Hentriacontanonaene

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Hentriacontanonaene
Hentriacontanonaene.png
Names
IUPAC name
(3Z,6Z,9Z,12Z,15Z,19Z,22Z,25Z,28Z)-Hentriaconta-3,6,9,12,15,19,22,25,28-nonaene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C31H46/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29,31H,3-4,9-10,15-16,21-22,27-28,30H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-
    Key: QBQCAYTWEQRERN-VHUCEKMMSA-N
  • CC\C=C/C\C=C/C\C=C/C\C=C/CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
Properties
C31H46
Molar mass 418.709 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hentriacontanonaene is a long-chain polyunsaturated hydrocarbon produced by numerous gamma-proteobacteria primarily from the marine environment. Hentriacontanonaene was originally isolated from bacterial isolates from Antarctic sea ice cores. [1] All isolated bacteria that produced hentriacontanonaene also produced the polyunsaturated fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). [1] [2] Given its polyunsaturated nature it has been proposed that this molecule is produced as part of a response to maintain optimal membrane fluidity. [1] [3]

Biosynthesis

The biosynthesis of this compound was initially identified by its similarity to other known pathways found in bacteria that produce similar long-chain hydrocarbons. [4] Production of monounsaturated and tri-unsaturated long-chain hydrocarbons in various microbial lineages has been attributed to the oleABCD gene cluster. [3] In this pathway two acyl-CoA or acyl-ACP are condensed using a non-decarboxylative Claisen condensation to yield a β-keto-thioester. [5] Hydrolysis from the enzyme is followed by reduction of the β-keto group to an alcohol catalyzed by an NADPH dependent reductase OleD. [6] The remaining steps include decarboxylation and dehydration, which might be combined as a single decarboxylation elimination step. [6] The exact roles of OleB and OleC in this pathway are unknown, however deletion of oleC yielded a strain that produced a mono-ketone product without the completed olefin. [3]

The overall unsaturation of the compound is determined by the acyl precursors and it has been hypothesized that condensation of two 16:4(n-3) acyl chains by OleABCD yields hentriacontanonaene. [2] [3] [4] A polyketide-like pathway responsible for the production of eicosapentaenoic acid provides the polyunsaturated precursor for hentriacontanonaene. [3]

Hentriacontanonaene biosynthetic pathway Hentriacontanonaene biosynthetic pathway.png
Hentriacontanonaene biosynthetic pathway

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References

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