L-Serine → Arachidonic Acid

HRID 630595Notes

Reaction equation

N[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)NC=1.N[C@H:17]([C:22](O)=O)[CH2:18][CH:19]([CH3:21])C.O=[CH:26][C@@H:27]([C@H:29]([C@@H:31]([C@@H:33](CO)O)O)O)O.S(O)(O)(=O)=O.N1C(N)=C2C(N=CN2)=NC=1.N[C@H](C(O)=O)CCCNC(=N)N.N[C@H](C(O)=O)CC(O)=O.N[C@H](C(O)=O)CCC(O)=O.N[C@H](C(O)=O)CC1N=CNC=1.N[C@H](C(O)=O)CCCCN.N[C@H](C(O)=O)CCSC.N[C@H](C(O)=O)CC1C=CC=CC=1.N[C@H](C(O)=O)CO.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.N[C@H](C(O)=O)C(C)C.N[C@H](C(O)=O)[C@@H](C)O>>[C:13]([OH:15])(=[O:14])[CH2:2][CH2:3][CH2:4]/[CH:12]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:26]=[CH:27]\[CH2:29]/[CH:31]=[CH:33]\[CH2:22][CH2:17][CH2:18][CH2:19][CH3:21]

Participants

Reactant 15

HCID 5951L-Serine

HCID 5960L-Aspartic Acid

HCID 5962L-Lysine

HCID 6057L-Tyrosine

HCID 6106L-Leucine

HCID 6137L-Methionine

HCID 6140L-Phenylalanine

HCID 6287L-Valine

HCID 6288L-Threonine

HCID 6305L-Tryptophan

HCID 33032L-Glutamic Acid

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HCID 118738321-30-2

HCID 178418600HCID 178418600, compound

HCID 178419078HCID 178419078, compound

Product 1

HCID 444899Arachidonic Acid

Procedure

ARA3-1 strain was transformed with plasmids pYE22m, pYE-MALPLAT5, and pYE-MALPLAT6. Transformed strains were selected by viability on SC-Trp, Leu, Ura agar medium (2% agar) containing, per liter, 6.7 g Yeast nitrogen base w/o amino acids (DIFCO), 20 g glucose and 1.3 g amino acid powder (a mixture of 1.25 g adenine sulfate, 0.6 g arginine, 3 g aspartic acid, 3 g glutamic acid, 0.6 g histidine, 0.9 g lysine, 0.6 g methionine, 1.5 g phenylalanine, 11.25 g serine, 0.9 g tyrosine, 4.5 g valine, and 6 g threonine).

Workup

additioncontaining, per liter, 6.7 g Yeast nitrogen base

Sources & evidence

ORD record: ord-93b919772abc4c698d0b217648e1d666
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315835B2

Reaction notes

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