9,12,15-cis-Octadecatrienoic acid → N-(cis-9,12,15-Octadecatrienoyl)-O-Phospho-L-Tyrosine

HRID 650795Notes

Reaction equation

HRID 650795 reaction equation
[C:1]([NH:22][C@H:23]([C:36]([OH:38])=[O:37])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][P:32]([OH:35])([OH:34])=[O:33])=[CH:27][CH:26]=1)(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18]CC.C(O)(=O)CCCCCCC/C=C\CC=CCC=CCC>>[C:1]([NH:22][C@H:23]([C:36]([OH:38])=[O:37])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][P:32]([OH:35])([OH:34])=[O:33])=[CH:27][CH:26]=1)(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH:12]=[CH:13][CH2:14][CH:15]=[CH:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 4456409,12,15-cis-Octadecatrienoic acidHCID 70024297N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Tyrosine

Product 1

HCID 70023957N-(cis-9,12,15-Octadecatrienoyl)-O-Phospho-L-Tyrosine

Procedure

This compound was prepared as described above for (8), using 0.5 mmol (139 mg) of cis-9,12,15-octadecatrienoic acid; yield 52 mg (20%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0,9-1.0 (t, 3H, ω-CH3); 1.3(s, 8H, 4CH2); 1.4-1.5(br s, 2H, CH2CH2CO); 2.0-2.2 (m, 6H, CH2CO and 2CH2CH═CH); 2.7-2.9 (br s, 4H, 2HC═CH—CH2—CH═CH ); 2.9-3.1 (m, 2H, CH2Ar); 4.3-4.4 (m, 1H, NHCHCO); 5.2-5.4 (br s, 6H, 3HC═CH); 7.0 (s, 4H, Ar); 8.2-8.4 (m, 3H, NH and 2POH).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-abcadb41cc944beda7a3c6add85fde5a
Source dataset
uspto-grants-2001_08
Patent number
US06274747B1

Reaction notes

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