N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Tyrosine → N-(cis-5,8,11,14,17-Eicosapentaenoyl)-O-Phospho-L-Tyrosine

HRID 2185853

Reaction equation

HRID 2185853 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][CH2:19][CH3:20].C(O)(=O)CCC/C=C\CC=CCC=CCC=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]/[CH:5]=[CH:6]\[CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH:17]=[CH:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 70024297N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-TyrosineHCID 70198906Npc164440

Product 1

HCID 70173995N-(cis-5,8,11,14,17-Eicosapentaenoyl)-O-Phospho-L-Tyrosine

Procedure

This compound was prepared as described above for (8), using 0.5 mmol (151 mg) of cis-5,8,11,14,17-eicosapentaenoic acid; yield 65 mg, (24%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 1.5-1.6 (t, 2H, CH2); 2.0-2.2 (m, 6H, CH2CO and 2CH2CH═CH); 2.7-3.0 (m, 10H, 4HC═CH—CH2—CH═CH and CH2Ar); 4.3-4.4 (m, 1H, NHCHCO); 5.2-5.4 (br s, 10H, 5HC═CH); 7.1 (s, 4H, Ar); 8.2-8.4 (m, 3H, NH and 2POH)

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b658e57e73d84c25b9cb7729c8e62f53
Source dataset
uspto-grants-2002_06
Patent number
US06403554B2

Linked notes

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