N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Tyrosine → N-(cis-4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-L-Tyrosine

HRID 2185849Notes

Reaction equation

HRID 2185849 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:39](O)(=O)[CH2:40]C/C=C\CC=CCC=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]/[CH:4]=[CH:5]\[CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:39][CH3:40]

Participants

3

Reactant 2

HCID 70024297N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-TyrosineHCID 730132534,7,10,13,16,19-cis-Docosahexaenoic acid

Product 1

HCID 70023032N-(cis-4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-L-Tyrosine

Procedure

This compound was prepared as described above for (8) using 0.5 mmol (164 mg) of cis-4,7,10,13,16,19-docosahexaenoic acid; yield 74 mg, (26%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 2.0-2.1 (t, 2H, CH2CO); 2.2-2.4 (m, 4H, 2CH2CH═CH); 2.7-2.9 (br s, 10H, 5HC═CHCH2CH═CH); 2.9-3.1 (m, 2H, CH2Ar); 4.3-4.4 (m, 1H, NHCHCO); 5.2-5.4 (br s, 12H, 6HC═CH); 7.0-7.2 (q, 4H, Ar); 8.2-8.4 (m, 3H, NH and 2POH)

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-99b99e6d8d44437197e8f67d14a2a0a2
Source dataset
uspto-grants-2002_06
Patent number
US06403554B2

Reaction notes

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