Tyramine → Biotin tyramine

HRID 1080604

Reaction equation

HRID 1080604 reaction equation
ON1C(=O)CCC1=O.[OH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[C@@H:24]2[C@@H:19]([NH:20][C:21]([NH:23]2)=[O:22])[CH2:18][S:17]1)=[O:11].[NH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.C(=O)(O)[O-].C([NH+](CC)CC)C>CN(C)C=O>[OH:11][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[C@@H:24]2[C@@H:19]([NH:20][C:21]([NH:23]2)=[O:22])[CH2:18][S:17]1)=[O:9].[NH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 5610TyramineHCID 11768884Triethylammonium hydrogen carbonateHCID 86743017n-Hydroxysuccinimide biotin

Product 1

HCID 86746652Biotin tyramine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

a solution of biotin-N-hydroxysuccinimide, 170 mg (0.5 mMoles), and tyramine (recrystallized from water), 68.5 mg (0.5 mMoles), in 25 ml dimethylformamide was treated with 10 ml of 1M triethylammonium bicarbonate, pH 7.5, and then heated at 50° C. for 3 hours.

Sources & evidence

ORD record
ord-faeda10b7c5f4ec387b48377ca0d058b
Source dataset
uspto-grants-1996_12
Patent number
US05583001

Linked notes

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