Trifluoroacetic acid → Fmoc-Lys(biotinyl)-OH

HRID 394496Notes

Reaction equation

HRID 394496 reaction equation
[NH:1]([C:11]([O:13][CH2:14][CH:15]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].FC(F)(F)C(O)=O.C([SiH](C(C)C)C(C)C)(C)C.[OH:45][C:46]([CH2:48][CH2:49][CH2:50][CH2:51][C@H:52]1[C@@H:60]2[C@@H:55]([NH:56][C:57]([NH:59]2)=[O:58])[CH2:54][S:53]1)=O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN1C(=O)CCC1>[NH:1]([C:11]([O:13][CH2:14][CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:46]([CH2:48][CH2:49][CH2:50][CH2:51][C@H:52]1[C@@H:60]2[C@@H:55]([NH:56][C:57]([NH:59]2)=[O:58])[CH2:54][S:53]1)=[O:45]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 138754Silane, tris(1-methylethyl)-HCID 171548BiotinHCID 7010557(2S)-6-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

Product 1

HCID 11039242Fmoc-Lys(biotinyl)-OH

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Fmoc-Lys (mtt)-Resin was stirred with a mixture of 1% trifluoroacetic acid (TFA) and 0.1% triisopropylsilane (TIS) in DCM at 0° C. for 30 min and then for one hour at room temperature. Then, the resin was washed with NMP and DCM, and dried in vacuum. 2.68 gr. of loaded resin were obtained. This resin was then swelled with 25 ml NMP in the Presence of 930 mg Biotin, 1.44 gr. O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluophosphate (HBTU), 513 mg N-hydroxybenzotriazole (HOBt) and 1 ml of diisopropylethylamine (DIEA). The reaction was stirred for 4.5 hr. Then, the resin was washed with NMP and DCM, and dried in vacuum. 2.8 gr. of Fmoc-Lys(Biotin)-resin were obtained.

Workup

  1. washThen, the resin was washed with NMP and DCM
  2. customdried in vacuum
  3. customof loaded resin were obtained
  4. washThen, the resin was washed with NMP and DCM
  5. customdried in vacuum

Sources & evidence

ORD record
ord-22dad0b7c3cc4d3faa07e200c8ef0318
Source dataset
uspto-grants-2003_08
Patent number
US06602852B1

Reaction notes

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