Borate → Biotin

HRID 374743Notes

Reaction equation

HRID 374743 reaction equation
[C:1](CCCCCN)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1.B([O-])([O-])[O-:23]>>[OH:23][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1)=[O:15]

Participants

3

Reactant 2

HCID 26574BorateHCID 22858230HCID 22858230, compound

Product 1

HCID 171548Biotin

Procedure

Biotinylpentylamine (0.001 mol) and isothiocyanatobenzyl-diethylenetriamine-pentaacetic acid (ITC-DTPA, 0.001 mol) are mixed together in borate buffer, 0.1M, pH 8, and stirred for 3 hours at room temperature. The biotin-DTPA is purified on a C-18 reverse-phase HPLC column run in an acetonitrile/water gradient. The acetonitrile is removed under reduced pressure on a rotary evaporator and the water by lyophilization to give a white powdery product. The structure, biotinylpentylamino-thioureaylbenzyl-DTPA (biotin-DTPA) is confirmed by mass spectral and micro analysis.

Workup

  1. customThe biotin-DTPA is purified on a C-18 reverse-phase HPLC column
  2. customThe acetonitrile is removed under reduced pressure on a rotary evaporator
  3. customthe water by lyophilization to give a white powdery product

Sources & evidence

ORD record
ord-2aee406fd45a4496adfbf3ee07d532d9
Source dataset
uspto-grants-1996_01
Patent number
US05482698

Reaction notes

Loading…