Biotin → HCID 178473676, compound

HRID 2395214Notes

Reaction equation

HRID 2395214 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].[C:17]([OH:22])(=[S:21])[CH:18]([CH3:20])[OH:19]>FC(F)(F)C(O)=O>[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1].[C:17]([OH:22])(=[S:21])[CH:18]([CH3:20])[OH:19]

Participants

4

Reactant 2

HCID 171548BiotinHCID 178473673HCID 178473673, compound

Product 1

HCID 178473676HCID 178473676, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The biotin derivative was treated with trifluoroacetic acid (10 mL) and the solution was kept at room temperature for 0.5 hours. The solvent was removed in vacuo and the residue was dissolved in dimethyl formamide (2 mL) and made basic with triethylamine. To this solution was added 1 mmol of N-hydroxysuccinimide ester of thiolactic acid. The mixture was stirred overnight at room temperature. The solvent was removed in vacuo, the residue was redissolved in CHCl3 and washed with deoxygenated water to prevent oxidation of sulfhydryl groups. The solvent was removed in vacuo and the residue was column chromatographed on silica gel with CHCl3 /MeOH (9/1→8/1) to produce the conjugate, ##STR5## 1H NMR (CDCl3 +D2O): δ1.37-1.95 (m, 10H), 2.23 (t, 2H), 2.61-2.97 (m, 3H), 3.16 (q, 1H), 3.37-3.72 (m, 24H), 4.28 (m, 1H), 4.45-4.55 (m, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dimethyl formamide (2 mL)
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was redissolved in CHCl3
  5. washwashed with deoxygenated water
  6. customThe solvent was removed in vacuo
  7. customchromatographed on silica gel with CHCl3 /MeOH (9/1→8/1)
  8. customto produce the conjugate, ##STR5## 1H NMR (CDCl3 +D2O): δ1.37-1.95 (m, 10H), 2.23 (t, 2H), 2.61-2.97 (m, 3H), 3.16 (q, 1H), 3.37-3.72 (m, 24H), 4.28 (m, 1H), 4.45-4.55 (m, 1H)

Sources & evidence

ORD record
ord-971ea988ac8d40faa21b7893a7839ea0
Source dataset
uspto-grants-1998_09
Patent number
US05814521

Reaction notes

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