Background and overview[1]
Biotin-octapolyethylene glycol-amino group can be used as a pharmaceutical synthesis intermediate. If biotin-octapolyethylene glycol-amino is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell; if In case of eye contact, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
Apply[1]
Biotin-octapolyethylene glycol-amino application examples are as follows:
1) Synthesis of maleimide propionyl-PEG7-biotin:
To a stirred solution of biotin-octapolyethylene glycol-amino (1) (100 mg, 0.168 mmol) in anhydrous dichloromethane (7 mL) at room temperature under N2 was added maleimide NHS propionate (2) (49.2 mg, 0.186 mmol, 1.1 equiv). After stirring for 1 h, TLC analysis indicated completion of the reaction, at which time 1 N HCl (2 mL) was added. The organic solution was separated, washed with brine and dried over Na2SO4. The crude product obtained after evaporation under vacuum was purified by flash column chromatography on silica gel, eluting with a stepwise gradient of MeOH in dichloromethane (v/v = 1:30, 1:20 and 1:10) to The target compound, maleimidopropionyl-PEG7-biotin (3) (65 mg, 0.087 mmol, 52% yield) was provided as a waxy solid. 1HNMR(CDCl3)d7.01(brs,1H),6.96(brs,1H),6.70(s,2H),5.86(s,1H),5.06(s,1H),4.51(m,1H),4.33( m,1H),3.84(t,J＝7.2Hz,2H),3.62-3.66(m,24H),3.53(m,4H),3.40(m,4H),
3.15(m,1H),2.88-2.96(m,1H),2.73(d,J＝12.6Hz,1H),2.52(t,J＝7.2Hz,2H),2.24(t,J＝7.0 Hz,2H),1.66(m,4H),1.45(m,2H).
2) Synthesis of 2-fluoro-5-maleimidophenyl-PEG7-biotin:
Biotin-PEG7-NH2(1) (0.1g, 0.168mmol, 1 equivalent) and 2-fluoro-5-maleimidephenol NHS ester (6)( A mixture of 0.084 g, 0.252 mmol, 1.5 equiv) in dichloromethane (1 mL) was stirred overnight. The solvent was removed under vacuum, and the residue obtained was purified by LH20 column size exclusion chromatography (SEC), eluting with MeOH/dichloromethane (v/v 1:1), to afford the target product, 2, as an oil -Fluoro-5-maleimidophenyl-PEG7-biotin (7) (28 mg, 0.034 mmol, 20.5% yield), containing approximately 10% hydrolyzed form as shown by HPLC. An additional 90 mg mixture of the desired product and hydrolyzed form in a 3:2 ratio was also obtained.
Main reference materials
[1] CN201580053082.9 Method of conjugating polypeptides
