EZ-LINK (TM) PFP-BIOTIN, 50 MG Chemical Properties

Melting point:

190.0 to 194.0 °C

Boiling point:

555.3±50.0 °C(Predicted)

Density 

1.441

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

13.89±0.40(Predicted)

color 

White to Almost white

InChI

InChI=1S/C16H15F5N2O3S/c17-9-10(18)12(20)15(13(21)11(9)19)26-8(24)4-2-1-3-7-14-6(5-27-7)22-16(25)23-14/h6-7,14H,1-5H2,(H2,22,23,25)/t6-,7-,14-/m0/s1

InChIKey

DKTMDBQDSYQUEV-LEJLMFORSA-N

SMILES

C1(=O)N[C@]2([H])[C@H](CCCCC(OC3=C(F)C(F)=C(F)C(F)=C3F)=O)SC[C@]2([H])N1

CAS DataBase Reference

120550-35-8

Safety Information

HS Code 

2934.99.9001

EZ-LINK (TM) PFP-BIOTIN, 50 MG Usage And Synthesis

Description

Biotin-PFP ester will react with primary amino groups (-NH2) to form stable, irreversible amide bonds.

Uses

(+)-Biotin-PFP-ester is used to prepare melampomagnolide B as an antileukemic sesquiterpene.

Synthesis

GENERAL STEPS: D-Biotin (2.95 g, 12.00 mmol) was dissolved in N,N-dimethylformamide (DMF, 10 mL) to which pentafluorophenol (Pfp-OH, 2.80 g, 15.20 mmol) was subsequently added. A DMF solution (15 mL) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl, 5.70 g, 29.70 mmol) was slowly added dropwise to the above mixture over 30 min at 0 °C. After the dropwise addition, the reaction mixture was stirred overnight at room temperature under nitrogen atmosphere. Upon completion of the reaction, the product was washed with dichloromethane (DCM) to afford the target compound 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid perfluorophenyl ester in white powder form in 90% yield (4.50 g). The obtained product can be directly used in the subsequent reaction without further purification.1H NMR (D2O) data were as follows: δ 1.41-1.69 (m, 6H, CH2), 2.57 (d, 1H, CH2), 2.77-2.85 (m, 3H, CH2), 3.11-3.12 (m, 1H, CH), 4.14 (t, 1H, CH), 4.30 (t, 1H, CH), 6.37 (d, 2H, NH).

IC 50

Alkyl/ether

References

[1] Synthetic Communications, 1996, vol. 26, # 13, p. 2531 - 2547
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 7954 - 7955
[3] Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 8-9, p. 520 - 528
[4] Bioorganicheskaya Khimiya, 1994, vol. 20, # 8-9, p. 955 - 966
[5] Organic and biomolecular chemistry, 2003, vol. 1, # 6, p. 950 - 959

EZ-LINK (TM) PFP-BIOTIN, 50 MG(120550-35-8)Related Product Information

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