(+)-BIOTIN-EPSILON-AMINOCAPROIC ACID Chemical Properties

Melting point:

220-230 °C (dec.)

Boiling point:

721.3±55.0 °C(Predicted)

Density 

1.200±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly)

pka

4.75±0.10(Predicted)

form 

Solid

color 

White

BRN 

706392

Stability:

Hygroscopic! Store Under Inert Atmosphere.

InChI

InChI=1S/C16H27N3O4S/c20-13(17-9-5-1-2-8-14(21)22)7-4-3-6-12-15-11(10-24-12)18-16(23)19-15/h11-12,15H,1-10H2,(H,17,20)(H,21,22)(H2,18,19,23)/t11-,12-,15-/m0/s1

InChIKey

CMUGHZFPFWNUQT-HUBLWGQQSA-N

SMILES

C(O)(=O)CCCCCNC(=O)CCCC[C@H]1[C@@]2([H])NC(=O)N[C@@]2([H])CS1

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

(+)-BIOTIN-EPSILON-AMINOCAPROIC ACID Usage And Synthesis

Chemical Properties

White Solid

Uses

amine reactive biotinylation reagent

Uses

An active Biotinylation reagent

Biological Activity

Biotinyl-6-aminohexanoic acid (Biotin-X) may be used in the biosynthesis of biotinylated oligosaccharides. Biotinyl-6-aminohexanoic acid is frequently used as a derivative of N-hydroxysuccinimide ester.

Synthesis

The general procedure for the synthesis of N-biotinocaproic acid from 2,5-dioxopyrrolidin-1-yl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate and 6-aminohexanoic acid is as follows: ε-aminohexanoic acid (966 mg, 8.4 mmol) was dissolved in 30 mL of 1 M NaHCO3 aqueous solution . Subsequently, N-hydroxysuccinimide biotin (3.09 g) dissolved in 35 mL of DMF was slowly added dropwise to this solution and the reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, some of the solvent was removed by concentration under reduced pressure, then 150 mL of aqueous citric acid (100 g/L) was added and stirred at 60 °C for 30 min. The precipitate was collected by filtration and washed with distilled water. The resulting precipitate was dissolved in a solvent mixture of isopropanol and water (8:2, v/v) and stored at 4 °C to finally obtain pure N-biotin hexanoic acid (1.455 g, 50% yield) as pale yellow crystals. The product was detected by IR (KBr) showing characteristic absorption peaks: 3200-3500, 3070, 2932, 2859, 1696, 1644, 1543, 1475, 1391, 1324, 1265, 1118 cm-1. 1H NMR (600 MHz, DMSO-d6) data: δ 7.75 (1H, t, J = 5.4 Hz, C6-NH), 6.45 (1H, s, C13-NH), 6.38 (1H, s, C14-NH), 4.35-4.27 (1H, m, H-14), 4.12 (1H, m, H-13), 3.09 (1H, m, H-12), 3.00 (1H, m, H-6), 2.82 (1H, dd, J = 12.4, 5.1 Hz, H-15a), 2.57 (1H, d, J = 12.4 Hz, H-15b), 2.19 (2H, t, J = 7.4 Hz, H-2), 2.04 (2H, t, J = 7.3 Hz, H-8), 1.20-1.67 (14H, m).13C NMR (150 MHz, DMSO-d6) data: δ 171.84 (C-1, C-7), 162.74 (C-16), 61.06 (C-13), 59.20 (C-14), 55.44 (C-12), 39.68 (C-15), 38.25 (C-6), 35.21 (C-8), 29.05 (C-2), 28.92, 28.21, 28.04, 26.04, 25.73, 25.36.

References

[1] Chemical Communications, 2009, # 33, p. 5030 - 5032
[2] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 219 - 228
[3] RSC Advances, 2018, vol. 8, # 57, p. 32775 - 32793

(+)-BIOTIN-EPSILON-AMINOCAPROIC ACID(72040-64-3)Related Product Information

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