FMOC-DAB(BOC)-OH Chemical Properties

Melting point:

111-113℃

Boiling point:

670.9±55.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.79±0.10(Predicted)

color 

White to Off-White

optical activity

[α]20/546 14.5±1°, c = 1% in methanol

Water Solubility 

Slightly soluble in water.

BRN 

6250328

InChIKey

LIWKOFAHRLBNMG-FQEVSTJZSA-N

SMILES

C(O)(=O)[C@@H](NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)CCNC(OC(C)(C)C)=O

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

F 

10

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

FMOC-DAB(BOC)-OH Usage And Synthesis

Chemical Properties

White powder

Uses

Fmoc-Dab(Boc)-OH,

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid from di-tert-butyl dicarbonate and Fmoc-L-2,4-diaminobutyric acid was as follows: 50 g (146.8 mmol) of Fmoc-L-2,4-diaminobutyric acid was suspended in 700 mL of a mixed solvent of acetone and water (1:1, v/v/v/v/v) at 0-10 °C. 38.4 g (176 mmol) of di-tert-butyl dicarbonate was slowly added. Subsequently, the pH of the reaction system was adjusted to 7.5-8 with 0.5 N NaOH solution.After 4 h of reaction, 56 g of N-fluorenylmethoxycarbonyl-N'-tert-butoxycarbonyl-L-2,4-diaminobutyric acid was obtained by the treatment in a yield of 86.62% and a purity of 99.4% by HPLC. The structure of the product was confirmed by IR and NMR spectra as detailed in Figures 3 and 4 in the literature.

References

[1] Patent: CN105348147, 2016, A. Location in patent: Paragraph 0020
[2] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 10, p. 1915 - 1924
[3] European Journal of Medicinal Chemistry, 1995, vol. 30, # 2, p. 115 - 122

FMOC-DAB(BOC)-OH(125238-99-5)Related Product Information

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• (2S,2'S)-N-ALPHA-9-FLUORENYLMETHYLOXYCARBONYL-3-(N'-T-BUTYLOXYCARBONYL-AZIRIDIN-2'YL)-ALANINE
• FMOC-L-TRANSHOMOPRO(4-NHBOC)
• FMOC-(2S, 3S)-GLY-3-PIP(BOC)