Fmoc-L-Lys(Dde)-OH Chemical Properties

Melting point:

~80 °C (dec.)

Boiling point:

750.1±60.0 °C(Predicted)

Density 

1.222±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.88±0.21(Predicted)

color 

White to Light yellow

optical activity

2.6° (C=0.01 g/ml, MEOH)

InChIKey

ZPSRBXWVBNVFTO-VWLOTQADSA-N

SMILES

C(O)(=O)[C@H](CCCCN/C(=C1/C(=O)CC(C)(C)CC/1=O)/C)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

CAS DataBase Reference

150629-67-7(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-L-Lys(Dde)-OH Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

The amino-protecting group Dde is orthogonal to both Fmoc and Boc protection and therefore useful to enable extension from lysine side chains by using Fmoc-tBu solid-phase methodologies.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

GENERAL STEPS: N-α-Fmoc-N-ε-Boc-L-lysine (5.66 g, 12.1 mmol) was dissolved in 4 M HCl/dioxane (120 mL) and stirred at room temperature for 2 h to remove the tert-butoxycarbonyl protecting group. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The resulting residue was dissolved in ethanol (60 mL) followed by the addition of 2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione (3.36 g, 18.4 mmol) and N,N-diisopropylethylamine (6.2 mL, 35.6 mmol). The reaction mixture was heated to reflux for 17 hours. After cooling to room temperature, the solvent was removed by concentration under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed sequentially with 1 M HCl (100 mL) and saturated saline (100 mL), and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (0.5%-3% methanol/dichloromethane gradient elution) to afford N-fluorenylmethoxycarbonyl-N'-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-lysine (2.64 g, 41% yield) as a white solid. The spectral data of the product were consistent with those reported in the literature.1H NMR (500 MHz, CDCl3): δ 13.31 (br s, 1H), 7.75 (d, J = 7.8 Hz, 2H), 7.59 (t, J = 7.8 Hz, 2H), 7.38 (t, J = 7.8 Hz, 2H), 7.31-7.28 (m, 2H), 5.73 (d, J = 8.0 Hz, 1H), 4.48-4.45 (m, 1H), 4.37 (d, J = 7.1 Hz, 2H), 4.20 (t, J = 7.1 Hz, 1H), 3.43-3.40 (m, 2H), 2.55 (s, 3H), 2.36 (s, 4H), 2.00-1.50 (m, 6H), 1.01 (s, 6H). HR-MS (m/z, FAB): calculated C31H37N2O6 ([M+H]+), 533.2652; measured, 533.2643.

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1227 - 1234

Fmoc-L-Lys(Dde)-OH(150629-67-7)Related Product Information

• Fmoc-N'-methyltrityl-L-lysine
• CARBONYL SULFIDE
• Fmoc-Phe-OH
• 9-Fluorenylmethyl chloroformate
• Selenium dioxide
• FMOC-LYS-OH
• DIOXOPROMETHAZINE HCL
• 1,4-Dioxane
• Fmoc-Asp(OtBu)-OH
• Fmoc-8-amino-3,6-dioxaoctanoic acid
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• Fmoc-Lys(Boc)-OH
• Nalpha-Fmoc-Ndelta-trityl-L-glutamine
• N,N-Dimethylcyclohexylamine
• Fmoc-Lys(Ddiv)-OH
• Fmoc-OSu
• FMOC-ARG(ME,PBF)-OH
• FMOC-ASU-OH