| Identification | More | [Name]
N-Fmoc-N'-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-D-lysine | [CAS]
150629-67-7 | [Synonyms]
FMOC-D-LYS(DDE)-OH
FMOC-L-LYS(DDE)
FMOC-L-LYS(DDE)-OH
FMOC-LYS(DDE)-OH
FMOC-LYSINE(DDE)-OH
FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-D-LYSINE
FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-L-LYSINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-D-LYSINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-L-LYSINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-EPSILON-[(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL]-D-LYSINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-EPSILON-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-L-LYSINE
N-ALPHA-FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLDINE)ETHYL-L-LYSINE
N-ALPHA-FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-D-LYSINE
N-ALPHA-FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-L-LYSINE
N-ALPHA-FMOC-N-EPSILON-1-[(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDINE)ETHYL]-L-LYSINE
N-ALPHA-FMOC-N-EPSILON-[1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEXYLIDENE)ETHYL]-D-LYSINE
N-ALPHA-FMOC-N-EPSILON-DDE-D-LYSINE
N(A)-fmoc-N(E)(4,4-dime.-2,6-dioxocyclo-hexylidene)et.-L-lys
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine
N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine | [Molecular Formula]
C31H36N2O6 | [MDL Number]
MFCD01862894 | [Molecular Weight]
532.63 | [MOL File]
150629-67-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
~80 °C (dec.) | [Boiling point ]
750.1±60.0 °C(Predicted) | [density ]
1.222±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
3.88±0.21(Predicted) | [color ]
White to Light yellow | [Optical Rotation]
2.6° (C=0.01 g/ml, MEOH) | [Major Application]
peptide synthesis | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29224190 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 |
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