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Fmoc-L-Lys(Dde)-OH

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Fmoc-L-Lys(Dde)-OH Basic information
Product Name:Fmoc-L-Lys(Dde)-OH
Synonyms:FMOC-L-LYS(DDE);FMOC-L-LYS(DDE)-OH;FMOC-LYSINE(DDE)-OH;FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-D-LYSINE;(S)-2-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)-6-((1-(4,4-diMethyl-2,6-dioxocyclohexylidene)ethyl)aMino)hexanoic acid;N-Fmoc-N'-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-lysine;N-alpha-Fmoc-N-epsilon-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-lysine;N-ALPHA-(9-FLUOR
CAS:150629-67-7
MF:C31H36N2O6
MW:532.63
EINECS:
Product Categories:Fmoc-Amino Acids and Derivatives;amino acid;Amino Acids
Mol File:150629-67-7.mol
Fmoc-L-Lys(Dde)-OH Structure
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
pka3.88±0.21(Predicted)
form powder to crystal
color White to Light yellow
Optical Rotation2.6° (C=0.01 g/ml, MEOH)
Major Applicationpeptide synthesis
InChIKeyZPSRBXWVBNVFTO-VWLOTQADSA-N
SMILESC(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 Reference150629-67-7(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 2924 29 70
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
Fmoc-L-Lys(Dde)-OH Usage And Synthesis
Chemical PropertiesWhite to off-white crystalline powder
UsesThe 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 suitabilityreaction type: Fmoc solid-phase peptide synthesis
Synthesis
DDE-OH

94142-97-9

Fmoc-Lys(Boc)-OH

71989-26-9

Fmoc-L-Lys(Dde)-OH

150629-67-7

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 Preparation Products And Raw materials
Raw materialsDDE-OH-->2-ACETYLDIMEDONE-->FMOC-LYS-OH-->Ethanol-->Fmoc-Lys(Boc)-OH-->1,4-Dioxane-->N,N-Diisopropylethylamine-->Dimedone-->Hydrochloric acid
Tag: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