Fmoc-L-Glutamic acid 1-tert-butyl ester Chemical Properties

Melting point:

78-80 °C

Boiling point:

638.1±55.0 °C(Predicted)

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

4.46±0.10(Predicted)

color 

White to off-white

InChIKey

GOPWHXPXSPIIQZ-FQEVSTJZSA-N

SMILES

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

CAS DataBase Reference

84793-07-7(CAS DataBase Reference)

Safety Information

HS Code 

29224290

Fmoc-L-Glutamic acid 1-tert-butyl ester Usage And Synthesis

Chemical Properties

White powder crystal

Uses

Fmoc-L-Glutamic acid 1-tert-butyl ester is most often used in peptide synthesis.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

(S)-4-Amino-5-tert-butoxy-5-oxovaleric acid (1.50 g, 7.38 mmol) was dissolved in 1,4-dioxane (40 mL) and cooled to 0 °C. An aqueous solution of sodium carbonate (196 mg, 1.85 mmol) (20 mL) and Fmoc-Cl (2.11 g, 8.16 mmol) were added sequentially. The reaction mixture was slowly warmed to room temperature and stirred for 16 hours. Upon completion of the reaction, the pH was adjusted to slightly acidic (pH ≈ 6) with 2 M hydrochloric acid, and the pH was adjusted with 1 M citric acid (ca. 80 mL) to ca. 3. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a 3:2 solvent mixture of ethyl acetate/hexane to afford (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (3.10 g, 99%) as a white solid.1H NMR (300 MHz, CDCl3) δ: Carboxylic acid peak (1H) not observed (due to broad signal), 7.76 (d, J = 7.5 Hz, 2H), 7.61-7.58 (m, 2H), 7.42-7.26 (m, 4H), 5.45 (d, J = 7.8 Hz, 1H), 4.48-4.19 (m, 4H), 2.51-2.34 (m, 2H), 2.28-2.14 (m, 1H), 1.99 -1.88 (m, 1H), 1.47 (s, 9H); ESI MS m/z = 448 [M + Na]+.

References

[1] Patent: US2014/274951, 2014, A1. Location in patent: Paragraph 0373; 0374

Fmoc-L-Glutamic acid 1-tert-butyl ester(84793-07-7)Related Product Information

• CARBONYL SULFIDE
• L-Glutamic acid
• Fmoc-Aib-OH
• 1,1'-Carbonyldiimidazole
• 9-Fluorenylmethyl chloroformate
• Fmoc-L-glutamic acid 5-tert-butyl ester
• FMOC-D-ALLO-THR-OH
• FMOC-D-CHA-OH
• Fmoc-N-Me-Lys(Boc)-OH
• Fmoc-Asp(OtBu)-OH
• FMOC-D-HOMOPHENYLALANINE
• FMOC-L-HOMOPHENYLALANINE
• FMOC-CHA-OH
• Fmoc-D-Aspartic acid beta-tert-butyl ester
• Fmoc-Leu-OH
• Fmoc-OSu
• Glutamic acid
• Fmoc-THr(Bzl)-OH