FMOC-L-Methionine Chemical Properties

Melting point:

121-123 °C(lit.)

alpha 

-29 º (c=1,DMF 24 ºC)

Boiling point:

614.6±55.0 °C(Predicted)

Density 

1.2053 (rough estimate)

refractive index 

-29.5 ° (C=1, DMF)

storage temp. 

2-8°C

solubility 

very faint turbidity in Methanol

pka

3.72±0.10(Predicted)

form 

Granular Powder

color 

White

optical activity

[α]20/D -29.5±1.5°, c = 1% in DMF

BRN 

4300266

InChI

InChI=1S/C20H21NO4S/c1-26-11-10-18(19(22)23)21-20(24)25-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-12H2,1H3,(H,21,24)(H,22,23)/t18-/m0/s1

InChIKey

BUBGAUHBELNDEW-SFHVURJKSA-N

SMILES

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

CAS DataBase Reference

71989-28-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37/39-27-26

WGK Germany 

3

HS Code 

2930 90 98

MSDS

• Language:English Provider:FMOC-L-Methionine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

FMOC-L-Methionine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

N-Fmoc-L-methionine is an N-Fmoc-protected form of L-Methionine (M260440). L-Methionine is an essential amino acid that is obtained from our diet. L-Methionine can be found in grain legumes (such as lentils), and poultry. L-Methionine’s main function is to act as the primary “Start” sequence on mRNA so that the ribosomes can start translating the mRNA into proteins.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

Synthesis of Fmoc-L-methionine: 6 mmol of L-methionine and 6.3 mmol of 9-fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu) were dissolved in 20 mL of N,N-dimethylformamide (DMF). Subsequently, 6.3 mmol of sodium bicarbonate (NaHCO3) was added to the reaction mixture to neutralize the acid produced during the reaction and to remove the solvent and residual amines. The reaction mixture was stirred at 50 °C overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified to afford the target compound Fmoc-L-methionine in 78% yield.

References

[1] Patent: CN105622471, 2016, A. Location in patent: Paragraph 0019; 0020
[2] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983

FMOC-L-Methionine(71989-28-1)Related Product Information

• 1,1'-Carbonyldiimidazole
• DL-Methionine
• CARBONYL SULFIDE
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• Fmoc-Lys(Boc)-OH
• Zinc methionine sulfate
• Fmoc-Aib-OH
• Fmoc-Asp(OtBu)-OH
• 9-Fluorenylmethyl chloroformate
• Fmoc-Phe-OH
• L-Methionine
• Fmoc-Pro-OH
• Fmoc-OSu
• Fmoc-L-glutamic acid
• FMOC-L-Valine
• Fmoc-L-glutamic acid-gamma-benzyl ester
• Fmoc-L-hydroxyproline
• FMOC-CHG-OH