FMOC-SER-OME

FMOC-SER-OME Property

Boiling point:

579.4±45.0 °C(Predicted)

Density 

1.285±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

form 

Solid

pka

10.07±0.46(Predicted)

color 

White to off-white

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

FMOC-SER-OME Chemical Properties,Usage,Production

Chemical Properties

White to off-white powder

Uses

Fmoc-Ser-OMe (Fmoc-L-Ser-OMe) is a hydroxylated L-amino acid protected with a 9-fluorenylmethyloxycarbonyl (Fmoc) group. Fmoc-Ser-OMe involves in chlorophyll–amino acid conjugates synthesis, and acts as a chromo/fluorophores modified protein and emits visible to near-infrared lights efficiently. Fmoc-Ser-OMe glycosylates and produces small mucin-related Olinked glycopeptides, as an alcohol acceptor[1][2].

Synthesis

GENERAL STEPS: To a mixed solution of 1,4-dioxane (15 mL) and water (90 mL) containing L-serine methyl ester hydrochloride (10.0 g, 64.3 mmol), sodium bicarbonate (10.8 g, 129 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes. Subsequently, a solution of 1,4-dioxane (60 mL) of 2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate (21.7 g, 64.3 mmol) was slowly added to the reaction system, and stirring was continued at room temperature for 14 hours. Upon completion of the reaction, water was added to the reaction mixture and extracted three times with ethyl acetate. The organic layers were combined and washed sequentially with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Ether and heptane were added to the residue and the precipitate was collected by filtration to give fmoc-L-serine methyl ester (22.3 g, yield: quantitative). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 2.00-2.15 (1H, m), 3.81 (3H, s), 3.89-4.07 (2H, m), 4.20-4.28 (1H, m), 4.39-4.53 (3H, m), 5.63-5.74 (1H, m), 7.29-7.37 (2H , m), 7.38-7.46 (2H, m), 7.55-7.65 (2H, m), 7.74-7.82 (2H, m).

References

[1] Tamiaki H, et al. Synthesis of chlorophyll-amino acid conjugates as models for modification of proteins with chromo/fluorophores. Bioorg Med Chem. 2014 Feb 15;22(4):1421-8. DOI:10.1016/j.bmc.2013.12.059
[2] K?rkk?inen TS, et al. Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides. Carbohydr Res. 2008 Jul 21;343(10-11):1830-4. DOI:10.1016/j.carres.2008.03.034