FMOC-SER(AC)-OH Chemical Properties

Boiling point:

611.2±55.0 °C(Predicted)

Density 

1.322

storage temp. 

Sealed in dry,Room Temperature

pka

3.27±0.10(Predicted)

form 

Solid

color 

White to off-white

optical activity

-19.4°(C=0.01g/ml ETOH)

InChI

InChI=1S/C20H19NO6/c1-12(22)26-11-18(19(23)24)21-20(25)27-10-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-11H2,1H3,(H,21,25)(H,23,24)/t18-/m0/s1

InChIKey

HSGIKRPBGCJRDB-SFHVURJKSA-N

SMILES

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

FMOC-SER(AC)-OH Usage And Synthesis

Uses

Fmoc-Ser(Ac)-OH (Fmoc-O-acetyl-L-serine) is a Serine derivative. Fmoc-Ser(Ac)-OH can be used for the preparation of broad-spectrum coronavirus membrane fusion inhibitor[1].

Synthesis

General procedure for the synthesis of Fmoc-O-acetyl-L-serine from O-acetyl-L-serine and 9-fluorenylmethyl-N-succinimidyl carbonate: O-acetyl-L-serine (337 g, 1.0 mol) was dissolved in 10% aqueous sodium carbonate solution and stirred until completely dissolved. 9-Fluorenylmethyl-N-succinimidyl carbonate dissolved in ethyl acetate (340 to 3400 ml) was slowly added dropwise at 20-30°C for 30-60 minutes. After the dropwise addition was completed, the reaction was continued with stirring for 1-8 hours. After completion of the reaction, the excess 9-fluorenylmethyl-N-succinimidyl carbonate was separated and removed. The aqueous phase was acidified with hydrochloric acid to pH=1-2 and then extracted with ethyl acetate (30,000 ml). The organic phase was washed with water to remove residual hydrochloric acid and concentrated to give an oil. White crystals were precipitated from ethyl acetate by crystallization, filtered and dried to give 273.0 g of Nα-9-fluorenylmethoxycarbonyl-O-acetyl-L-serine in 74.0% overall yield. The product was 99.56% pure by HPLC, with a melting point of 161.5-162.2°C and specific optical rotation [α]D=-22.6 (c=1, DMF).

References

[1] Patent: CN107501127, 2017, A. Location in patent: Paragraph 0014; 0028; 0029; 0030

FMOC-SER(AC)-OH(171778-17-9)Related Product Information

• FMOC-SER(AC)-OH
• FMOC-THR(AC)-OH
• O-ACETYL-L-SERINE
• Fmoc-L-Serine