FMOC-L-CYCLOPROPYLGLYCINE Chemical Properties

Boiling point:

577.1±33.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.85±0.10(Predicted)

form 

powder

color 

White

optical activity

17.134°(C=0.01g/ml DCM)

InChI

InChI=1S/C20H19NO4/c22-19(23)18(12-9-10-12)21-20(24)25-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,21,24)(H,22,23)/t18-/m0/s1

InChIKey

YMLZBPTXRMNAFP-SFHVURJKSA-N

SMILES

C1(COC(=O)N[C@H](C(O)=O)C2CC2)C2C=CC=CC=2C2C=CC=CC=21

Safety Information

Hazard Codes 

Xi

HS Code 

2922498590

FMOC-L-CYCLOPROPYLGLYCINE Usage And Synthesis

Chemical Properties

White powder

Uses

Fmoc-L-cyclopropylglycine is used in preparation of tailored Cyclodepsipeptides as potent non-covalent serine protease inhibitors.

Synthesis

GENERAL STEPS: 2.3 g of Na2CO3 was dissolved in 34 mL of water and chloroformic acid-9-fluorenylmethyl ester and (S)-2-amino-2-cyclopropylacetic acid were added with stirring. The reaction mixture was stirred at room temperature. After completion of the reaction, the product was characterized by FT-IR and NMR.FT-IR (pure): 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm^-1.^1H NMR ( CDCl3, 600 MHz): δ = 7.76 (d, 2H, J = 7.2 Hz), 7.60-7.59 (m, 2H), 7.41-7.39 (m, 2H), 7.32-7.30 (m, 2H), 5.36 (d, 1H, J = 6 Hz), 4.45-4.39 (m, 2H), 4.24-4.21 (m, 1H ), 3.83-3.81 (m, 1H), 1.14-1.13 (m, 1H), 0.65-0.46 (m, 5H) ppm. ^13C NMR (CDCl3, 150 MHz): δ = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1 , 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm. HRMS (ESI): m/z [M + Na]^+ Calculated value C20H19NO4Na 360.1206, measured value 360.1193.

References

[1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1698 - 1708
[2] Patent: WO2016/138288, 2016, A1. Location in patent: Page/Page column 124

FMOC-L-CYCLOPROPYLGLYCINE(1212257-18-5)Related Product Information

• FMOC-ALA(BETA-CYCLOBUTYL)-OH
• FMOC-L-CYCLOPROPYLALANINE
• FMOC-L-CYCLOPENTYLGLYCINE
• Fmoc-cyclopropylglycine
• FMOC-D-CYCLOPROPYLGLYCINE
• L-Cyclopropylglycine